Louis P. Smaldino

CourtUnited States Tax Court
DecidedNovember 10, 2021
Docket5437-18
StatusUnpublished

This text of Louis P. Smaldino (Louis P. Smaldino) is published on Counsel Stack Legal Research, covering United States Tax Court primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Louis P. Smaldino, (tax 2021).

Opinion

T.C. Memo. 2021-127

UNITED STATES TAX COURT

LOUIS P. SMALDINO, Petitioner v. COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket No. 5437-18. Filed November 10, 2021.

Lavonne D. Lawson and Charles W. Morris, for petitioner.

Jenny R. Casey, Emerald G. Smith, and Kim-Khanh Nguyen, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

THORNTON, Judge: Petitioner owned and operated numerous rental

properties in southern California. He placed 10 of these properties in Smaldino

Investments, LLC (LLC), which he owned through a revocable trust. In 2013 he

transferred about 8% of the LLC class B member interests to the Smaldino 2012

Dynasty Trust (Dynasty Trust), an irrevocable trust that he had created a few

Served 11/10/21 -2-

[*2] months earlier for the benefit of his children and grandchildren. Around the

same time, petitioner purportedly transferred about 41% of the LLC class B

member interests to his wife, Agustina Smaldino, who purportedly retransferred

them to the Dynasty Trust the next day.

On petitioner’s 2013 gift tax return, he reported as a taxable gift only the

approximately 8% of the LLC class B membership interests he had transferred

directly to the Dynasty Trust. Respondent determined that petitioner had made a

taxable gift to the Dynasty Trust of 49% of the class B membership interests,

including the approximately 41% interest that assertedly had passed from

petitioner to the Dynasty Trust indirectly through Mrs. Smaldino. After revaluing

the LLC interests, respondent determined that petitioner had a $1,154,000 gift tax

deficiency for 2013.

The issues for decision are: (1) the proper characterization for gift tax

purposes of petitioner’s purported transfer of LLC class B member interests to

Mrs. Smaldino followed by her purported retransfer of these same interests to the

Dynasty Trust and (2) the fair market value of the LLC class B member interests

that petitioner transferred, directly or indirectly, to the Dynasty Trust. -3-

[*3] FINDINGS OF FACT1

The parties have stipulated some facts. We incorporate by this reference the

parties’ stipulation of facts and the attached exhibits. When he timely petitioned

this Court, petitioner resided in California.

Petitioner’s Background and Estate Planning

After practicing for a time as a certified public accountant and serving as the

treasurer of a computer company, petitioner purchased his father’s liquor store

business, which he then operated for over 35 years. He eventually expanded his

business holdings to include apartment buildings, which he managed as a sole

proprietor. By 2008 he had sold all his liquor stores, and his only remaining

business was owning and managing what ultimately became an $80 million

portfolio of real estate.

Petitioner has been married to Mrs. Smaldino since 2006. She has a

master’s degree in economics and since about 1995 has worked almost

continuously in petitioner’s businesses--first in his liquor-store business and, after

a three-year interval, in his property-management business.

1 Unless otherwise indicated, all section references are to the Internal Revenue Code (Code) in effect at all relevant times, and all Rule references are to the Tax Court Rules of Practice and Procedure. -4-

[*4] Petitioner has 6 children from a prior marriage and 10 grandchildren. Two

of the children work in petitioner’s property-management business.

In 2012, when he was 69, a health scare motivated petitioner to get his estate

planning in order. He and Mrs. Smaldino agreed that she should have security in

her own assets; they did not want her assets and his children’s assets commingled

as part of the estate plan. Petitioner wanted to pass his business to his children and

grandchildren and to give many of his remaining assets to Mrs. Smaldino.

Similarly, she wanted petitioner’s progeny to have the property-management

business.

Petitioner and Mrs. Smaldino developed a plan to provide his progeny a

bundle of assets comprising certain properties in the property-management

company and to provide her a separate group of assets that would far exceed any

share that the children received. As explained below, this plan involved placing

certain of petitioner’s business properties in the LLC and then transferring interests

in the LLC to a trust for the benefit of his children and grandchildren. Petitioner

resolved to transfer up to 50% of the LLC interests, the maximum he could transfer

without triggering reassessment of property taxes on the LLC’s assets. -5-

[*5] Smaldino Investments, LLC

Petitioner created the LLC in 2003, but it remained inactive until late 2012,

when he transferred 10 of his real estate holdings to it. As trustee of the Smaldino

Family Trust (a revocable trust that petitioner had created on the same day in 2003

as the LLC), he held all the ownership interests in the LLC and served as its

manager.

The LLC’s operating agreement distinguishes a “Member” from an

“Assignee”. A “Member” has both an economic interest in the LLC and the right

to participate in the LLC’s affairs. By contrast, the operating agreement defines an

“Assignee” as a person who is assigned all or part of a member’s economic interest

but who lacks other rights accorded to members, such as the right to vote or

participate in management or the right to obtain information about the LLC’s

business and affairs. The operating agreement expressly states: “‘Member’ as

defined herein does not include an Assignee.” It further states:

11.5 Transfer and Assignment of Membership Interests. No Member shall be entitled to transfer, assign, convey, sell, encumber or in any way alienate all or any part of such Member’s Membership Interest, and no Assignee shall be admitted as a substituted Member, except as expressly provided for in Section 11.5(c) herein.

* * * * * * *

(b) Substitution of Members. An Assignee of a Membership Interest shall have the right to become a substituted Member only if -6-

[*6] (i) the requirements of this Section 11.5 are met, (ii) such Assignee executes an instrument satisfactory to the Board accepting and adopting the terms and provisions of this Operating Agreement, and (iii) such person pays any reasonable expenses in connection with such substituted Member’s admission as a new Member. The admission of an Assignee as a substituted Member shall not result in the release of the Member who assigned the Membership Interest from any liability that such Member may have to the Company.

(c) Permitted Transfers. Subject to the provisions of Subparagraph 11.5(f)(iii), the Membership Interest of any Member may be transferred, and the Assignee thereof shall be admitted as a substituted Member, without the prior Written consent of the Board to: (i) any other Member or (ii) a revocable or irrevocable trust for the benefit of the Member or the Member’s children, grandchildren or other family members who are descendents [sic] of Louis P. Smaldino (or, where the Member is a trust, a revocable or irrevocable trust for the benefit of any beneficiary of the Member’s trust who is otherwise a permitted transferee).

(f) No Effect to Transfers in Violation of Agreement. Upon any transfer of a Membership Interest in violation of this Section 11.5:

(i) The transferee shall have no right to vote or participate in the management of the business, property, and affairs of the Company, or to exercise any rights of or to become a Member; and

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