Hubert Enterprises, Inc. and Subsidiaries v. Commissioner

125 T.C. No. 6

• Court: United States Tax Court
• Decided: September 21, 2005
• Docket: 4366-03, 10669-03, 16798-03
• Status: Unknown

Opinion

125 T.C. No. 6

UNITED STATES TAX COURT

HUBERT ENTERPRISES, INC. AND SUBSIDIARIES, ET AL.,1 Petitioners v. COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket Nos. 4366-03, 10669-03, Filed September 21, 2005. 16798-03.

A few individuals controlled a corporation (P1) and a limited liability company (ALSL). P1 transferred $2,440,684.38 to ALSL primarily to retransfer to a related limited partnership for use in the construction of a retirement community. The construction project was discontinued, and $2,397,266.32 of the transferred funds has not been repaid. P1 seeks to deduct those unrecovered funds as either a bad debt or a loss of capital/equity invested in ALSL. P2 had a subsidiary (S) that was a member of a limited liability company (L) that was involved in equipment leasing activities most of which arose in different years. Ps claim that the activities are aggregated under sec. 465(c)(2)(B)(i), I.R.C., into a single activity for the

1 Cases of the following petitioners are consolidated herewith: Hubert Enterprises, Inc. and Subs., docket No. 10669-03; and Hubert Holding Co., docket No. 16798-03. -2-

purpose of applying the at-risk rules of sec. 465, I.R.C. Ps also claim that S was at risk for portions of L’s losses by virtue of a deficit account restoration provision that, Ps state, made S liable for portions of L’s recourse obligations. Held: P1 may not deduct the unrecovered funds as either a bad debt or a loss of equity. Held, further, S may not aggregate all of L’s equipment leasing activities in that sec. 465(c)(2)(B)(i), I.R.C., treats as a single activity only those activities for which the equipment is placed in service in the same taxable year. Held, further, S may not increase its at-risk amounts on account of the deficit capital account restoration provision in that the provision was not operative in the relevant years.

William F. Russo and R. Daniel Fales, for petitioners.2

Gary R. Shuler, Jr., for respondent.

LARO, Judge: The Court has consolidated these cases for

trial, briefing, and opinion. In docket Nos. 4366-03 and

10669-03, Hubert Enterprises, Inc. (HEI), and Subsidiaries

petitioned the Court to redetermine respondent’s determination of

Federal income tax deficiencies of $974,805, $734,093, and

$1,542,820 in its taxable years ended July 27, 1997, August 3,

1998, and July 31, 1999, respectively (HEI’s 1997, 1998, and 1999

2 The petitions in these cases were filed with the Court by James H. Stethem (Stethem), Mark A. Denney (Denney), and R. Daniel Fales. Stethem later died and was withdrawn from the cases on Dec. 1, 2003. Denney withdrew from the cases on Feb. 2, 2005. William F. Russo entered his appearance in docket Nos. 4366-03 and 10669-03 on Feb. 11, 2004, and in docket No. 16798-03 on Mar. 15, 2004. -3-

taxable years, respectively). Respondent reflected these

determinations in notices of deficiency issued on December 17,

2002, and April 9, 2003, to HEI and its subsidiaries. Hubert

Holding Co. (HHC), HEI’s successor as parent of its affiliated

group, petitioned the Court in docket No. 16798-03 to redetermine

respondent’s determination of Federal income tax deficiencies of

$1,437,240 and $1,093,008 in its taxable years ended July 29,

2000, and July 28, 2001, respectively (HHC’s 2000 and 2001

taxable years, respectively). Respondent reflected this

determination in a notice of deficiency issued to HHC on June 30,

2003.

Following concessions by petitioners, we must decide the

following issues:

1. For HEI’s 1997 taxable year, whether HEI may deduct as

either a bad debt or as a loss of capital (equity) $2,397,266.32

of unrecovered funds that it transferred to Arbor Lake of

Sarasota Limited Liability Co. (ALSL), a limited liability

company of which HEI was not an owner but which was owned

primarily and controlled by a few individuals who also controlled

HEI. We hold HEI may not deduct the funds as either a bad debt

or a loss of capital; and

2. for HHC’s 2000 and 2001 taxable years, whether HHC may

deduct passthrough losses from leasing activities relating to

equipment placed in service in different taxable years. As an -4-

issue of first impression, petitioners claim that section

465(c)(2)(B)(i) aggregates these activities into a single

activity for purposes of applying the at-risk rules of section

465.3 Petitioners also claim that the members of the passthrough

entity, a limited liability company named Leasing Co., LLC (LCL),

were at risk for LCL’s losses by virtue of a deficit account

restoration provision that, petitioners state, made LCL’s members

liable for portions of LCL’s recourse obligations. We hold that

HHC may not deduct equipment leasing activity losses greater than

those allowed by respondent in the notice of deficiency.

FINDINGS OF FACT

Some facts were stipulated. We incorporate herein by this

reference the parties’ stipulation of facts and the exhibits

submitted therewith. We find the stipulated facts accordingly.

I. HEI

HEI was organized by the Hubert Family Trust (HFT) on or

about October 8, 1992. HEI’s only shareholder has always been

HFT. When HEI’s petitions were filed with the Court, its mailing

address was in Cincinnati, Ohio.

For HEI’s 1997, 1998, and 1999 taxable years, HEI was the

parent corporation of an affiliated group of corporations that

filed consolidated Federal corporate income tax returns. For

3 Unless otherwise noted, section references are to the applicable versions of the Internal Revenue Code, and Rule references are to the Tax Court Rules of Practice and Procedure. -5-

HEI’s 1997 and 1998 taxable years, the group’s other members,

each of which was wholly owned by HEI, were (1) Printgraphics,

Inc. (Printgraphics), (2) HBW, Inc. (HBW) (also known as Weber

Co.), (3) BES Manufacturing, d.b.a. Mr. Spray, (4) Vogt

Warehouse, Inc. (Vogt), (5) HGT, Inc. (HGT), (6) Hubert Co., and

(7) Graphic Forms and Labels, Inc. (Graphic). For HEI’s 1999

taxable year, the affiliated group of corporations in addition to

HEI consisted of the just-stated seven wholly owned subsidiaries

and two other wholly owned subsidiaries; namely, Public Space

Plus, Inc., and Hubert Development, Co.

From HEI’s organization through at least 1998, Howard Thomas

(Thomas) was HEI’s president, Edward Hubert was chairman of HEI’s

board of directors, George Hubert, Jr., was an HEI vice president

and secretary, Sharon Hubert was an HEI vice president, and J.

Gregory Ollinger (Ollinger) was an HEI vice president. From its

organization through August 1, 1998, HEI did not declare a

dividend or formally distribute any of its earnings and profits.

HEI’s undistributed earnings as of July 25, 1995, July 26, 1996,

August 2, 1997, and August 1, 1998, were $14,847,028,

$19,878,907, $25,164,181, and $31,298,257, respectively.

II. HHC

In August 1999, HEI transferred the stock of its

subsidiaries to HHC. For HHC’s 2000 and 2001 taxable years, HHC

was the parent corporation of an affiliated group of corporations -6-

that filed consolidated Federal corporate income tax returns.

For HHC’s 2000 taxable year, that affiliated group in addition to

HHC consisted of the nine subsidiaries that were members of the

HEI affiliated group in HEI’s 1999 taxable year. For HHC’s 2001

taxable year, the HHC affiliated group of corporations in

addition to HHC consisted of (1) Printgraphics, (2) HBW,

(3) Vogt, (4) HGT, and (5) Graphic. When HHC’s petition was

filed with the Court, its mailing address was in Cincinnati,

Ohio.

III. HFT

Thomas and Stethem are unrelated by blood or marriage to any

member of the Hubert family. Thomas and Stethem (sometimes

collectively, trustees) were HFT’s trustees. HFT’S settlors were

Anthony Hubert, Benjamin Hubert, Brian Hubert, Christopher

Hubert, Cynthia Hubert, Edward Hubert, George Hubert, Jr.,

Gregory Hubert, Joshua Hubert, Karen Hubert, Kathleen Hubert,

Kimberly Hubert, Robert Hubert, Scott Hubert, Sharon Hubert, and

Zachary Hubert (collectively, settlors). Edward Hubert, George

Hubert, Jr., and Sharon Hubert (collectively, controlling

settlors) have always held interests in HFT of 36.339 percent,

13.185 percent, and 16.488 percent, respectively. Anthony

Hubert, Benjamin Hubert, Christopher Hubert, Joshua Hubert, Karen

Hubert, Kathleen Hubert, Kimberly Hubert, Robert Hubert, Scott

Hubert, and Zachary Hubert have each always held interests in HFT -7-

of 3.095 percent. Brian Hubert, Cynthia Hubert, and Gregory

Hubert have each always held interests in HFT of 1.012 percent.

During their lives, the controlling settlors were to receive

annually all income attributable to their respective percentage

interests in the trust estate. Each of the other settlors was to

receive annually the income attributable to his or her trust

interest commencing as follows: (1) one-third at age 25,

(2) two-thirds at age 30, and (3) 100 percent at age 35.

Stethem died in 2003. He had been legal counsel for the

Hubert family and their companies. He drafted the trust

agreement (trust agreement) underlying HFT, and the settlors and

trustees executed the trust agreement on June 6, 1988. Under the

trust agreement, the trustees had the absolute discretion to

distribute HFT’s money, securities, or other property, either pro

rata or otherwise. The trust agreement also allowed the

controlling settlors, generally upon majority consent, to alter,

amend, or revoke the trust agreement. By amendments dated

December 30, 1988, and January 1, 1991, the settlors and the

trustees modified the trust agreement. Through the earlier

amendment, the Howard Thomas Trust acquired the rights and

privileges of a controlling settlor. Through the later

amendment, the Katherine Hubert Trust acquired the rights and

privileges of a controlling settlor. -8-

IV. ALSL

ALSL, also known as Seasons of Sarasota Limited Liability

Co., is a Wyoming limited liability company organized on

January 18, 1995. ALSL was organized to provide funds to a

limited partnership, Arbor Lake Development, Ltd. (ALD), to use

to construct a retirement condominium community in Sarasota,

Florida, to be known as the Seasons of Sarasota Retirement

Community (Seasons of Sarasota). For ALSL’s taxable years ended

December 31, 1995, 1996, and 1997, ALSL filed Federal partnership

returns of income. ALSL reported and had no revenue for those

years.

From January 18, 1995, through December 31, 1997, ALSL’s

units were owned as follows:

Member Units

Edward Hubert 20 George Hubert, Jr. 20 Sharon Hubert 20 Ollinger 5 Stethem 5 Sun Valley Investments 10 Thomas 20 100

According to the ALSL operating agreement, (1) ALSL and all of

its affairs were controlled by its members as a group, (2) the

members’ decisions by majority vote on the basis of membership

interests controlled, and (3) absent approval by a majority vote,

no single member had the power or authority to act on behalf of -9-

ALSL. During the relevant years, the owners of Sun Valley

Investments, a partnership, were Thomas and Stethem.

Pursuant to ALSL’s operating agreement, ALSL’s members were

required to contribute the following capital to ALSL:

Member Contribution

Edward Hubert $200 George Hubert, Jr. 200 Sharon Hubert 200 Ollinger 50 Stethem 50 Sun Valley Investments 100 Thomas 200 1000

None of ALSL’s members, with the exception of Thomas and Stethem,

ever contributed any capital to ALSL from his, her, or its own

funds. During 1996, Thomas and Stethem contributed $200,000 and

$50,000, respectively, to ALSL’s capital.4

As of December 31, 1995, ALSL reported for Federal income

tax purposes that it had cash of $7,298, that it owned a

$1,338,334 nonrecourse note receivable from ALD, and that it was

liable on a $1,345,684 nonrecourse note payable to HEI. ALSL

4 During HEI’s 1997 taxable year, Thomas was HEI’s most highly compensated officer, and Edward Hubert, George Hubert, Jr., and Sharon Hubert were its next three most highly compensated officers. During that year, HEI paid Thomas $420,922, and it paid $370,236 to each of the other three officers. During HEI’s 1998 taxable year, Thomas received significantly less compensation than these other three officers. During HEI’s 1998 taxable year, HEI paid Edward Hubert, George Hubert, Jr., Sharon Hubert, and Thomas $644,236, $894,236, $644,236, and $397,342, respectively. -10-

reported no other asset or liability as of that date, but for a

$52 bank charge which it elected to amortize over 60 months.

As of December 31, 1996, ALSL reported for Federal income

tax purposes that its sole asset was cash of $7,298 and that it

had no liabilities. ALSL also reported for Federal income tax

purposes that it had realized a $250,000 loss for 1996. ALSL

reported that the loss was attributable to “Defeasance of Debt

Income”, “Bad Debt Losses”, and “Miscellaneous Expenses” of

$2,345,685, negative $2,588,376, and negative $7,309,

respectively.

As of December 31, 1997, ALSL reported for Federal income

tax purposes that it had no assets, liabilities, or capital.

V. ALSL Note

Pursuant to a promissory note (ALSL note) dated January 18,

1995, ALSL (under the name Seasons of Sarasota Limited Liability

Co.) promised to pay HEI “$2,500,000.00, or so much thereof as

may be advanced and outstanding pursuant to any advances made by

the Lender to the Company.” The ALSL note was drafted as a

demand note without a fixed maturity date, and it stated that it

bore interest at a rate corresponding to the applicable Federal

rate. In connection with the ALSL note, HEI transferred a total

of $2,440,684.38 to ALSL from January 18, 1995, through March 6,

1997. ALSL then transferred those funds to ALD in connection

with a January 18, 1995, nonrecourse promissory note (ALD note) -11-

between ALD and ALSL. ALD would repay these transferred funds to

ALSL only upon the sale of condominium units in the Seasons of

Sarasota project, and ALSL would repay HEI only when and if it

received repayment from ALD. In December 1996, HEI decided not

to devote any more funds to the Seasons of Sarasota project.

In connection with the ALSL note, HEI transferred funds to

ALSL and ALSL made repayments to HEI as follows:

Date Amount Amount Repaid Unpaid Balance

1/18/95 $20,000.00 -0- $20,000.00 1/18/95 698.00 -0- 20,698.00 2/24/95 15,000.00 -0- 35,698.00 3/3/95 20,000.00 -0- 55,698.00 3/7/95 15,000.00 -0- 70,698.00 3/10/95 10,000.00 -0- 80,698.00 3/15/95 84,302.00 -0- 165,000.00 3/24/95 7,500.00 -0- 172,500.00 3/24/95 75,000.00 -0- 247,500.00 4/4/95 25,000.00 -0- 272,500.00 4/11/95 220,000.00 -0- 492,500.00 6/9/95 100,000.00 -0- 592,500.00 6/23/95 100,000.00 -0- 692,500.00 6/26/95 50,000.00 -0- 742,500.00 6/30/95 368.40 -0- 742,868.40 7/14/95 50,000.00 -0- 792,868.40 7/31/95 1,366.58 -0- 794,234.98 8/1/95 50,000.00 -0- 844,234.98 8/15/95 50,000.00 -0- 894,234.98 8/21/95 50,000.00 -0- 944,234.98 8/31/95 356.53 -0- 944,591.51 9/5/95 50,000.00 -0- 994,591.51 10/31/95 1,092.87 -0- 995,684.38 11/27/95 50,000.00 -0- 1,045,684.38 12/7/95 50,000.00 -0- 1,095,684.38 12/27/95 50,000.00 -0- 1,145,684.38 1/8/96 50,000.00 -0- 1,195,684.38 2/5/96 50,000.00 -0- 1,245,684.38 2/12/96 50,000.00 -0- 1,295,684.38 3/6/96 75,000.00 -0- 1,370,684.38 3/8/96 75,000.00 -0- 1,445,684.38 4/12/96 50,000.00 -0- 1,495,684.38 -12-

4/29/96 50,000.00 -0- 1,545,684.38 5/13/96 50,000.00 -0- 1,595,684.38 6/6/96 50,000.00 -0- 1,645,684.38 6/10/96 100,000.00 -0- 1,745,684.38 6/28/96 50,000.00 -0- 1,795,684.38 7/2/96 75,000.00 -0- 1,870,684.38 7/12/96 50,000.00 -0- 1,920,684.38 7/31/96 50,000.00 -0- 1,970,684.38 8/21/96 50,000.00 -0- 2,020,684.38 9/5/96 75,000.00 -0- 2,095,684.38 9/10/96 50,000.00 -0- 2,145,684.38 10/8/96 50,000.00 -0- 2,195,684.38 10/21/96 50,000.00 -0- 2,245,684.38 11/12/96 50,000.00 -0- 2,295,684.38 12/2/96 50,000.00 -0- 2,345,684.38 1/9/97 26,000.00 -0- 2,371,684.38 1/21/97 15,000.00 -0- 2,386,684.38 1/27/97 5,000.00 -0- 2,391,684.38 2/5/97 13,000.00 -0- 2,404,684.38 2/12/97 11,000.00 -0- 2,415,684.38 2/14/97 5,000.00 -0- 2,420,684.38 2/19/97 5,000.00 -0- 2,425,684.38 3/6/97 15,000.00 -0- 2,440,684.38 7/14/97 -0- $43,418.06 2,397,266.32

HEI did not establish a written schedule for repayment of any of

these transferred funds (or interest thereon), and HEI never

demanded that ALSL repay any of the funds (or interest thereon).

HEI never required that ALSL pledge any of its assets to secure

repayment of any of the transferred funds, and ALSL never pledged

any of its assets to secure such repayment. HEI never required

that ALSL’s members pledge security for repayment of any of the

transferred funds, and ALSL’s members never pledged any such

security. ALSL’s members never agreed to personally guarantee

repayment of any of the transferred funds.

On or as of July 31, 1996, HEI recorded on the ALSL note

that it was entitled to accrued interest of $93,200. This -13-

interest was never paid. HEI never accrued any other interest on

the HEI note.

The $43,418.06 payment that ALSL made to HEI on July 14,

1997, resulted from a reported liquidation of ALD’s assets in

1996.

VI. ALD

ALD was a Florida limited partnership formed on January 6,

1995, to develop the Seasons of Sarasota. ALD had one general

partner, ALSL, and one limited partner, James Culpepper

(Culpepper). Thomas was an ALD officer.

Pursuant to the ALD limited partnership agreement, ALSL was

to acquire a 97-percent interest in ALD in exchange for a $100

capital contribution, and Culpepper was to acquire a 3-percent

interest in ALD in exchange for a $100,000 capital contribution.

The limited partnership agreement stated that the percentages of

the partners’ interests in ALD did not have any relationship to

their respective capital contributions. Culpepper contributed

the referenced $100,000 in 1995. ALSL never contributed the

referenced $100 as such.

For its taxable years ended December 31, 1995, 1996, and

1997, ALD filed Federal partnership returns of income. ALD

reported and had no revenue for those years.

As of December 31, 1995, ALD reported on its 1995 return

that it had assets totaling $1,438,334 and a single liability of -14-

$1,338,334. The assets consisted of cash of $37,172, accounts

receivable of $1,714, deposits of $411,353, prepayments of

$11,505, work in progress of $567,705, depreciable assets of

$7,829, and intangible assets of $401,056. The single liability

was the $1,338,334 nonrecourse note payable to ALSL.

As of December 31, 1996, ALD reported on its 1996 return

that it had no assets or liabilities. On its 1996 return, ALD

wrote off its intangible assets and reported a liquidation of its

other assets.

As of December 31, 1997, ALD reported on its 1997 return

that it had no assets or liabilities.

VII. ALD Note

The ALD note was a promissory note dated January 18, 1995,

and payable to ALSL (under the name Seasons of Sarasota Limited

Liability Co.) in the amount of “$2,750,000.00, or so much

thereof as may be advanced and outstanding pursuant to any

advances made by the Lender to the Partnership.” The ALD note

was drafted as a demand note without a fixed maturity date, and

it stated that it bore interest at a rate corresponding to the

applicable Federal rate. In connection with the ALD note, ALSL

transferred a total of $2,690,531.88 to ALD from January 31,

1995, through March 31, 1997. ALSL transferred these funds to

ALD and ALD made a repayment to ALSL as follows: -15-

1/31/95 $20,698.00 -0- $20,698.00 2/28/95 19,442.85 -0- 40,140.85 2/28/95 10,570.73 -0- 50,711.58 3/31/95 82,500.00 -0- 133,211.58 3/31/95 5,000.00 -0- 138,211.58 3/31/95 101,825.86 -0- 240,037.44 4/30/95 25,000.00 -0- 265,037.44 4/30/95 220,000.00 -0- 485,037.44 6/30/95 100,000.00 -0- 585,037.44 6/30/95 100,000.00 -0- 685,037.44 6/30/95 368.40 -0- 685,405.84 6/30/95 50,000.00 -0- 735,405.84 7/5/95 112.40 -0- 735,518.24 7/28/95 50,000.00 -0- 785,518.24 7/31/95 1,366.58 -0- 786,884.82 8/1/95 50,000.00 -0- 836,884.82 8/15/95 50,000.00 -0- 886,884.82 8/21/95 50,000.00 -0- 936,884.82 8/31/95 356.53 -0- 937,241.35 9/5/95 50,000.00 -0- 987,241.35 9/15/95 50,000.00 -0- 1,037,241.35 10/3/95 50,000.00 -0- 1,087,241.35 10/4/95 564.00 -0- 1,087,805.35 10/9/95 58.28 -0- 1,087,863.63 10/16/95 50,000.00 -0- 1,137,863.63 10/24/95 470.59 -0- 1,138,334.22 10/27/95 50,000.00 -0- 1,188,334.22 11/30/95 50,000.00 -0- 1,238,334.22 12/7/95 50,000.00 -0- 1,288,334.22 12/27/95 50,000.00 -0- 1,338,334.22 1/31/96 50,000.00 -0- 1,388,334.22 2/29/96 50,000.00 -0- 1,438,334.22 2/29/96 50,000.00 -0- 1,488,334.22 3/31/96 50,000.00 -0- 1,538,334.22 3/31/96 50,000.00 -0- 1,588,334.22 3/31/96 75,000.00 -0- 1,663,334.22 4/30/96 50,000.00 -0- 1,713,334.22 4/30/96 75,000.00 -0- 1,788,334.22 5/31/96 50,000.00 -0- 1,838,334.22 6/30/96 200,000.00 -0- 2,038,333.22 7/31/96 175,000.00 -0- 2,213,334.22 8/31/96 50,000.00 -0- 2,263,334.22 9/30/96 125,000.00 -0- 2,388,334.22 10/31/96 100,000.00 -0- 2,488,334.22 11/30/96 50,000.00 -0- 2,538,334.22 12/31/96 50,000.00 -0- 2,588,334.22 -16-

1/31/97 7,197.66 -0- 2,595,531.88 1/31/97 46,000.00 -0- 2,641,531.88 2/28/97 34,000.00 -0- 2,675,531.88 3/31/97 15,000.00 -0- 2,690,531.88 7/10/97 5,000.00 $43,418.06 2,647,213.82

ALD used the transferred funds received from ALSL to pay

ALD’s operating expenses incurred in connection with the Seasons

of Sarasota project, including professional fees for site plans,

construction drawings, environmental assessments, surveying,

marketing studies, and expenses of the sales staff. ALSL did not

establish a written schedule for repayment of any of these

transferred funds (or interest thereon), and ALSL never demanded

that ALD repay any of the funds (or interest thereon). ALSL

never required that ALD pledge any of its assets to secure

repayment of any of the transferred funds, and ALD never pledged

any of its assets to secure such repayment. ALSL never required

that ALD’s members pledge security for repayment of any of the

transferred funds, and ALD’s members never pledged any such

security. ALD’s members never agreed to personally guarantee

The $43,418.06 payment that ALD made to ALSL on July 10,

1997, resulted from the reported liquidation of ALD’s assets in

VIII. Seasons of Sarasota

On October 24, 1994, William Shaner (Shaner) delivered

documentation to Seasons Management Co. (SMC) describing the -17-

Seasons of Sarasota project. Shaner later told HEI about the

possibility of investing in the project. Afterwards, in 1994,

Thomas retained an appraisal and consulting firm to prepare a

detailed analysis of the market for a retirement community in

Sarasota. The firm delivered such an analysis to Thomas on

December 23, 1994, in the form of a 39-page report (exclusive of

addenda) entitled “Analysis of Service Enhanced Retirement

Facility Market in Sarasota, Florida”. At the request of Thomas,

the firm on June 26, 1996, updated its analysis and conclusions

reflected in that report.

Eugene Schwartz (Schwartz) is unrelated by blood or marriage

to Thomas, Stethem, or any member of the Hubert family. In

January 1995, ALSL agreed to pay $3 million to Schwartz for 49.8

acres in Sarasota on which the Seasons of Sarasota was proposed

to be built. As a condition to the agreement, ALSL had to obtain

commitments from buyers of at least 59 condominium units which

were to be built on the land. Absent written notice to the

seller, ALSL had until December 31, 1995, to purchase the land

from Schwartz. Also in January 1995, SMC and ALD agreed that SMC

would direct the marketing of, manage, and operate the Seasons of

Sarasota. The duties and responsibilities of SMC were to begin

on January 1, 1995, and continue until December 31, 2004, unless

terminated earlier. -18-

The plan for the Seasons of Sarasota called for 298

individually owned condominium units with one to three bedrooms,

a 30,000-square-foot clubhouse, and an 80-unit assisted living

facility. Pursuant to the plan, construction of 98 condominium

units would start in the fall of 1996. The construction of the

Seasons of Sarasota was to be financed in phases with each phase

consisting of approximately one-third of the projected 298

condominium units.

On June 24, 1996, Provident Bank (Provident) relayed to

Thomas the possibility of Provident’s lending funds to ALD.

Provident would make the loan only if certain conditions were

met. One condition was that HEI be a comaker of the loan and

agree to certain financial covenants such as maintaining a stated

debt to equity ratio and a stated minimum net worth. A second

condition was that ALD procure in the first phase of construction

at least 45 firm contracts to purchase condominium units with a

total gross sale price of at least $10.8 million and total

initial earnest money deposits of at least $1.62 million. A

third condition was the monthly payment on the loan of accrued

interest and principal. A fourth condition was that the loan be

secured. A fifth condition was that the earnest money from sales

be deposited with Provident.

Through June 30, 1996, 34 condominium units in the Seasons

of Sarasota were reserved with refundable deposits. By the -19-

latter part of 1996, some individuals who had reserved

condominium units canceled their reservations, and the number of

cancellations exceeded the number of new reservations. By

December 31, 1996, ALD had not sold 45 of the condominium units

planned for the first phase.

ALD never purchased the land from Schwartz, and the

construction of the Seasons of Sarasota never began. Nor did

Provident ever lend any funds to ALD, ALSL, or HEI. On

December 31, 1996, the duties and responsibilities of SMC ended

when SMC and ALD agreed to terminate their agreement because the

land had not been purchased.

IX. LCL

LCL is a Wyoming limited liability company formed on

April 30, 1998. LCL filed its initial Federal partnership return

of income on the basis of a taxable year ended July 31, 1998

(LCL’s 1998 taxable year). LCL’s organizers were Thomas, in his

capacity as managing member of Hubert Commerce Center, Inc.

(HCC), and Ollinger, in his capacity as vice president of HBW.

HCC was connected with both the HEI and HHC affiliated groups.

LCL’s ownership consisted of 100 membership units. During

LCL’s 1998 taxable year, HBW received 99 of those units in

exchange for a $9,900 capital contribution, and HCC received the

last unit in exchange for a $100 capital contribution. On

April 30, 1998, HBW and LCL also executed as a contribution to -20-

LCL’s capital an assignment in which HBW transferred to LCL all

of HBW’s rights, title, and interest in its leases, subject to

existing loans.

Section 4.2 of LCL’s operating agreement stated that “No

Member shall be liable as such for the liabilities of the

Company.” On March 28, 2001, the LCL operating agreement was

amended and restated in its entirety (revised LCL operating

agreement), effective retroactively to January 1, 2000. The

revised LCL operating agreement is construed under Wyoming law,

and only the parties who signed the revised LCL operating

agreement (and their successors in interest) have any rights or

remedies under that agreement. The revised LCL operating

agreement stated that neither HBW nor HCC was required to make

any additional capital contribution to LCL. The revised LCL

operating agreement also stated:

7.7 Deficit Capital Account Restoration. If any Partner has a deficit Capital Account following the liquidation of his, her or its interest in the partnership, then he, she or it shall restore the amount of such deficit balance to the Partnership by the end of such taxable year or, if later, within 90 days after the date of such liquidation, for payment to creditors or distribution to Partners with positive capital account balances.

In 2000 and 2001, neither HBW nor HCC liquidated its

interest in LCL. Nor at those times did either member have a

deficit in its LCL capital account. -21-

X. Equipment Leasing Activities

A. 1991 Rapistan Conveyor System

Starwood Corp. (Starwood), Ministers Life--A Mutual Life

Insurance Co. (Ministers Life), Inter-Market Capital Corp.

(Inter-Market), and General Motors Corp. (GM) are corporations

unaffiliated with any Hubert company. Pursuant to agreements

dated April 30 and June 25, 1991, Starwood leased a 1991 Rapistan

conveyor system to GM. The term of that lease included the 180-

month period beginning November 1, 1991. For each of those 180

months, GM agreed to pay $13,659.83 on the first day of the

month, beginning November 1, 1991.

On October 1, 1991, Starwood purchased the 1991 Rapistan

conveyor system from Ministers Life for $1,327,237.89. All

payments on that purchase were to be made from proceeds from the

lease of the 1991 Rapistan conveyor system. The payment schedule

for the October 1, 1991, promissory note underlying the purchase

anticipated that the monthly payments would be $13,659.83,

starting November 1, 1991.

On October 31, 1991, Printgraphics purchased the 1991

Rapistan conveyor system (subject to the lease) from Starwood for

$1,412,468.68. On the same day, Printgraphics paid Starwood

$75,000 towards that purchase price and financed the rest by

assuming liability for the October 1, 1991, promissory note

between Starwood and Ministers Life. For each of its taxable -22-

years ended in 1992 through 1998, Printgraphics reported as to

the 1991 Rapistan conveyor system the following amounts of lease

income, interest expense, depreciation, and loss: 1992 1993 1994 1995 1996 1997 1998

Lease income $122,938 $163,918 $163,918 $163,918 $163,918 $163,918 $122,940 Interest expense (80,877) (117,907) (113,466) (108,596) (103,256) (97,401) (68,234) Depreciation (201,842) (345,913) (247,041) (176,417) (126,133) (125,992) (94,228) Loss 159,781 299,902 196,589 121,095 65,471 59,475 39,522

B. 1995 Computer Equipment

Capital Resources Group, Inc. (CRG), is a corporation

unaffiliated with any Hubert company. On April 30, 1995,

Starwood sold computer equipment (1995 computer equipment) to CRG

for $6,822,000, and CRG leased the 1995 computer equipment back

to Starwood. Pursuant to promissory notes dated April 30, 1995,

CRG promised to pay $445,538 and $6,058,983 to Starwood as to the

sale.

Also on April 30, 1995, Printgraphics purchased the 1995

computer equipment (subject to the lease) from CRG for

$6,822,000. Printgraphics paid CRG $360,000 and issued CRG a

short-term promissory note for $445,538 and an installment

promissory note for $6,016,462. The installment note stated it

was recourse to the extent of $2.2 million and that payments of

principal on the recourse portion would be reduced pro rata to

the extent the outstanding indebtedness on the note was reduced.

For each of its taxable years ended in 1995 through 1998,

Printgraphics reported as to the 1995 computer equipment the -23-

following amounts of lease income, interest expense,

depreciation, and income/(loss):

1995 1996 1997 1998

Lease income -0- $1,157,816 $1,646,796 $1,341,589 Interest expense ($150,412) (433,423) (490,523) (285,889) Depreciation (1,364,400) (2,183,040) (1,309,824) (589,467) Income/(loss) (1,514,812) (1,458,647) (153,551) 466,233

C. 1998 Amtel Equipment

Amtel Corp. (Amtel) and Third Street Services, Inc. (TSS),

are corporations that are unaffiliated with any Hubert company.

On April 30, 1998, CRG purchased from Starwood for $8,927,204.90

a 60.55-percent interest (60.55-percent interest) in certain

equipment (1998 Amtel equipment) leased by TSS to Amtel.

Pursuant to promissory notes dated April 30, 1998, CRG agreed to

pay Starwood $8,222,860.90 and $235,000. Also on April 30, 1998,

CRG leased the 60.55-percent interest back to Starwood for an

86-month term beginning August 1, 1998.

Also on April 30, 1998, LCL purchased the 60.55-percent

interest (subject to the lease) from CRG for $8,927,204.90.

Pursuant to promissory notes dated April 30, 1998, LCL agreed to

pay CRG $8,172,204.90 and $235,000. No individual member of LCL

signed or directly guaranteed these promissory notes, the first

of which stated it was recourse to the extent of $4.75 million

and that payments of principal and interest would be applied to

the recourse portion before the nonrecourse portion. The second

note stated it was nonrecourse. -24-

On July 31, 1998, CRG purchased from Starwood the remaining

39.45-percent interest (39.45-percent interest) in the 1998 Amtel

equipment for $5,814,720.10, and CRG leased the 39.45-percent

interest back to Starwood. Pursuant to promissory notes dated

July 31, 1998, CRG promised to pay Starwood $5,346,686.52 and

$53,932.54.

Also on July 31, 1998, LCL purchased the 39.45-percent

interest (subject to the lease) from CRG for $5,814,720.10.

Pursuant to promissory notes dated July 31, 1998, LCL promised to

pay CRG $5,310,887.56 and $53,832.54. No individual member of

LCL signed or guaranteed these notes, the first of which stated

it was recourse to the extent of $2.75 million and that payments

of principal and interest would be applied to the recourse

portion before the nonrecourse portion. The second note stated

it was nonrecourse.

For each of its taxable years ended in 1998 through 2001,

LCL reported as to the 1998 Amtel equipment the following amounts

of lease income, interest expense, depreciation, net “G&A”

expense and interest income, and loss:

1998 1999 2000 2001

Lease income -0- $1,987,157 2,167,807 $2,167,807 Interest expense ($156,167) (971,811) (877,785) (786,273) Depreciation (2,948,385) (4,717,416) (2,830,450) (1,698,270) Net G&A expense and interest income -0- 4,047 32,922 13,815 Loss 3,104,552 3,698,023 1,507,506 302,921 -25-

The portions of these losses allocated to HBW’s 99-percent

ownership interest were $3,073,507, $3,661,043, $1,492,431, and

$299,892, respectively.

D. 1999 Blisk Equipment

Relational Funding Corp. (RFC) is a corporation that is

unaffiliated with any Hubert company. On April 30, 1999, RFC

sold (subject to a lease) a Lear Precision ECM 1999 blisk machine

(1999 blisk equipment) to LCL for $2,950,382.86. At that time,

the 1999 blisk equipment was leased to General Electric Aircraft

Engines. LCL paid $133,000 towards the purchase, issued to RFC a

$30,742 short-term note, assumed a $403,505.60 long-term note of

RFC, and assumed RFC*s position with respect to lender liens on

the 1999 blisk equipment.

For each of its taxable years ended in 1999 through 2001,

LCL reported as to the 1999 blisk equipment the following amounts

of lease income, interest expense, depreciation, “G&A” expense

and interest income, and loss:

1999 2000 2001

Lease income $108,296 $433,185 $433,185 Interest expense (35,449) (172,353) (154,497) Depreciation (421,484) (722,543) (516,022) Net G&A expense and interest income 221 6,579 2,761 Loss 348,416 455,132 234,573

ownership interest were $344,932, $440,672, and $232,227,

respectively. -26-

E. 2000 Computer Equipment

On April 30, 2000, CRG purchased computer equipment (2000

computer equipment) from RFC for $765,326. Pursuant to

promissory notes dated April 30, 2000, CRG agreed to pay RFC

$56,850 and $672,101. On the same day, CRG leased the 2000

computer equipment back to RFC.

Also on April 30, 2000, LCL purchased the 2000 computer

equipment (subject to the lease) from CRG for $765,326, and LCL

executed promissory notes to CRG in the amounts of $56,850 and

$667,766. No individual member of LCL signed or directly

guaranteed the notes, the latter of which stated it was recourse

to the extent of $340,000 and that payments of principal would be

applied first to the recourse portion. For each of its taxable

years ended in 2000 and 2001, LCL reported as to the 2000

computer equipment the following amounts of lease income,

interest expense, depreciation, “G&A” expense and interest

income, and loss:

2000 2001

Lease income -0- $100,341 Interest expense ($17,065) (48,816) Depreciation (153,065) (244,904) Net G&A expense and interest income -0- 639 Loss 170,130 192,740

ownership interest were $168,429 and $190,813, respectively. -27-

F. 2000 RFC Equipment

RFC equipment) from RFC for $9,181,432 and leased the 2000 RFC

equipment back to RFC. Pursuant to promissory notes dated

April 30, 2000, CRG promised to pay RFC $663,400 and $8,080,320

as to the purchase.

Also on April 30, 2000, LCL purchased the 2000 RFC computer

equipment (subject to the lease) from CRG for $9,181,432.

Pursuant to promissory notes dated April 30, 2000, LCL promised

to pay CRG $663,400 and $8,029,222. No individual member of LCL

signed or directly guaranteed the notes, the latter of which

stated it was recourse to the extent of $3.225 million and that

payments of principal and interest would be applied first to the

recourse portion. For each of its taxable years ended in 2000

and 2001, LCL reported as to the 2000 RFC equipment the following

amounts of lease income, interest expense, depreciation, “G&A”

Lease Income -0- $1,545,155 Interest expense ($205,190) (508,995) Depreciation (1,836,287) (2,938,058) Net G&A expense and interest income -0- 9,848 Loss 2,041,477 1,892,050

ownership interest were $2,021,062 and $1,873,130 respectively. -28-

OPINION

I. Transferred Funds

A. Overview

Petitioners argue primarily that HEI’s transfers to ALSL

created debt which became uncollectible in HEI’s 1997 taxable

year, thus for that year entitling HEI to a bad debt deduction

under section 166.5 Alternatively, petitioners argue, the

transfers were HEI’s contribution to the capital of ALSL, which

entitled HEI for its 1997 taxable year to deduct an ordinary loss

resulting from a loss of that capital. Respondent argues that

the transfers were not debt. Respondent also argues that the

transfers were not capital contributions made by HEI, noting that

ALSL was owned not by HEI but primarily by the individuals who

controlled HEI.

We agree with respondent that HEI is not entitled to either

of its desired deductions with respect to the transfers. We

conclude that the transfers were not deductible for HEI’s 1997

taxable year as debt nor as contributions made by HEI to the

capital of ALSL.

5 Sec. 166(a)(1) provides that a taxpayer may deduct as an ordinary loss a debt which becomes worthless during the taxable year. -29-

B. Petitioners’ Claim to a Bad Debt Deduction

Petitioners bear the burden of proving that the transfers

are debt.6 See Rule 142(a)(1); Roth Steel Tube Co. v.

Commissioner, 800 F.2d 625, 630 (6th Cir. 1986), affg. T.C. Memo.

1985-58; Smith v. Commissioner, 370 F.2d 178, 180 (6th Cir.

1966), affg. T.C. Memo. 1964-278. Debt for Federal income tax

purposes connotes an existing, unconditional, and legally

enforceable obligation to repay. See Roth Steel Tube Co. v.

Commissioner, supra at 630; First Natl. Co. v. Commissioner,

289 F.2d 861, 864-865 (6th Cir. 1961), revg. and remanding

32 T.C. 798 (1959); Burrill v. Commissioner, 93 T.C. 643, 666

(1989); see also AMW Invs., Inc. v. Commissioner, T.C. Memo.

1996-235. Transfers between related parties are examined with

special scrutiny. Cf. Roth Steel Tube Co. v. Commissioner, supra

at 630. A transfer’s economic substance prevails over its form,

see Smith v. Commissioner, supra at 180; Byerlite Corp. v.

Williams, 286 F.2d 285, 291 (6th Cir. 1960), and a finding of

economic substance turns on whether the transfer would have

followed the same form had it been between the transferee and an

6 Petitioners have not raised the issue of sec. 7491(a), which shifts the burden of proof to the Commissioner in certain situations, and we conclude that sec. 7491(a) does not apply. In the case of a corporation such as each petitioner, sec. 7491(a)(2) limits the shifting of the burden of proof to situations where, among other things, the corporation shows that upon filing its petition in this Court, its net worth was no more than $7 million. See also 28 U.S.C. sec. 2412(d)(2)(B) (2000). Neither petitioner has made such a showing. -30-

independent lender, see Scriptomatic, Inc. v. United States,

555 F.2d 364 (3d Cir. 1977). The more a transfer appears to

result from an arm’s-length transaction, the more likely the

transfer will be considered debt. See Bayer Corp. v. Mascotech,

Inc. (In re Autosytle Plastics, Inc.), 269 F.3d 726, 750 (6th

Cir. 2001). The subjective intent of the parties to a transfer

that the transfer create debt does not override an objectively

indicated intent to the contrary. See Stinnett’s Pontiac Serv.,

Inc. v. Commissioner, 730 F.2d 634, 639 (11th Cir. 1984), affg.

T.C. Memo. 1982-314.

In the case of transfers from shareholders to their

corporations, courts generally refer to numerous factors to

determine whether the transfers create debt. Petitioners argue

that such an approach is irrelevant where, as here, a transfer is

made to a partnership rather than a corporation. Petitioners

assert that the Court in a case such as this must focus solely on

the form of the document connected with the transfer (here, the

ALSL note) and decide whether that document establishes a debtor-

creditor relationship under applicable State law. We disagree.

Petitioners have cited no authority to support their view, and we

believe that the relevant factors distinguishing debt from equity

are most helpful to us in deciding whether HEI transferred the

disputed funds to ALSL in an arm’s-length transaction made with a

genuine intention to create a debt. See Berthold v. -31-

Commissioner, 404 F.2d 119, 122 (6th Cir. 1968) (“Established

authority holds that the intention of the parties is the

controlling factor in determining whether or not advances should

be termed loans.”), affg. T.C. Memo. 1967-102; cf. Recklitis v.

Commissioner, 91 T.C. 874, 905 (1988).

The Court of Appeals for the Sixth Circuit, to which an

appeal of this case most likely lies, refers primarily to eleven

factors in distinguishing debt from equity. See Roth Steel Tube

Co. v. Commissioner, supra at 630. These factors are: (1) The

name given to an instrument underlying a transfer of funds;

(2) the presence or absence of a fixed maturity date and a

schedule of payments; (3) the presence or absence of a fixed

interest rate and actual interest payments; (4) the source of

repayment; (5) the adequacy or inadequacy of capitalization;

(6) the identity of interest between creditors and equity

holders; (7) the security for repayment; (8) the transferee’s

ability to obtain financing from outside lending institutions;

(9) the extent to which repayment was subordinated to the claims

of outside creditors; (10) the extent to which transferred funds

were used to acquire capital assets; and (11) the presence or

absence of a sinking fund to provide repayment. Id. No one

factor is controlling, and courts must consider the particular

circumstances of each case. Id. -32-

We turn to analyzing and weighing the relevant facts of this

case in the context of the 11 factors set forth in Roth Steel

Tube Co. v. Commissioner, supra.

1. Name of Certificate

We look to the name of the certificate evidencing a transfer

to determine whether the parties thereto intended that the

transfer create debt. Although the issuance of a note weighs

toward a finding of bona fide debt, see Bayer Corp. v. Mascotech,

Inc. (In re Autostyle Plastics, Inc.), supra at 750; Estate of

Mixon v. United States, 464 F.2d 394, 403 (5th Cir. 1972), the

mere fact that a taxpayer issues a note is not dispositive. The

issuance of a demand note is not indicative of genuine debt when

the note is unsecured, without a maturity date, and without

meaningful repayments. See Stinnett’s Pontiac Serv., Inc. v.

Commissioner, supra at 638; Tyler v. Tomlinson, 414 F.2d 844, 849

(8th Cir. 1969).

We give little weight to the fact that ALSL issued the ALSL

note to HEI. The ALSL note was a demand note with no fixed

maturity date, no written repayment schedule, no provision

requiring periodic payments of principal or interest, no

collateral, and no meaningful repayments. In addition, HEI never

made a demand for repayment or otherwise sought enforcement of

the ALSL note. See Stinnett’s Pontiac Serv., Inc. v.

Commissioner, supra at 640 (the fact that notes were due on -33-

demand but that the obligee never demanded payments supports a

strong inference that the obligee never intended to compel the

obligor to repay the notes). Although both HEI and ALSL posted

in their records that the transfers were loans, those postings

provide little if any support for a finding of bona fide debt.

Roth Steel Tube Co. v. Commissioner, 800 F.2d at 631 (citing

Raymond v. United States, 511 F.2d 185, 191 (6th Cir. 1975)).

Petitioners argue that HEI asserted its rights as a lender

by receiving all of the existing capital of ALSL upon its demise.

According to petitioners, had the transfers not been debt, then a

portion of that capital would have gone to Stethem and Thomas,

who together contributed $250,000 of capital to ALSL. We

consider this argument unpersuasive. We find nothing in the

record to support petitioners’ claim that HEI asserted its rights

as a lender by receiving all of the existing capital of ALSL upon

its claimed demise.7 We also find nothing in the record to

support petitioners’ claim that Stethem and Thomas failed to

receive anything of value as to their capital contributions.

Stethem and Thomas were fixtures in most of the financial

ventures of the Hubert family and their companies. In addition

7 Nor do we find that the business of either ALSL or ALD ceased in 1996 or 1997, as petitioners claim. Indeed, in and after December 1996, HEI made to ALSL nine transfers totaling $145,000, and ALSL made to ALD six transfers totaling $157,197.66. HEI also did not receive the reported liquidation proceeds until July 14, 1997. -34-

to serving with Thomas as a trustee of the HFT, Stethem was legal

counsel for the Hubert family and their companies and presumably

made a good living in that capacity. Thomas was HEI’s longtime

president and in that capacity received more than $800,000 in

compensation in just HEI’s 1997 and 1998 taxable years alone.

We also note that Thomas as of the time of trial continued to

work for the Hubert enterprise as its chief executive officer and

that his $200,000 contribution to ALSL’s capital was

contemporaneous with his receipt from HEI of an amount of officer

compensation that appears to have been inflated to enable him to

make that contribution.

This factor weighs toward a finding that the transfers did

not create bona fide debt.

2. Fixed Maturity Date and Schedule of Payments

The absence of a fixed maturity date and a fixed obligation

to repay weighs against a finding of bona fide debt. See Bayer

Corp. v. Mascotech, Inc. (In re Autostyle Plastics, Inc.), 269

F.3d at 750; Roth Steel Tube Co. v. Commissioner, supra at 631.

The ALSL note had no fixed maturity date. While petitioners

assert that the ALSL note was a demand note for which payment

could have been requested at any time, the fact of the matter is

that HEI never made any such demand and, more importantly, ALSL

never had the ability to honor such a request had one been made.

ALSL made its first (and only) payment on the ALSL note -35-

approximately 2-1/2 years after HEI’s first transfer to ALSL and

did so only on account of ALD’s claimed liquidation. Moreover,

notwithstanding this lack of repayments throughout the referenced

2-1/2-year period, HEI continued to transfer funds to ALSL

without any schedule for repayment. HEI even transferred a total

of $95,000 to ALSL in 1997 even though in December 1996 HEI

decided to stop funding the Seasons of Sarasota project and ALSL

treated the “debt” as discharged on its Federal income tax return

for 1996.

Petitioners ask the Court to conclude that the issuance of

the ALSL note as a demand note strongly supports a finding of

debt because the obligeee of a demand note, unlike an equity

holder, may at any time demand repayment. We decline to reach

such a conclusion. As noted by the Court of Appeals for the

Eleventh Circuit, “an unsecured note due on demand with no

specific maturity date, and no payments is insufficient to

evidence a genuine debt.” Stinnett’s Pontiac Serv., Inc. v.

Commissioner, 730 F.2d at 638; cf. Bayer Corp. v. Mascotech, Inc.

(In re Autostyle Plastics, Inc.), supra at 750 (“use of demand

notes along with a fixed rate of interest and interest payments

is more indicative of debt than equity” (Emphasis added.)).

Repayment of the ALSL note was unsecured, HEI never prepared a

written repayment schedule as to the transfers, and ALSL never

had assets available to pay all, or even a significant part, of -36-

the ALSL note. Whether or when to make demand for repayment of

the transfers was within the discretion of HEI and was not

conditioned upon the occurrence of any stated event. See

Stinnett’s Pontiac Serv., Inc. v. Commissioner, supra at 639.

3. Interest Rate and Actual Interest Payments

A reasonable lender is concerned about receiving payments of

interest as compensation for, and commensurate with, the risk

assumed in making the loan. See id. at 640; cf. Deputy v. du

Pont, 308 U.S. 488, 498 (1940) (in the business world, interest

is paid on debt as “compensation for the use or forbearance of

money”). The absence of an adequate rate of interest and actual

interest payments weighs strongly against a finding of bona fide

debt. See Bayer Corp. v. Mascotech, Inc. (In re Autostyle

Plastics, Inc.), supra at 750; Roth Steel Tube Co. v.

Commissioner, supra at 631.

Although the ALSL note on its face bore a rate of interest,

the facts of this case persuade us that the parties to the note

did not intend that ALSL actually pay HEI any (let alone a market

rate of) interest for the use of the transferred funds unless the

Seasons of Sarasota project was successful. We do not believe

that a reasonable lender would have lent unsecured funds to ALSL,

a company with no revenues and few liquid assets, at the rate of -37-

interest stated in the ALSL note. A transferor of funds who does

not insist on reasonable interest payments as to the use of the

funds may not be a bona fide lender. See Stinnett’s Pontiac

Serv., Inc. v. Commissioner, supra at 640.

ALSL never paid any interest to HEI as to the transferred

funds and made but a single, nominal payment as to the principal

of those funds. Petitioners assert that payments were not made

because neither principal nor interest was ever due under the

terms of the ALSL note. We consider this assertion unavailing.

Indeed, HEI did not even report that accrued interest was owing

on the ALSL note until more than 18 months after the first

transfer of funds.

4. Source of Repayment

Repayment that depends solely upon the success of the

transferee’s business weighs against a finding of bona fide debt.

Repayment that does not depend on earnings weighs toward a

finding of debt. See Bayer Corp. v. Mascotech, Inc. (In re

Autostyle Plastics, Inc.), supra at 751; Roth Steel Tube Co. v.

Commissioner 800 F.2d at 632; Lane v. United States, 742 F.2d

1311, 1314 (11th Cir. 1984). “An expectation of repayment solely

from * * * earnings is not indicative of bona fide debt

regardless of its reasonableness.” Roth Steel Tube Co. v. -38-

Commissioner, supra at 631 (citing Lane v. United States, supra

at 1314); see also Stinnett’s Pontiac Serv., Inc. v.

Commissioner, supra at 638-639; Raymond v. United States,

511 F.2d at 191; Segel v. Commissioner, 89 T.C. 816, 830 (1987);

Deja Vu, Inc. v. Commissioner, T.C. Memo. 1996-234.

HEI’s transfers to ALSL were placed at the risk of ALSL’s

business. ALSL’s ability to repay these transfers depended

primarily (if not solely) on its earnings, which in turn rested

on the success of ALD and the Seasons of Sarasota project. ALSL

was unable to repay the ALSL note as ALSL had no revenue and

virtually no liquid assets.

5. Capitalization

Thin or inadequate capitalization to fund a transferee’s

obligations weighs against a finding of bona fide debt. See Roth

Steel Tube Co. v. Commissioner, supra at 630; Stinnett’s Pontiac

Serv., Inc. v. Commissioner, supra at 639.

The record indicates that ALSL was inadequately capitalized

to be, as it was, the funding vehicle for ALD and that ALSL had

no meaningful capital, apart from the transferred funds, either

before or when it received the transferred funds. While ALSL

received capital contributions totaling $250,000 from Thomas and

Stethem, that amount was small in comparison to the amount of the -39-

transferred funds and minuscule in comparison to the cost of the

Seasons of Sarasota project. As to that project, ALD agreed to

pay $3 million for land and had agreed to pay construction-

related costs potentially totaling millions of dollars more. For

its own equity capitalization, ALD had only $100,000 from its

limited partner Culpepper.

6. Identity of Interest

Transfers made in proportion to ownership interests weigh

against a finding of bona fide debt. A sharply disproportionate

ratio between an ownership interest and the debt owing to the

transferor by the transferee generally weighs toward a finding of

Plastics, Inc.), 269 F.3d at 751; Stinnett’s Pontiac Serv., Inc.

v. Commissioner, 730 F.2d at 630; Estate of Mixon v. United

States, 464 F.2d at 409.

HEI was not an owner of ALSL. HFT’s controlling settlors

and trustees were. In fact, the only portion of ALSL not owned

by those individuals was the 5-percent interest owned by

Ollinger, an HEI vice president, who never made any contribution

of capital to ALSL in return for his interest. The individuals

who controlled HEI effectively caused HEI to fund their

investment in ALSL. -40-

This factor is either inapplicable or does not support a

finding that the transfers created bona fide debt.

7. Presence or Absence of Security

The absence of security for the repayment of transferred

funds weighs strongly against a finding of bona fide debt. See

Bayer Corp. v. Mascotech, Inc. (In re Autostyle Plastics, Inc.),

supra at 752; Roth Steel Tube Co. v. Commissioner, supra at 632;

Lane v. United States, supra at 1317; Raymond v. United States,

supra at 191; Austin Village, Inc. v. United States, 432 F.2d

741, 745 (6th Cir. 1970).

The disputed transfers were unsecured.

8. Inability To Obtain Comparable Financing

The question of whether a transferee could have obtained

comparable financing from an independent source is relevant in

measuring the economic reality of a transfer. See Roth Steel

Tube Co. v. Commissioner, supra at 631; Estate of Mixon v. United

States, supra at 410; Nassau Lens Co. v. Commissioner, 308 F.2d

39, 47 (2d Cir. 1962), remanding 35 T.C. 268 (1960). Evidence

that a transferee could not at the time of the transfer obtain a

comparable loan from an arm’s-length creditor weighs against a

finding of bona fide debt. See Roth Steel Tube Co. v.

Commissioner, supra at 631; Stinnett’s Pontiac Serv., Inc. v. -41-

Commissioner, supra at 640; Calumet Indus., Inc. v. Commissioner,

95 T.C. 257, 287 (1990).

We do not believe that a creditor dealing at arm’s length

would have made the transfers to ALSL under the terms that

petitioners allege were entered into between ALSL and HEI. In

fact, ALD discussed borrowing funds from a commercial lender;

i.e., Provident. Although Provident did not lend any funds to

ALD, the terms of the proposed financing arrangement were

different in many regards from those contained in the ALSL note.

First, Provident would have required that HEI be a co-maker of

the note. Second, Provident would have required that HEI agree

to certain financial covenants such as the maintenance of a

stated debt to equity ratio and a stated minimum net worth.

Third, Provident would have required the borrower to provide

security, collateral, and earnest money and to pay accrued

interest and principal monthly. Fourth, Provident would have

required that ALD have in the first phase of construction at

least 45 firm contracts to purchase condominium units with a

initial earnest money deposits of at least $1.62 million. Fifth,

Provident would have required that any earnest money from the

sales be deposited with Provident. None of these requirements,

or anything like them, was contained in the financing arrangement

between ALSL and HEI. -42-

9. Subordination

Subordination of purported debt to the claims of other

creditors weighs against a finding of bona fide debt. See Roth

Steel Tube Co. v. Commissioner, 800 F.2d at 631-632; Stinnett’s

Pontiac Serv., Inc. v. Commissioner, supra at 639; Raymond v.

United States, 511 F.2d at 191; Austin Village, Inc. v. United

States, supra at 745.

ALSL has never had any creditors. Given that the transfers

were unsecured, however, their right to repayment would have been

subordinate to the interests of any secured creditors.

10. Use of Funds

A transfer of funds to meet the transferee’s daily business

needs weighs toward a finding of debt. A transfer of funds to

purchase capital assets weighs against a finding of bona fide

debt. See Roth Steel Tube Co. v. Commissioner, supra at 632;

Stinnett’s Pontiac Serv., Inc. v. Commissioner, supra at 640;

Raymond v. United States, supra at 191.

The transfers were not used to pay ALSL’s daily operating

expenses because ALSL had no operating expenses. Although the

transfers also were not used to acquire tangible capital assets, -43-

the transfers were used by ALSL in a similar sense in that they

were retransferred to ALD to use on the Seasons of Sarasota

project. But for the transfers of the funds from HEI to ALSL,

ALSL would not have been able to make most of the transfers to

ALD.

11. Presence or Absence of a Sinking Fund

The failure to establish a sinking fund for repayment weighs

against a finding of bona fide debt. See Bayer Corp. v.

Mascotech, Inc. (In re Autostyle Plastics, Inc.), 269 F.3d at

753; Roth Steel Tube Co. v. Commissioner, supra at 632; Lane v.

United States, 742 F.2d at 1317; Raymond v. United States, supra

at 191; Austin Village, Inc. v. United States, supra at 745.

ALSL did not establish a sinking fund for repayment of the

ALSL note. While petitioners invite this Court to disregard this

factor, asserting that the Court of Appeals for the Sixth Circuit

“is out of touch with economic reality” in relying upon this

factor, we decline to do so. As is true with respect to all of

these factors, this factor is not controlling in and of itself

but is merely one factor that we consider in determining the

objectively indicated intent of ALSL and HEI as to the

characterization of the transferred funds. -44-

12. Conclusion

On the basis of our review of the entire record, we find it

extremely improbable that an arm’s-length lender at the time of

the transfers would have lent unsecured, at a low rate of

interest, and for an unspecified period of time to an entity in

ALSL’s questionable financial condition. Security, adequately

stated interest, and repayment arrangements (or efforts to secure

the same) are important proofs of intent, and here such proofs

are notably lacking. Economic realities require that HEI’s

transfers be characterized as capital contributions for Federal

income tax purposes, and we so hold. Thus, we also hold that HEI

is not entitled to any bad debt deduction with respect to the

transfers.

C. Petitioners’ Claim to a Deduction for a Loss of Capital

Petitioners argue alternatively that HEI may deduct the

transfers as a loss on an abandonment of its equity interest in

ALSL. We disagree. We are unable to find in the record that HEI

had any equity interest in ALSL, let alone any such interest that

it may deduct as a loss.

HEI and its owners and advisers were experienced in many

lines of business conducted in many ways. In structuring its

involvement in the Seasons of Sarasota project, HEI chose not to -45-

become an owner of ALSL and never became such an owner. ALSL’s

owners, on the other hand, who were themselves indirect owners

and insiders of HEI, did choose to become ALSL’s owners. They

did this not by using their personal funds to pay for their

equity but by using HEI’s funds. Distributions by a corporation

are treated as dividends to a shareholder (to the extent of the

corporation’s earnings and profits, see Estate of DeNiro v.

Commissioner, 746 F.2d 327, 332 (6th Cir. 1984)) if the

distributions are made for the shareholder’s personal benefit

without any expectation of repayment. See Hagaman v.

Commissioner, 958 F.2d 684, 690-691 (6th Cir. 1992), affg. and

remanding T.C. Memo. 1987-549; J.F. Stevenhagen Co. v.

Commissioner, T.C. Memo. 1975-198, affd. 551 F.2d 106 (6th Cir.

1977); see also Shedd v. Commissioner, T.C. Memo. 2000-292; Davis

v. Commissioner, T.C. Memo. 1995-283. Such is so even if the

funds are not distributed directly to the shareholder. See Rapid

Elec. Co. v. Commissioner, 61 T.C. 232, 239 (1973); see also J.F.

Stevenhagen Co. v. Commissioner, supra.

HEI had no equity in ALSL, and HEI’s transfers of the funds

to ALSL enhanced the controlling settlors’ investments in ALSL;

e.g., the controlling settlors never made any capital

contributions to ALSL from their personal funds but still

received interests in ALSL totaling 60 percent. The transfers

also were made without a reasonable expectation of repayment. -46-

Instead, we find in the record that the primary purpose of HEI’s

transfers to ALSL, an entity controlled by the same individuals

who controlled HEI, was to benefit those individuals, see Sammons

v. Commissioner, 472 F.2d 449, 451, 456 (5th Cir. 1972), affg. in

part, revg. in part on another ground T.C. Memo. 1971-145; Wilkof

v. Commissioner, T.C. Memo. 1978-496, affd. 636 F.2d 1139 (6th

Cir. 1981); McLemore v. Commissioner, T.C. Memo. 1973-59, affd.

494 F.2d 1350 (6th Cir. 1974), and was without regard to any

business purpose or benefit to HEI.8

II. Losses From Equipment Leasing Activities

During the relevant years, petitioners were connected with

the following leasing activities: (1) In 1991, Printographics

began the activity concerning the 1991 Rapistan conveyor system;

(2) in 1995, Printographics began the activity concerning the

1995 computer system; (3) in 1998, LCL began the activities

concerning the 1998 Amtel equipment; (4) in 1999, LCL began the

activity concerning the 1999 blisk equipment; (5) in 2000, LCL

began the activities concerning the 2000 computer equipment and

the 2000 RFC equipment.

8 We need not and do not decide whether the transfers were in fact dividends to HEI’s nonparty shareholder. For even if they were not, HEI could not deduct the outlay made primarily for the benefit of its shareholder rather than for a business or investment purpose of its own. See Hood v. Commissioner, 115 T.C. 172, 179 (2000). -47-

B. Aggregation

Petitioners argue that section 465(c)(2)(B)(i) allows LCL to

aggregate its 1998, 1999, and 2000 activities into a single

activity for purposes of the at-risk rules of section 465. (The

relevant provisions of section 465(c) are set forth in an

appendix to this Opinion.) Petitioners argue that section

1.465-1T, Temporary Income Tax Regs., 50 Fed. Reg. 6014 (Mar. 11,

1985), interprets section 465(c)(2)(B)(i) to the contrary and

assert that these regulations are invalid as inconsistent with

the statute. Respondent argues that the referenced regulations

preclude LCL from aggregating one year’s leasing activities with

another year’s leasing activities and asserts that the referenced

regulations are consistent with section 465(c)(2)(B)(i). We

agree with respondent that section 465(c)(2)(B)(i) does not allow

for the aggregation desired by petitioners. Because we do not

read the referenced regulations to address the issue at hand, we

do not discuss them further.

Section 465(c)(2)(A)(ii) generally provides that a taxpayer

may not aggregate its equipment leasing activities for purposes

of the at-risk rules. An exception is found, however, in the

case of partnerships and S corporations. Under this exception,

all activities of a partnership or S corporation with respect to

section 1245 properties are considered to be a single activity to

the extent that the “properties are leased or held for lease, and -48-

* * * are placed in service in any taxable year of the

partnership or S corporation”. Sec. 465(c)(2)(B)(i).

Petitioners read the quoted text, with a focus especially on

the word “any”, to mean that all of LCL’s equipment leasing

activities are viewed as a single activity, notwithstanding the

fact that all of the activities did not arise in the same taxable

year. We read that text differently. While petitioners focus

primarily on the single word “any” to support their

interpretation, the word “any” may not be construed in isolation

but must be construed in the context of the statute as a whole.

See Small v. United States, U.S. , 125 S. Ct. 1752 (2005);

United States v. Alvarez-Sanchez, 511 U.S. 350, 357 (1994).

Statutes should be interpreted as a whole to give effect to every

clause, sentence, and word therein, see Market Co. v. Hoffman,

101 U.S. 112, 115 (1879), and the duty of a court is to render

that type of interpretation whenever possible, cf. United States

v. Menasche, 348 U.S. 528, 538-539 (1955); Montclair v. Ramsdell,

107 U.S. 147, 152 (1883). Such an approach is a “cardinal

principle of statutory construction”. Williams v. Taylor,

529 U.S. 362, 404 (2000).

In accordance with that approach, we apply the plain meaning

of the words set forth in section 465(c)(2)(B), see Venture

Funding, Ltd. v. Commissioner, 110 T.C. 236, 241-242 (1998),

affd. without published opinion 198 F.3d 248 (6th Cir. 1999), and -49-

we do so mindful of the statute as a whole. We conclude that

Congress’s use of the word “any” denotes one (i.e., the same)

taxable year and that LCL’s aggregated activities are only those

activities that relate to leased personal property placed in

service in the same taxable year.9 As we understand petitioners’

contrary interpretation, its effect would be that virtually “all

activities [of a partnership or S corporation] with respect to

section 1245 properties which * * * are leased or held for lease

* * * shall be treated as a single activity.” Petitioners do not

explain how that interpretation does not render section

465(c)(2)(B)(i)(II) surplusage, and we are unable to give such an

explanation either. Nor do petitioners explain how their

interpretation harmonizes with section 465(c)(2)(B)(ii) and, more

particularly, the reference in that section to section

465(c)(3)(B). Under petitioners’ interpretation, section

465(c)(2)(B)(ii) also would be surplusage in that all equipment

leasing activities of a partnership or S corporation would

already be considered to be a single activity under section

465(c)(2)(B)(i).

Petitioners’ reliance on the word “any” to reach their

interpretation also is misplaced. The word “any” denotes “One,

some, every, or all without specification”, The American Heritage

9 By cross-reference from sec. 465(c)(1)(C), sec. 1245(a) provides that the term “section 1245 property” as used in sec. 465 includes personal property. -50-

Dictionary of the English Language 81 (4th ed. 2000), and

Congress’s use of the word “any” “can and does mean different

things depending upon the setting”, Nixon v. Mo. Municipal

League, 541 U.S. 125, 132 (2004). In this setting, we simply do

not understand Congress’s use of that word to establish its

intent that section 465(c)(2)(B)(i) allow LCL to treat all of its

equipment leasing activities as a single activity regardless of

the year in which the equipment was placed in service. The fact

that Congress prescribed in the statute the singular form of the

word “year” adds to our belief.

While the legislative history underlying the enactment of

section 465(c)(2)(B) as applied to section 1245 properties is

sparse and of little benefit to our inquiry, see H. Conf. Rept.

98-861, at 1122 (1984), 1984-3 C.B. (Vol.2) 1, 376, we believe

that the setting surrounding the enactment of section

465(c)(2)(B) also is consistent with our conclusion. Section

465(c)(2) was enacted as part of the Deficit Reduction Act of

1984 (DEFRA), Pub. L. 98-369, sec. 432(b), 98 Stat. 814, which

changed the aggregation rules for partnerships and S corporations

with respect to equipment leasing activities (as well as the

other activities listed in section 465(c)(1)) for taxable years

beginning after December 31, 1983. Before DEFRA, partnerships

and S corporations aggregated all activities within each of five

specified categories for purposes of section 465. Thus, a -51-

partnership or S corporation could aggregate all of its leased

section 1245 property, while other taxpayers treated each of

their properties in that category as a separate activity. As

amended by DEFRA, section 465(c)(2) generally requires, except as

provided in section 465(c)(2)(B), that partnerships and S

corporations separate equipment leasing activities (and the other

activities listed in section 465(c)(1)) on a property-by-property

basis, as do other taxpayers. If petitioners’ interpretation

were adopted, permitting all leased section 1245 properties of a

partnership or S corporation to be aggregated into one activity

for purposes of the at-risk rules, section 465(c)(2), as amended

by DEFRA, would largely be ineffective.

We conclude by noting that our interpretation of section

465(c)(2)(B)(i) to refer to a single taxable year rather than all

of a taxpayer’s taxable years coincides with the views of

commentators. Since the enactment of section 465(c)(2)(B),

commentators have consistently agreed with the interpretation

that we espouse today. See, e.g., Starczewski, 550-2nd Tax

Management Portfolio (BNA), "At-Risk Rules" A-18 n.153 (“For the

leasing of § 1245 property that is all placed in service in a

single taxable year, § 465(c)(2)(B)(i) specifically provides for

aggregation.”) & A-19 (“The partnership aggregation rule

apparently does not apply to a partnership or S corporation that

leases equipment that is placed in service in different years.”) -52-

(2003); McGovern, “Liabilities of the Firm, Member Guaranties,

and the At Risk Rules: Some Practical and Policy Considerations”,

7 J. Small & Emerging Bus. L. 63, 81 (Spring 2003) (“Section 465

[more specifically identified in a footnote as section

465(c)(2)(B)] provides that if equipment leasing is carried on by

a partnership or subchapter S corporation, all items of equipment

that are placed in service during the same taxable year are

treated as constituting a single activity.”); Pennell, “Separate

Treatment of At-Risk Activities Under Section 465 Delayed”, 62 J.

Taxn. 372 (1985) (“For that category [section 1245 property],

aggregation based on the taxable year the properties were placed

in service is allowed under the special rule in Section

465(c)(2)(B).”). We have not found (nor have petitioners cited)

any treatise or article that sets forth a contrary

interpretation.

C. At-Risk Amounts

Petitioners argue that the deficit capital account

restoration provision in the revised LCL operating agreement

exposed LCL’s members to liability for their respective shares of

LCL’s recourse debt. Respondent argues that this provision was

not operative during the relevant years because it required that

an LCL member first liquidate its interest in LCL, an event that

never occurred during the relevant years. Respondent argues

alternatively that the provision, if operative, did not make the -53-

members liable for LCL’s recourse obligations in that a third

party lender did not under the revised LCL operating agreement

have the right to force the members to abide by any obligation

that LCL failed to honor. We agree with respondent that LCL’s

members were not at risk for any of the disputed amounts.

Congress enacted section 465 to limit the use of artificial

losses created by deductions from certain leveraged investment

activities. Such losses may be used only to the extent the

taxpayer is at risk economically. Generally, the amount at risk

includes (1) the amount of money and the adjusted basis of

property contributed to the activity by the taxpayer and

(2) borrowed amounts for which the taxpayer is personally liable.

Sec. 465(b).

The aspect of petitioners’ dispute with respondent’s

application of the at-risk rules rests on whether LCL’s members

may take into account any part of LCL’s recourse obligations. We

agree with respondent that they may not. The recourse notes

signed by LCL were not personally guaranteed by LCL’s members,

and applicable State (Wyoming) law provides that the members of a

limited liability company are not personally liable for the

debts, obligations, or liabilities of the company. See Wyo.

Stat. Ann. sec. 17-15-113 (LexisNexis 2005). The agreements of

LCL also contain no provisions obligating its members to pay

LCL’s debts, obligations, or expenses. Because LCL’s members did -54-

not assume personal liability for the notes, the members are not

at risk under section 465(b)(1)(B) and (2)(A) with respect to

LCL’s recourse obligations. Cf. Emershaw v. Commissioner,

949 F.2d 841 (6th Cir. 1991), affg. T.C. Memo. 1990-246.

Petitioners seek a contrary result, focusing on the deficit

capital account restoration provision in section 7.7 of the

revised LCL operating agreement. Petitioners argue that this

provision made LCL’s members personally liable for LCL’s recourse

obligations for purposes of applying the at-risk rules. We

disagree. As observed by respondent, section 7.7 contains a

condition that must be met before the deficit capital account

restoration obligation arises. In accordance with that

condition, an LCL member must first liquidate its interest in LCL

before the member has any obligation to the entity. Neither HBW

nor HCC liquidated its interest in LCL during the relevant years.

III. Conclusion

We sustain respondent’s determinations. We have considered

all of petitioners’ arguments for holdings contrary to those set

forth in this Opinion and have rejected those arguments not

discussed herein as meritless. We have considered respondent’s

arguments only to the extent discussed herein.

Decisions will be entered

for respondent. -55-

APPENDIX

SEC. 465(c). Activities to Which Section Applies.--

(1) Types of activities.--This section applies to any taxpayer engaged in the activity of--

(A) holding, producing, or distributing motion picture films or video tapes,

(B) farming (as defined in section 464(e)),

(C) leasing any section 1245 property (as defined in section 1245(a)(3)),

(D) exploring for, or exploiting, oil and gas resources or

(E) exploring for, or exploiting, geothermal deposits (as defined in section 613(e)(2))

as a trade or business or for the production of income.

(2) Separate activities.--For purposes of this section--

(A) In general.--Except as provided in subparagraph (B), a taxpayer's activity with respect to each--

(i) film or video tape,

(ii) section 1245 property which is leased or held for leasing,

(iii) farm,

(iv) oil and gas property (as defined under section 614), or

(v) geothermal property (as defined under section 614),

shall be treated as a separate activity. -56-

(B) Aggregation rules.--

(i) Special rule for leases of section 1245 property by partnerships or S corporations.--In the case of any partnership or S corporation, all activities with respect to section 1245 properties which--

(I) are leased or held for lease, and

(II) are placed in service in any taxable year of the partnership or S corporation,

shall be treated as a single activity.

(ii) Other aggregation rules.--Rules similar to the rules of subparagraphs (B) and (C) of paragraph (3) shall apply for purposes of this paragraph.

(3) Extension to other activities.--

(A) In general.--In the case of taxable years beginning after December 31, 1978, this section also applies to each activity--

(i) engaged in by the taxpayer in carrying on a trade or business or for the production of income, and

(ii) which is not described in paragraph (1).

(B) Aggregation of activities where taxpayer actively participates in management of trade or business.--Except as provided in subparagraph (C), for purposes of this section, activities described in subparagraph (A) which constitute a trade or business shall be treated as one activity if -- -57-

(i) the taxpayer actively participates in the management of such trade or business, or

(ii) such trade or business is carried on by a partnership or an S corporation and 65 percent or more of the losses for the taxable year is allocable to persons who actively participate in the management of the trade or business.

(C) Aggregation or separation of activities under regulations.--the secretary shall prescribe regulations under which activities described in subparagraph (A) shall be aggregated or treated as separate activities.