William E. Gustashaw, Jr. v. Commissioner of IRS

696 F.3d 1124, 87 A.L.R. Fed. 2d 771, 2012 WL 4465190, 110 A.F.T.R.2d (RIA) 6169, 2012 U.S. App. LEXIS 20379
CourtCourt of Appeals for the Eleventh Circuit
DecidedSeptember 28, 2012
Docket11-15406
StatusPublished
Cited by38 cases

This text of 696 F.3d 1124 (William E. Gustashaw, Jr. v. Commissioner of IRS) is published on Counsel Stack Legal Research, covering Court of Appeals for the Eleventh Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
William E. Gustashaw, Jr. v. Commissioner of IRS, 696 F.3d 1124, 87 A.L.R. Fed. 2d 771, 2012 WL 4465190, 110 A.F.T.R.2d (RIA) 6169, 2012 U.S. App. LEXIS 20379 (11th Cir. 2012).

Opinion

HULL, Circuit Judge:

Although a tax shelter can be legitimate, Petitioner William Gustashaw, Jr., 1 participated in one that was not. Gustashaw claimed substantial tax benefits from the shelter on four consecutive tax returns. The IRS later disallowed Gustashaw’s claim and determined deficiencies in tax and accuracy-related penalties, including gross valuation misstatement penalties and a negligence penalty. Gustashaw conceded the deficiencies in tax, but contested the penalties. The Tax Court affirmed the IRS’s imposition of the penalties. After review and oral argument, we affirm.

I. BACKGROUND

A. Gustashaw’s Education and Business Background

Petitioner Gustashaw is a college-educated, successful businessman. Gustashaw, who married his wife Nancy in college, graduated from Gannon University in 1973 with a bachelor of science degree in industrial management. While in college, Gustashaw took business-related courses, including managerial cost accounting and the principles of accounting.

Following graduation, Gustashaw embarked on a nearly thirty-year business career. From 1973 to 1993, Gustashaw held management positions with various companies in the food and beverage industry. Then, in 1994, Gustashaw became vice-president of operations at Merck Medco Managed Care (“Merck Medco”) in Tampa, Florida. As vice-president of operations, Gustashaw was responsible for large-scale prescription processing in a mail-order pharmacy. Subsequently, Merck Medco promoted Gustashaw to vice-president and general manager, which expanded his responsibilities to all operations of two mail-order pharmacies. *1127 Merck Medco also provided Gustashaw with generous stock options.

B. Gustashaw’s Early Retirement Plan

In 1995, Gustashaw, who was then 45 years old, began planning for an early retirement. Gustashaw had a conservative investment history and handled nearly all of his and his wife’s investment decisions himself. In addition, Gustashaw had filed all of the couple’s joint federal income tax returns. However, to assist with his retirement plan, Gustashaw decided to hire a financial planner.

To that end, Gustashaw hired Ralph Maulorico, a financial planner at New England Financial who represented wealthy individuals. Gustashaw wanted to exercise his Merck Medco stock options by 2000, and sought Maulorico’s advice on whether the stock option exercise would generate enough income to fund the Gustashaws’ retirement. Maulorico recommended the stock option exercise. Thus, in 1996, Gustashaw sold some of the acquired stock and invested the proceeds in mutual funds.

The next year, 1997, Gustashaw decided to hire a tax accountant to review the Gustashaws’ tax returns, which Gustashaw would continue to prepare until 2000. On Maulorico’s recommendation, Gustashaw hired William Gable, Maulorico’s college friend. Gable, who owns an accounting practice in Florida, is an enrolled agent and accountant, but not a certified public accountant. Gable received both an undergraduate and a master’s degree in accounting, with the master’s degree specializing in taxation, at LaCrosse University. Gable reviewed the Gustashaws’ self-prepared joint returns for 1997 through 1999, before they were filed.

In 1999, Merck Medco underwent a reorganization and offered Gustashaw an option to retire early. Gustashaw accepted and retired that same year. The following year, 2000, Gustashaw exercised his remaining Merck Medco stock options and sold the stock, generating $8,077,376 in income. For that year, Gable prepared the tax return, at Gustashaw’s request. The 2000 return claimed tax benefits through a complicated financial transaction known as “CARDS,” as explained in the next section.

C. The CARDS Tax Shelter

In early 2000, Maulorico learned from a colleague about the Custom Adjustable Rate Debt Structure (“CARDS”) transaction and its use as a tax shelter. The colleague learned of the CARDS transaction through Roy Hahn, a certified public accountant and founder of Chenery Associates, Inc. (“Chenery”). Chenery developed and promoted the CARDS shelter. At the time, Maulorico, who had experience in tax shelters, believed the transaction offered both profit potential and a tax shelter for the income from Gustashaw’s stock option exercise. Thus, Maulorico suggested the CARDS transaction to Gustashaw, who became interested in it.

During the 1990s and early 2000s, the CARDS transaction was promoted to high net worth individuals both as an investment-financing mechanism and a tax shelter. In the CARDS transaction, a U.S. taxpayer, facilitated by a newly created company, uses a bank loan to create a tax loss based on an artificially high basis (or cost) in assets, which then allows the taxpayer to generate a tax benefit by offsetting real, taxable income.

There are three steps to create the CARDS tax shelter. 2 First, in the loan *1128 origination step, a foreign bank loans currency to the borrower, a Delaware limited liability company owned 100% by nonresident alien individuals. Importantly, the foreign ownership of the borrower ensures the borrower is not subject to U.S. taxation. The loan is for a 30-year term with annual interest payments due, but not principal payments. The bank deposits the loan proceeds directly into the borrower’s account at the bank. However, to use the loan proceeds, the borrower must meet collateralization requirements by acquiring valuable, stable assets such as government bonds.

Second, in the loan assumption step, a U.S. taxpayer and the borrower enter into an agreement whereby the U.S. taxpayer assumes joint and several liability for the borrower’s entire loan. In exchange, the U.S. taxpayer receives only a small percentage of the loan proceeds from the borrower, e.g., 15% for our purposes. The borrower agrees to retain all interest obligations, and the U.S. taxpayer agrees to repay the unpaid principal amount. The U.S. taxpayer then could, in theory, use the assumed loan proceeds to make an investment, but the bank maintains discretion on whether to release any funds. To access the loan proceeds, the U.S. taxpayer must deposit equivalent, substitute collateral with the bank.

And third, in the currency exchange step, the U.S. taxpayer exchanges his 15% portion of the foreign-currency loan for U.S. dollars. This currency exchange is a taxable event generating tax benefits. To achieve the benefits, the U.S. taxpayer claims that his basis in the exchanged currency is the entire amount of the loan, not the 15% of the loan that the taxpayer actually received from the tax-exempt borrower. This discrepancy creates a permanent tax loss of 85% of the original loan amount, which permits the U.S. taxpayer to shelter other unrelated, taxable income.

In August 2000, the Internal Revenue Service (“IRS”) issued a notice warning taxpayers against claiming tax benefits through tax shelters similar to the CARDS shelter, because such benefits would be subject to penalties. See I.R.S. Notice 2000^4, 2000-2 C.B. 255. In March 2002, the IRS issued another, similar notice that was targeted specifically at the CARDS shelter. See

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696 F.3d 1124, 87 A.L.R. Fed. 2d 771, 2012 WL 4465190, 110 A.F.T.R.2d (RIA) 6169, 2012 U.S. App. LEXIS 20379, Counsel Stack Legal Research, https://law.counselstack.com/opinion/william-e-gustashaw-jr-v-commissioner-of-irs-ca11-2012.