T.C. Memo. 2021-76

UNITED STATES TAX COURT

MICHAEL R. KELLY, Petitioner v.

COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket Nos. 6225-16, 16847-16. Filed June 28, 2021.

Kevan P. McLaughlin and Phillip L. Jelsma, for petitioner.

Monica D. Polo, Donna L. Crosby, Vladislav M. Rozenzhak, Monica

Cendejas, and Clinton M. Crosser, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

GOEKE, Judge: In these consolidated cases, respondent issued two notices

of deficiency determining the following deficiencies and penalties:

Served 06/28/21
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Year Deficiency

Penalty

sec. 6663

2007 $6,723,181 $4,505,289

2008 3,359,322 2,460,017

2009 1,481,917 1,051,239

2010 27,953,488 20,897,162

2011 158,661 118,996

In the alternative to the fraud penalties, respondent determined 20%

accuracy-related penalties under section 6662(a)1 for each of the years at issue. 

Various smaller issues included in the above deficiency determinations have

been settled, and Mr. Kelly chose not to challenge several other smaller issues on

brief. The principal issues remaining in dispute involve Mr. Kelly’s transfers of

funds between corporations he owned and the tax treatment of those transactions. 

The transactions are factually complex. For the first three years there are statute of

limitations issues and determinations of fraud. Respondent has conceded the

penalties for tax years 2010 and 2011 because he did not establish that written

supervisory approval was obtained as required by section 6751(b).

[*2]

1Unless otherwise indicated, all section references are to the Internal

Revenue Code, title 26, U.S.C., in effect for the years at issue, and all Rule

references are to the Tax Court Rules of Practice and Procedure. Some dollar

amounts are rounded. 
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[*3] The issues remaining for decision are more specifically stated as follows.

(1) Were transfers from National Service Industries, Inc. (NSI), to Kelly

Capital, LLC (Kelly Capital), bona fide loans, or should the amount by which the

transfers exceeded Mr. Kelly’s adjusted basis in NSI be treated as taxable capital

gain for the respective tax years? This issue further relates to the broader question

of whether the funds transferred to Mr. Kelly and his companies were bona fide

loans or should be treated as distributions. We hold that transfers after 2007 were

not loans but rather distributions valued at the face amounts of the funds

transferred.

(2) To the extent that the funds transferred to Mr. Kelly and his companies

were bona fide loans, did Mr. Kelly receive taxable distributions when the loans

were canceled, and if so, what was the value of the distributed property? We hold

that Mr. Kelly received taxable distributions to the extent we have found that the

loans were bona fide and the distribution amounts are the face values of the loans.

(3) For tax year 2010, to the extent that loans existed, did Mr. Kelly have

taxable cancellation of debt (COD) income, or was he insolvent such that the

discharge of indebtedness is not includable in his gross income under section

108(a)(1)(B)? We hold that Mr. Kelly’s insolvency computation for 2010 requires

the elimination of loans to him from his closely held companies. Accordingly, we
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[*4] hold that his COD income is overstated, and the parties must compute the

insolvency amount in the Rule 155 computations in accordance with our holdings

herein.

(4) Inextricably linked to the first three issues is the question of whether Mr.

Kelly is entitled to a nonbusiness bad debt deduction for tax year 2010. We hold

Mr. Kelly has not established that he is entitled to a nonbusiness bad debt

deduction.

(5) For tax years 2010 and 2011, did Kelly Capital have additional taxable

income on the basis of deposits in its bank accounts, or were the deposits from

bona fide loans or other nontaxable sources? We hold there was no additional

income.

(6) For tax year 2009, is Mr. Kelly entitled to a loss deduction for forgiven

loans made primarily to his brother and the Bitter End, Inc. (TBE)? We hold Mr.

Kelly has failed to establish such a deduction should be permitted.

(7) For tax year 2010, is Virtucon, LLC (Virtucon), allowed to deduct

$1,482,334 in interest related to its ownership of an airplane? We hold the

deduction is not proper.
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[*5] (8) For tax years 2010 and 2011, is Kelly Yacht & Charter, Ltd. (KY&C),

entitled to deduct various expenses including those paid with borrowed funds?

We hold the deductions are proper.

(9) For tax year 2010, are the following deductions allowed for Lemon Bay

Horizons, LLC (LBHorizons), the developer of several Florida condominiums?

Expense Amount

Interest/other $156,405

Taxes and licenses 53,314

Other 19,943

We hold this treatment is proper.

(10) For tax years 2010 and 2011, is Mr. Kelly entitled to passive activity

loss deductions from Front Street Investment Fund, LLC (FSIF), to net against

passive activity income? Similarly, for tax year 2010, is Mr. Kelly entitled to

deduct suspended and unused passive activity losses from Radius Mortgage

Capital, LLC (Radius Mortgage)? The deductions are allowed to the extent

allowable in the Rule 155 computations.

(11) Has respondent proven, for tax years 2007, 2008, and 2009, by clear

and convincing evidence, that Mr. Kelly underpaid his tax and that some part of

the underpayment for each year was due to fraud? In the alternative to the section
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[*6] 6663 fraud penalty for tax year 2009, is Mr. Kelly liable for an accuracyrelated penalty under section 6662(a)? We hold the fraud penalty is not sustained

for 2007, 2008, or 2009 and further hold that if there is a 25% omission from gross

income for 2009, the section 6662(a) penalty applies for that year.

(12) For tax years 2007, 2008, and 2009, did respondent timely issue the

notice of deficiency under section 6501(a)? We hold that the deficiency notice is

untimely for 2007 and 2008 and the status for 2009 depends on whether a 25%

omission of gross income under section 6501(e)(1) is sustained in the Rule 155

computations. 

(13) Was Mr. Kelly’s failure to timely file Forms 5471, Information Return

of U.S. Persons With Respect to Certain Foreign Corporations, for tax years 2008

and 2009 the result of reasonable cause and not willful neglect? We hold there

was reasonable cause. 

All other unsettled issues are computational.

2

 

2To the extent that the unaddressed issues are unresolved and are not

computational, Mr. Kelly has conceded them on the basis of his failure to address

them on brief, including losses reported on Schedules E, Supplemental Income

and Loss, attached to his personal returns for 2010 and 2011.
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[*7] FINDINGS OF FACT

The parties have stipulated facts which are incorporated herein by this

reference. When the petitions were timely filed, Mr. Kelly resided in California. 

Mr. Kelly’s first experience in buying and selling companies came when he

bought a sporting goods store for $25,000 in the 1980s that he successfully resold

for a $50,000 profit. In the early 1990s Mr. Kelly’s father purchased a $150

million portfolio of loans from a bankruptcy receiver for $75 million and asked

Mr. Kelly to join him in reselling the loans. Mr. Kelly moved from California to

Arizona and began to learn the process of flipping loans under the tutelage of his

father and Robert Jacobson, a lawyer assisting in the transactions. 

Mr. Kelly visited various banks, met with their presidents or managers, and

tried to resell the loans for more than the discounted purchase prices. Mr. Kelly

developed a personal and professional relationship with the owners of one such

bank, Mountain Community Bank, which would become one of Mr. Kelly’s future

lenders. Mr. Kelly was paid 5% of net proceeds from the sale of the loans for his

efforts. Mr. Kelly’s understanding of flipping loans progressed, and he was soon

able to capitalize on other loan portfolios. He began bidding on smaller loan

portfolios. While working for his father, Mr. Kelly began collecting from some
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[*8] debtors, working out loans with borrowers, or taking ownership of the

underlying property in foreclosure.

I. Early Business Operations

Sometime around 1993 Mr. Kelly and his father’s business relationship

deteriorated. Mr. Kelly returned to California and began a similar loan trading

business with his brother, Richard. In August 1993 the brothers set up First

Commercial Corp. (FCC), an S corporation, with each brother owning an equal

share. Over time, Mr. Kelly’s ownership of FCC increased. By 2009 Mr. Kelly

owned 66.1% and Richard owned 33.9%, and in 2010 and 2011 Mr. Kelly owned

75% and Richard owned 25%. 

One of the brothers’ first businesses was a San Diego bar. In or around

1995 Mr. Kelly identified a local bar, the Orient, as a possible business venture. 

On January 10, 1995, the brothers organized a special purpose entity, TBE, to

purchase and hold the liquor license and to operate the bar. Mr. Kelly borrowed

$250,000 from FCC to purchase the liquor license. TBE borrowed $2 million

from Mountain Community Bank to renovate the bar’s three-story building. FCC

and Mr. Kelly personally guaranteed the loan. The loan was eventually repaid. In

2007 and 2008, Mr. Kelly owned 51% of TBE and Richard owned 49%. During
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[*9] 2009 Richard’s ownership increased to 77.6%, Mr. Kelly owned 18.2%, and

three other individuals owned the remainder. 

Another joint venture of the brothers was Lucky Bastard Records, LLC

(Lucky Bastard Records), a company established to produce and promote a band. 

Mr. Kelly and Richard each owned 50% of Lucky Bastard Records. FCC

advanced money to Lucky Bastard Records, which FCC recorded as a debt, and as

of December 31, 2007, Lucky Bastard Records owed $952,393 to FCC. For tax

year 2007, Mr. Kelly reported over $75,000 of nonpassive income attributable to

Lucky Bastard Records.

A. Nonperforming Loans

In the late 1990s Mr. Kelly began focusing his investment activity on assets

used as security for nonperforming loans and the value of the assets relative to the

loans’ values. The underlying assets became more important. Mr. Kelly engaged

in some of these ventures through FCC and in others on his own. The assets

typically included a business entity with associated real estate. Mr. Kelly would

foreclose on the collateral, make improvements to the business and property, and

then either operate the business or resell it. Mr. Kelly initially borrowed money

from third-party lenders to finance the purchase of the nonperforming loans. Mr.

Kelly obtained loans from his old friends at Mountain Community Bank. He also
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[*10] obtained loans from Fremont Investment & Loan, Fortress,

3

 and First

American Bank. He developed a history of repaying these lenders and reinvesting

the remaining sale proceeds in his next business venture. He approached each

deal with the plan to use the proceeds to finance the next, hopefully bigger, deal,

with many successful sales of his business investments.

In a typical transaction, Mr. Kelly would, in part at the request of the

lenders, set up two special purpose entities: one to own the foreclosed real estate

and one to manage any business operations connected with the real estate. One of

the goals was to isolate the risks from the business operations from the real estate,

which the lenders generally valued more. Ultimately, FCC traded over $3.3

billion in loans and real estate between 1993 and 2003 and acquired numerous real

estate projects throughout California including residential developments in Orange

Grove, residential lots in Moreno Valley, lots in Rainbow, vacant office buildings,

and strip-mall shopping areas. 

In 2004 Mr. Kelly decided to start his own company without his brother, to

operate the same way that FCC had operated. On September 29, 2004, Mr. Kelly

organized Kelly Capital as a single-member limited liability company (LLC). Mr.

3The record refers to loans from and/or assigned by or to Fortress Credit

Corp., Fortress Investment, and Fortress Financial. For convenience, we refer to

these three entities collectively as Fortress.
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[*11] Kelly was the sole member from its organization through the years at issue. 

He shifted FCC’s activities and employees to Kelly Capital. However, FCC

continued in existence. FCC’s records for 2007 reflected $3,883,567 and

$4,462,446 due from these entities, respectively, which FCC wrote off as bad

debts for the 2007 tax year. 

Ultimately, Mr. Kelly set up over 25 closely held companies, many as

single-member LLCs, that he owned and controlled (affiliated companies). He

began to transfer money between his affiliated companies to fund his business

ventures and recorded the transfers as loans. He did not cause his single-member

LLCs to file entity-level returns. Instead, he reported the tax items of each singlemember LLC on a Schedule C, Profit or Loss From Business, attached to his

personal return. For 2007 Kelly Capital reported a profit of approximately $2.7

million with receipts of $13 million. However, for 2008, 2009, and 2010 it

reported losses of $1.5 million, $8 million, and $1.1 million, respectively, with

gross receipts of $2 million, $500,000 and $4 million, respectively.

B. Accounting Activities

FCC used the nomenclature “due to” and “due from” to track how much

money was owed between Mr. Kelly’s affiliated companies. Initially, FCC used

the outside accounting services of Robert Regnery at Kenneth Leventhal & Co.,
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[*12] who later became FCC’s chief financial officer (CFO). Mr. Regnery likely

introduced the “due to” and “due from” method to track the transfers between Mr.

Kelly’s affiliated companies. Mr. Kelly’s affiliated companies consistently

adhered to this method to track transfers during the years at issue. In 1994 FCC

hired Joseph Thomas as a staff accountant. He was transferred to Kelly Capital,

where he worked during the years at issue. In his early role, he was the person on

the accounting staff to record these transactions. Later, he served as vice president

and senior vice president controller, and his responsibilities consisted of

overseeing the company’s cashflow, financials, bank reconciliations, and

investments to ensure the information that was provided to Mr. Kelly for financial

reports was accurate. Mr. Thomas typically prepared Mr. Kelly’s personal

financial statements.

Over the decades of their operations, Mr. Kelly’s companies developed

accounting departments that employed qualified professionals. They also

employed in-house legal counsel. In 1999 Charles Blottin replaced Mr. Regnery

as FCC’s CFO, and he eventually moved to Kelly Capital. In August 2005 Mr.

Bowen replaced Mr. Blottin and served until his departure around December 2018. 

Mr. Bowen has been a certified public accountant (C.P.A.) since 1984 and has an

extensive career as an accountant. Mr. Thomas reported to the CFOs including
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[*13] Mr. Bowen. Michael Marks, an attorney, worked for FCC and later Kelly

Capital from 2002 to 2012, serving as general counsel during most of that time

except for when Louis Alonso served as general counsel during 2007 through

2009.

II. Mr. Kelly’s Business Ventures

In 1997 Mr. Kelly purchased a $28 million nonperforming loan secured by a

hotel in Kauai, Hawaii, for $2.8 million. He foreclosed on the loan. Pacific Rim

Partners was organized to own the hotel, and Pacific Coast Partners, LLC (Pacific

Coast), was organized to manage the hotel; it changed the name to Kelly

Hospitality, LLC (Kelly Hospitality), in 2007. From the date of registration,

October 31, 1997, through December 31, 2011, Mr. Kelly was the sole member of

Pacific Coast and Kelly Hospitality. For convenience we refer to these two

entities collectively as Kelly Hospitality.

In 1998 Mr. Kelly acquired a nonperforming loan secured by 1,868 acres of

real estate in Julian, California. Mr. Kelly borrowed roughly $3 million to acquire

the loan and then foreclosed on the property. On February 10, 1998, Julian

Country Estates, LLC (JCE), was organized to own the real estate, with Mr. Kelly

and Richard each owning 50%. Around 2002 JCE sold the real estate for roughly
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[*14] $9.2 million, and Mr. Kelly reinvested the proceeds in a hotel adjacent to

TBE’s bar known as the Ivy Hotel, discussed further below.

Another business venture of Mr. Kelly was Fat City, a 140,000-square-foot

family entertainment center in Littleton, Colorado, which FCC acquired by

purchasing a $25 million nonperforming loan for roughly $2 million. On January

1, 1999, Greenback Holdings, LLC (Greenback Holdings), was organized as a

special purpose entity to hold the entertainment center. Cutthroat Entertainment,

Inc., which later changed its name to Greenback Entertainment, Inc. (Greenback

Entertainment), an S corporation, was organized to manage and operate the

business, separating the ownership of the real estate and the management of

business operations in two entities in accordance with Mr. Kelly’s typical practice. 

Mr. Kelly and his entities borrowed roughly $10 million and invested it in Fat City

and operated the business for seven years. Around 2008 Mr. Kelly sold Fat City,

used the proceeds to repay existing liabilities, and reinvested the remaining funds

in his other businesses. Greenback Entertainment continued in existence, and

during 2009 through 2011 it was wholly owned by Mr. Kelly. Greenback

Entertainment recorded intercompany transfers to and from Mr. Kelly’s affiliated

companies including a $1.7 million transfer to Kelly Capital. As of the end of
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[*15] 2010, Greenback Entertainment had amounts due to Kelly Capital of

approximately $2 million according to Kelly Capital’s records.

In another transaction, Mr. Kelly purchased a nonperforming loan secured

by a golf course near Modesto, California, and foreclosed on the property. Hidden

Hills Holdings was organized as the special purpose entity to own the golf course,

and Hidden Hills Resort was organized to operate the golf course. Initially, Mr.

Kelly and Richard each owned 50% of Hidden Hills Holding, and Mr. Kelly

owned 100% of Hidden Hills Resort. Mr. Kelly renovated the property, installing

cart paths and fixing up the club house to increase golfer traffic. Mr. Kelly

eventually sold the golf course, apparently at a loss. FCC transferred money to

Hidden Hills Holdings and Hidden Hills Resort.

In June 2003 Mr. Kelly acquired his first publicly traded company, NSI, a

Delaware corporation (NSI-DE), for $113 million (NSI acquisition), with the

intention of liquidating its assets and investing the proceeds in other business

ventures. Mr. Kelly borrowed the purchase price from institutional lenders and a

private investor. He personally guaranteed these loans. He gave a 5% ownership

interest in NSI-DE to David Nicolas Spriggs II to compensate Mr. Spriggs for his

work in identifying NSI-DE as a possible target and his assistance with the

acquisition process. Mr. Spriggs had been working with Mr. Kelly and Richard
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[*16] since 1999. Around the time of the NSI acquisition, Mr. Kelly organized

Kelly Capital as a single-member LLC, and on January 26, 2007, he transferred his

95% interest in NSI-DE to Kelly Capital. 

At some point, Mr. Kelly caused NSI-DE to organize a California

corporation by the same name as a wholly owned subsidiary (NSI-CA). NSI-DE

and NSI-CA filed consolidated S corporation returns for the years at issue. In May

2012 NSI-CA changed its name to Englewood Holdings Corp. (Englewood). We

refer to the Delaware parent company as NSI-DE, the California subsidiary as

NSI-CA, and the two entities collectively as NSI.

Before 2001 NSI was a diversified conglomerate engaged in various

businesses. In 2001 NSI decided to spin off various businesses into a separate

publicly traded company. When Mr. Kelly acquired NSI-DE, its business

operations were unprofitable but it had approximately $20 to $30 million cash on

hand. It primarily engaged in two business areas, textile rentals and envelope

manufacturing. NSI-DE’s textile rental activity provided napkins, table and bed

linens, bath towels, pillowcases, bar towels, scrubs and surgical cloths, mats,

mops, and restroom supplies to dining, lodging, and healthcare customers through

National Linen & Uniform Service, LLC (National Linen). The envelope

manufacturing activity made custom envelopes for clients in the energy, finance,
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[*17] transportation, direct mail, and package delivery markets through Atlantic

Envelope Co., LLC (Atlantic Envelope). National Linen and Atlantic Envelope

operated roughly 77 plants, almost exclusively east of the Mississippi River, and

had roughly 6,500 to 7,500 employees. 

At one time NSI-DE owned North Brothers, Inc. (North Brothers), a

regional distributor of asbestos-containing insulation primarily in the southeastern

United States and became subject to claims of liabilities related to the asbestos

products sold or installed by North Brothers. Between 1972 and 2002 NSI-DE

received over 187,000 asbestos claims including 57,775 claims filed in 2001 and

2002. As of December 31, 2002, 25,466 claims were still pending. Claims

continued to be filed after the NSI acquisition and as of August 31, 2005, there

were 41,700 open or pending asbestos claims. As of July 12, 2012, the number of

pending asbestos claims had shrunk to approximately 28,258.

In 1985 NSI entered into an agreement with 31 other producers of asbestos

or asbestos-containing products and 16 insurers, known as the Wellington

Agreement. Under its terms the Asbestos Claims Facility (ACF) was created as a

nonprofit claims handling center that coordinated claim payments on behalf of

dozens of asbestos defendants. The parties to the Wellington Agreement, like

NSI-DE, sought to reduce asbestos litigation awards while lowering the associated
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[*18] costs by agreeing to an allocation formula for all claims whereby each party

agreed to pay a share of every settled or adjudicated asbestos claim asserted

against one or more Wellington Agreement parties in accordance with a producer

allocation formula whether or not the claimant alleged exposure to the party’s

asbestos products. Thus, the Wellington Agreement avoided the need to assert

cross-claims against asbestos producers in the underlying asbestos lawsuits and

drove down associated defense costs. 

On October 6, 1988, the Center for Claims Resolution, Inc. (CCR), was

organized to replace ACF, which was officially dissolved on October 3, 1988. 

The CCR subsequently disbanded in early 2001. Since February 1, 2001, NSI-DE

directly retained attorneys to defend itself from asbestos claims, engaging a law

firm to serve as national counsel to coordinate local attorneys to defend NSI from

asbestos claims in the jurisdictions where they arose. NSI-DE also engaged a

claims processing and administration services. 

As part of the NSI acquisition due diligence Mr. Kelly, by and through his

counsel, requested a review of NSI-DE’s asbestos liabilities, related insurance

coverage, and other financial considerations. On March 19, 2003, Peterson

Consulting issued an analysis of NSI’s asbestos liabilities (Peterson Consulting

report). The Peterson Consulting report estimated that NSI would pay between
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[*19] $240 and $262 million for indemnity costs and $49 and $81 million for

defense costs to resolve all pending and future asbestos claims filed through 2012. 

The report also concluded that all but $16 million of NSI-DE’s asbestos liabilities

through 2014 would be covered by solvent insurance providers. Specifically, the

Peterson Consulting report concluded by stating:

Based on our independent review of NSI’s historical claims data, our

evaluation of NSI’s pending claims, and our estimates of NSI’s future

asbestos claims filings through 2012, we believe that NSI will

continue to incur liability associated with asbestos bodily injury

claims for the next 50 years. We estimate the range of total liability

incurred by NSI for asbestos bodily injury claims from 2003 through

2014, from claims filed through 2012, to be approximately $240

million to $262 million and from $49 million to $81 million for

defense payments, for a total of from $289 million to $343 million. 

We estimate that all but $16 million of this amount will be covered by

insurance provided by insurers that are currently solvent. 

As part of the NSI acquisition, Mr. Kelly obtained two appraisals of NSIDE. On March 31, 2003, Houlihan, Lokey, Howard & Zukin, Inc., prepared an

analysis of NSI-DE’s value which determined that as of the date of the report NSIDE’s assets exceeded its stated and contingent liabilities and concluded NSI-DE

“should be able to pay its debts as they become absolute and mature.” On June 12,

2003, Jefferies & Co., Inc., issued an analysis of NSI-DE’s solvency and likewise

concluded that NSI-DE’s assets exceeded its stated and identifiable contingent
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[*20] liabilities (which included the asbestos claims) and it “should be able to pay

its debts as they mature.” 

When the NSI acquisition was completed, NSI-DE had over $1 billion in

insurance coverage and equity in its assets, which would have been sufficient to

pay its asbestos liabilities in full. It had virtually no debt besides the accrued

asbestos liabilities. It owned numerous plants and equipment, free and clear,

valued at roughly $150 million. After the NSI acquisition, Mr. Kelly continued to

operate National Linen and Atlantic Envelope. However, in 2005 he began to sell

off divisions of National Linen and completed the sale of National Linen in 2006

for a total of roughly $205 million. Also in 2006, NSI sold Atlantic Envelope for

approximately $70 million. Mr. Kelly used the sale proceeds, along with interim

operating income and cashflow, to fully repay the loans that he had obtained to

finance the NSI acquisition. After repayment of the loans, NSI-DE had cash on

hand. Although it continued to have asbestos liabilities, Mr. Kelly expected them

to be fully covered with existing insurance. Accordingly, Mr. Kelly made a

decision to use NSI-DE as his quasi-bank to finance his other business ventures. 

He had approached the NSI acquisition with the same basic plan as his prior

investments, to strip cash from NSI-DE primarily through loans to his other

business ventures set up as separate companies. He believed the cash available in
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[*21] NSI-DE was basically his money that could be lent to his affiliated

companies. He used both NSI-DE and NSI-CA to transfer funds to his affiliated

companies.

NSI-DE had uninsured asbestos liabilities and the need to retain cash

reserves on its balance sheets as a source to fund payment of asbestos claims. 

Accordingly, Mr. Kelly recorded the transfers from NSI to his affiliated companies

as loans as a tool to keep NSI-DE’s balance sheet static, thereby pacifying

asbestos plaintiff lawyers, while putting the cash to work and earning returns from

investing in other deals. 

III. Intercompany Transfers

It was after completing the NSI acquisition that Mr. Kelly decided to

organize Kelly Capital to engage in investment activities without his brother and

began to conduct most of his business ventures through Kelly Capital. Mr.

Spriggs served as executive vice president and later as president. At the time of

the NSI acquisition, NSI-DE had its own accounting department, and its

accounting records initially continued to be controlled by its own accounting staff

and CFO. At some point, the accounting records and responsibilities were

transferred to Kelly Capital. 
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[*22] During 2004 though 2007 Mr. Kelly organized three more entities as part of

his business investment activities. In July 2004 he organized FSIF with Mr.

Spriggs. Kelly Capital initially owned 95% of FSIF, and Mr. Spriggs owned 5%. 

FSIF was organized after questions were raised about a $23.8 million transfer from

NSI-DE to FCC. As a result of these questions the transfer was recorded as a

transfer from NSI-DE to FSIF and then from FSIF to FCC. NSI-DE transferred

additional amounts to FSIF during 2005 and FSIF repaid approximately $6.2

million during 2006. As of the end of 2006 there was an outstanding balance in

NSI-DE’s books and records of at least $33.7 million due from FSIF. On June 25,

2007 Mr. Spriggs sold his 5% interest in FSIF to Kelly Capital and Kelly Capital

became FSIF’s sole member.

On August 28, 2005, Mr. Kelly organized Kelly Capital Investments, LLC

(Kelly Investments), with Kelly Capital as its sole member. Around that time Mr.

Kelly began to transfer funds from NSI-DE and NSI-CA to Kelly Capital and

Kelly Investments instead of FCC. On May 30, 2006, Mr. Kelly organized Kelly

Finance, LLC (Kelly Finance), with Kelly Capital as its sole member. Kelly

Finance’s business activity was minimal, and its existence terminated in July 2009.

Between 2004 and March 2011 NSI transferred approximately $175 million

to Mr. Kelly and his affiliated companies that NSI characterized as loans in its
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[*23] books and records. During 2004 through 2006 NSI transferred

approximately $57.2 million to Mr. Kelly and his affiliated companies including

the $33.7 million that was recorded as loans to FSIF as of the end of 2006. From

2007 to 2010 NSI transferred approximately $100 million to Kelly Capital and

Kelly Investments which NSI characterized as loans as follows:

4

Year Borrower Amount

2007 Kelly Capital $41,230,000

2008 Kelly Capital 21,537,259

Kelly Investments 17,536,486

2009 Kelly Capital 17,089,996

2010 Kelly Capital 3,451,696

Kelly Capital and Kelly Investments executed promissory notes for the

transfers from NSI that provided for interest at the short-term Federal rate of

interest. The accrued interest was tracked in NSI’s records. Mr. Kelly did not

have interest charged or accrued on loans between his single-member LLCs.

During 2007 Kelly Capital repaid approximately $6.2 million of the transfers. 

4We base our findings on a table attached to respondent’s brief as Mr. Kelly

has conceded on brief that the amounts of the transfers set forth in the table are

correct.
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[*24] During 2007 through 2010 NSI also transferred approximately $16.7 million

directly to Mr. Kelly, which NSI recorded as loans.

IV. Business Ventures After NSI Acquisition

A. Ivy Hotel

In May 2002 Mr. Kelly purchased a hotel adjacent to TBE’s bar with the

proceeds from the sale of JCE’s real estate for $7.8 million with the idea of

renovating it into a boutique hotel known as the Ivy Hotel. Ivy Hotel, LLC,

initially known as 630 F Street, LLC (IHSD), was organized to own the hotel. 

IHSD was wholly owned by JCE. Mr. Kelly also acquired an apartment building

with retail shops on the first floor that was adjacent to TBE’s bar and abutted the

hotel. Mr. Kelly organized Gaslamp Partners as a special purpose entity to own

the apartment building. Mr. Kelly tore down the building to use the land as a

parking lot for the hotel.

In March and May 2003 IHSD received offers to buy the hotel for $13.75

million, which would have resulted in an approximately $5.6 million profit. Mr.

Kelly declined these offers because he believed that he could renovate the hotel

and sell it for a greater profit. To finance the renovations, Mr. Kelly obtained a

$48.5 million construction loan from Fortress. On December 9, 2005, IHSD

(together with other entities that Mr. Kelly controlled including Kelly Hospitality)
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[*25] entered into a loan and security agreement with Fortress (IHSD construction

loan). Mr. Kelly and Richard personally guaranteed the loan. The loan was

secured by the hotel itself and JCE, as well as other properties owned by Mr. Kelly

and FCC. Mr. Kelly embarked on the considerable project of completely gutting

and renovating the 20,000-square-foot building. On June 6, 2007, IHSD together

with the other obligors of the IHSD construction loan entered into an amendment

of the loan and security agreement that increased the maximum loan amount to

$65 million. Mr. Kelly also used approximately $44 million from Kelly Capital

for construction costs.

When construction on the hotel finished in mid-2008, the new Ivy Hotel

was a four-story hotel with a basement banquet facility, meeting rooms, and a

rooftop pool and bar. After completion Mr. Kelly and his entities ran the food and

beverage services at the Ivy Hotel and an outside management company ran the

hotel operations. Unfortunately, the Ivy Hotel suffered with financial difficulties

quickly after construction was completed. In late 2008 Mr. Kelly attempted to sell

the newly finished hotel. He initially expected to sell it for $120 to $130 million,

but offers soon dropped to $80 to $90 million. In 2008 the hotel was appraised at

approximately $87 million.
- 26 -

[*26] Facing financial distress with continued ownership of the Ivy Hotel, Mr.

Kelly approached Fortress to address the crushing debt. In November 2008 Mr.

Kelly wrote to Fortress with an update of the Ivy Hotel’s financial status and his

inability to sell the hotel. Fortress put Mr. Kelly in contact with other boutique

hotel owners and operators. These contacts eventually culminated in a partnership

with Hyatt Hotels. As a result, the Ivy Hotel’s name was changed to the Andaz

Hotel. Andaz Hotel guaranteed IHSD’s payment obligations on the construction

loan for a period and made payments during the years at issue. 

In February 2010 IHSD and Kelly Hospitality, which was one of the

original obligors on the IHSD construction loan, entered into a second amendment

of the IHSD construction loan with Fortress. As a condition precedent to the

second amendment, Fortress required that IHSD provide additional collateral. Mr.

Kelly used various properties owned by his affiliated companies and his personal

residence as collateral. Among other things, the second amendment split the

existing $62 million into two loans of $50 million and $12 million. Mr. Kelly and

Richard personally guaranteed the two loans. The construction loan was

subsequently amended five more times, but at some point Fortress was no longer

willing to amend or to lend to Mr. Kelly and demanded he sell the hotel. On

March 4, 2013, the hotel was sold for $53 million, which was insufficient to fully
- 27 -

[*27] repay Fortress. When the hotel was sold, IHSD, Kelly Hospitality, and

Fortress amended the terms of the construction loan to provide for the repayment

of the remaining loan balance and the release of certain collateral. Mr. Kelly was

required to sign a deficiency note of $6 to $8 million, making him personally

liable for this amount.

In February 2009 Mr. Kelly converted the $44 million debt due from IHSD

to Kelly Capital into an equity interest in IHSD, and IHSD was released from

liability on the debt. Before that time Kelly Capital had no ownership interest in

IHSD. After February 2009 Kelly Capital owned 81.6% of IHSD and JCE owned

18.4%. Around that time Richard agreed to reduce his ownership interest in JCE

in exchange for the cancellation of debt recorded as due to Kelly Capital. During

2009 through 2011 Mr. Kelly owned 75% of JCE and Richard owned 25%. 

B. LBHorizons

On January 20, 2005, FSIF acquired LBHorizons for $4.5 million and the

assumption of LBHorizons’ $2.4 million bank loan. Mr. Kelly personally

guaranteed the loan. LBHorizons owned three real estate lots in Charlotte County,

Florida, that it planned to develop into 15 condominium units (condos). 

LBHorizons engaged a general contractor to finish the condo project and obtained

a $14.4 million construction loan that Mr. Kelly personally guaranteed. Mr. Kelly
- 28 -

[*28] also transferred funds to LBHorizons from his affiliated companies, and as

of December 31, 2010, LBHorizons had a balance of $6,418,852 due to Mr.

Kelly’s affiliated companies and $25,000 due to FCC. Mr. Kelly reported these

debts as discharged in 2010.

In 2008, 2009, and 2010 LBHorizons sold three, five, and seven condos,

respectively. For 2010 Mr. Kelly reported cost of goods sold by LBHorizons

relating to construction costs for the condos of $5,004,200, which respondent has

conceded is allowable. He also deducted an interest expense of $156,405, which

respondent disallowed in its entirety, and licenses and taxes of $11,386 and other

expenses of $33,577, of which respondent disallowed $53,314 and $19,943,

respectively.

C. Virtucon

On or around April 19, 2004, Virtucon was organized as a single-member

LLC to acquire an airplane. Mr. Kelly was the sole member of Virtucon during

the years at issue. On May 6, 2004, Virtucon purchased a 1988 Gulfstream

Aerospace GIV airplane and made improvements for a total cost of approximately

$12.3 million, financing the purchase with a bank loan. NSI-DE and Mr. Kelly

guaranteed the loan. Virtucon also paid $125,000 in broker’s fees and $16,225 in

title insurance as part of the purchase. Mr. Kelly purchased the airplane to allow
- 29 -

[*29] him and others to more efficiently visit Atlantic Envelope’s and National

Linen’s manufacturing plants. Mr. Kelly also used the airplane for personal

purposes, and he was not charged for his personal use, on the basis of a decision

by his accounting staff. 

Sometime in 2007 Mr. Kelly decided to charter the airplane to repay the

acquisition loan. Bob Freeman, Virtucon’s chief pilot, worked with brokers to

find potential customers. On June 23, 2008, Virtucon, Mr. Kelly, the Michael R.

Kelly Trust (MRK Trust), NSI-DE, and FCC entered into a loan agreement with

Bank of America to refinance the original purchase loan for $15,126,640, and

Virtucon executed a promissory note (Bank of America loan). Mr. Kelly, the

MRK Trust, and NSI-DE guaranteed the debt including various modifications and

forbearance agreements related to the security agreement.

As of December 31, 2008 and 2009, the outstanding balance on the Bank of

America loan was at least the initial principal amount, $15,126,640. In 2010 Bank

of America requested that Mr. Kelly sell or surrender possession of the airplane. 

On or around October 1, 2010, Bank of America, Mr. Kelly, FCC, and NSI-DE

entered into a loan modification agreement in which the borrowers (including Mr.

Kelly) agreed that the outstanding loan was $15,825,700, which (with rounding)

consisted of $14,710,329 of principal, $921,624 of accrued and unpaid interest,
- 30 -

[*30] and $193,746 of unpaid late charges. Mr. Kelly personally guaranteed the

loan modification. Virtucon later surrendered possession of the airplane to Bank

of America in partial satisfaction of the loan in the amount of $7.5 million,

reducing Virtucon’s indebtedness to $8.8 million. On January 9, 2012, Virtucon

and Bank of America entered into a mutual release and settlement agreement. In

April 2012 Virtucon’s existence terminated.

On Schedule C filed for Virtucon for 2010 Mr. Kelly deducted interest

expenses of $1,656,596 for amounts that were paid to Bank of America. 

Respondent determined that Virtucon paid $272,020 to Bank of America as

interest and disallowed the remainder. During 2010 Virtucon had received

transfers from Mr. Kelly’s affiliated companies of approximately $2.8 million.

D. KY&C

On or around February 21, 2008, KY&C was organized as a Cayman

Islands corporation to acquire a Cayman Islands-flagged yacht from a distressed

seller for roughly half of its original purchase price. In March 2008 KY&C

purchased the 131-foot yacht for approximately $9.4 million naming the yacht MY

Brazil. To fund the purchase, KY&C obtained an $8.1 million bank loan from

Wells Fargo. Mr. Kelly and Kelly Capital guaranteed the loan. Mr. Kelly paid the

remainder of the purchase price. Mr. Kelly completely refitted the vessel with the
- 31 -

[*31] expectation of selling or chartering it. In April 2008 KY&C contracted for

management services for the yacht, obtained a Federal employer identification

number, and registered to transact business in California. 

With no prospective buyer Mr. Kelly decided to charter MY Brazil, initially

in Europe. On March 11, 2009, KY&C engaged a charter marketing service and

shipped the yacht to Italy where it sat until a rogue wave smashed it into an

adjacent vessel. Litigation and insurance disputes prevented MY Brazil from

undocking. Unfortunately, the charter season had ended before it was allowed to

undock. Mr. Kelly returned MY Brazil to Florida and attempted to work out the

loan with the lender. 

KY&C did not make any payments on the loan. As of September 22, 2010,

the loan balance was the original principal, $8.1 million, plus interest. In May

2010 KY&C received an offer to purchase the yacht for $8 million and in early

2011 received two additional offers of $6 million and $5.3 million. Mr. Kelly

declined these offers. On February 22, 2011, Wells Fargo took possession of the

yacht and on November 23, 2011, sold it for $3.3 million. Around that time,

KY&C, Kelly Capital, and Mr. Kelly entered into a deficiency agreement with

Wells Fargo (2011 deficiency agreement), wherein the parties agreed that as of

January 31, 2011, the loan balance was $8,374,475, comprising approximately
- 32 -

[*32] $8.1 million in outstanding principal, $272,863 in unpaid interest, and

$1,612 in late charges.

Included in the 2011 deficiency agreement was an agreement that Wells

Fargo could pay protective advances to maintain MY Brazil. It provided:

Lender may pay such amounts as Lender in its sole discretion deems

appropriate for the protection and maintenance of the Property

including, without limitation, payment of the crew and captain

employed on the Vessel, payment of vendors and suppliers, payment

of maintenance and repair costs, payments of insurance premiums,

utility services, taxes, duties, tariffs, and all other fees and costs and

all other fees and costs the Lender deems necessary for the protection,

maintenance and rightful ownership of the Property. Any amounts so

paid shall be deemed “Protective Advances” and shall be secured by

the Security Documents and included in the Total Amount Due as

defined in Section 1 of this Agreement.

The 2011 deficiency agreement further provided that KY&C, Kelly Capital,

and Mr. Kelly were obligated to “first repay (i) the Initial Protective Advances and

(ii) any Current Taxes paid by the Lender, without discount and without

application of any proceeds from the sale of the Property.” KY&C, Kelly Capital,

and Mr. Kelly did not make any payments under the 2011 deficiency agreement

and on October 1, 2014, entered into an amended and restated deficiency

agreement. The amounts owed under this agreement were paid in full.

Mr. Kelly’s sole ownership of KY&C rendered it a controlled foreign

corporation subject to the reporting requirements of section 6038. No Form 5471
- 33 -

[*33] was timely filed for KY&C for tax year 2008 or 2009. In October 2019

respondent informed Mr. Kelly about the missing Forms 5471, and Mr. Kelly filed

the forms shortly thereafter. 

On the Schedules C filed for KY&C for 2010 and 2011 Mr. Kelly deducted

expenses that were paid with borrowed funds. For 2010 he deducted $782,542 in

expenses, and respondent disallowed $143,746 of the deductions including

$21,844 deducted for car and truck expenses. For 2011 he deducted $298,442 in

expenses and $111,591 for depreciation, and respondent disallowed all but $2,054

of the expense deductions and disallowed $27,874 of the depreciation deduction.

V. Failure of Businesses

By 2008 Mr. Kelly found it difficult to pay his creditors. He wanted to

avoid bankruptcy but found it impossible to pay third-party debt including loans

made by Fortress. At the end of 2007 he started to reduce debt owed between his

affiliated companies by writing off debt due to FCC. He also reduced the debt due

to NSI-DE by declaring dividends and distributing the debt to the shareholders. 

By 2008 the recapitalization of NSI was unrealistic. Mr. Alonso, Kelly Capital’s

general counsel, discussed filing bankruptcy with Mr. Kelly in 2008. Mr. Kelly’s

business ventures such as the Ivy Hotel were failing and did not provide a

reasonable prospect of repaying the advances from NSI. Yet Mr. Kelly continued
- 34 -

[*34] to advance approximately $20 million from NSI to Kelly Capital during

2009 and 2010. The situation was made worse by a subsequent $35.7 million

default judgment entered against NSI in an asbestos lawsuit in May 2011. 

A. Writeoff of Debt to FCC

As of December 31, 2007, FCC’s books reflected that there was debt due

from Mr. Kelly’s affiliated companies to FCC of $25,594,007. On that date FCC

wrote off as bad debts amounts due from the affiliated companies as follows:

Entity Amount

Hidden Hills Holding $3,883,567

Hidden Hills Resort 4,462,446

Lucky Bastard Records 952,393

Twin Peak Plaza 725,803

 Total 10,024,210

B. NSI Dividends of Debt

In 2007 and 2008 NSI-DE declared that the shareholders would receive

dividends of the purported debts due to NSI-DE from FSIF, Kelly Capital, Mr.

Kelly, and Mr. Spriggs. The payment of those dividends meant that FSIF, Kelly

Capital, Mr. Kelly, and Mr. Spriggs no longer owed the dividend amounts to NSIDE and NSI-CA. Instead, the debts were due to NSI-DE’s shareholders. On June

25, 2007, NSI declared a dividend of the FSIF debt of $31,131,284 (2007
- 35 -

[*35] dividend), which was allocated 95% to Kelly Capital ($29,574,307) and 5%

to Mr. Spriggs ($1,556,564). According to the 2007 dividend in kind, FSIF no

longer owed the dividend amount to NSI and instead owed it to Kelly Capital and

Mr. Spriggs.

On December 31, 2008, NSI declared a dividend of $40,197,895 (2008

dividend) that was allocated 95% to Kelly Capital and 5% to Mr. Spriggs. Kelly

Capital received a dividend of debt due from Mr. Kelly to NSI-DE of $24.5

million plus interest of $2,161,419 for a total of $26,661,419 and a debt due from

Kelly Capital of $9,703,876 plus interest for a total of $11,459,081. Mr. Spriggs

received a dividend for that amount that he had due to NSI of $1,813,747 plus

interest. According to the 2008 dividend in kind, the $26,661,419 debt was due

from Mr. Kelly to Kelly Capital and Kelly Capital no longer owed the $11,459,081

debt to NSI-DE. On its books and records NSI-DE treated the dividend of the

$11,459,081 debt due from Kelly Capital as a shareholder distribution and reduced

the amount due from Kelly Capital by $11,459,081. According to the 2008

dividend in kind, Mr. Spriggs no longer owed $1,813,747 plus interest to NSI-DE. 

During 2008 NSI-CA also transferred stock in two unrelated companies,

IMPAC and Freemont, to Kelly Investments. NSI-CA initially recorded the
- 36 -

[*36] transfer of the Freemont stock as a $1.8 million debt due from Kelly

Investments but later increased the amount to $8.1 million.

C. Separation of Brothers’ Businesses

During the 2008 recession Mr. Kelly and Richard decided to separate their

business affairs. Kelly Capital had transferred substantial amounts of money to

Richard including approximately $3.5 million in both 2007 and 2008 and an

additional $800,000 in 2009. Richard used these funds to pay personal expenses. 

As of May 2009 he had a balance due to Kelly Capital of $1,871,518 and TBE had

a balance due of $309,529. In the process of separating Mr. Kelly and Richard’s

businesses, Kelly Capital agreed to cancel these debts as part of an exchange

agreement dated May 11, 2009. The brothers also restructured their ownership

interests in various businesses that they jointly owned including JCE, TBE, and

one other entity not relevant here. They went from equal owners of JCE to Mr.

Kelly’s owning a 75% interest and Richard’s owning 25%. For TBE, of which

Mr. Kelly and Richard had owned 51% and 49%, respectively, Richard’s interest

increased to 77.6%, Mr. Kelly’s interest decreased to 18.2%, and three other

individuals received the remaining interest.
- 37 -

[*37] D. 2010 Discharge of Debt

In March 2010 Mr. Kelly disposed of his interest in Radius Mortgage. 

Sometime in late 2010 or early 2011 Mr. Kelly had a meeting with his legal, tax,

and accounting advisers, including Mr. Thomas, Mr. Bowen, and Mr. Marks, who

advised Mr. Kelly that he was insolvent. Mr. Kelly wanted to avoid bankruptcy

but found it impossible to repay third-party loans due to Fortress and Home

Savings & Loan Co. (Home Savings). On December 30, 2010, Mr. Kelly removed

Mr. Spriggs from NSI-DE’s board of directors and elected himself the sole

director. The next day, as the sole director of the board, Mr. Kelly decided to

write off debts of $63,910,310 and $14,916,596 due from Kelly Capital and Kelly

Investments, respectively. These debts were due to both NSI-DE and NSI-CA. 

For the 2010 tax year Mr. Kelly wrote off debt due to and from his affiliated

companies and claimed short-term capital losses for the discharged debt. 

On his 2010 personal return Mr. Kelly reported bad debt writeoffs of

$86,979,956 as short-term capital losses from his single-member LLCs as follows:

$72,968,676 from Kelly Capital, $9,672,301 from Kelly Investments, $4,127,750

from FSIF, $24,972 from Kelly Hospitality, and $186,257 due from Virtucon. Of

the $72,968,676 written off by Kelly Capital Mr. Kelly personally owed $25.8

million and the remainder was owed by Mr. Kelly’s affiliated companies: $2
- 38 -

[*38] million due from Greenback Entertainment, $4.7 million from Greenback

Holdings, $17.9 million from FCC, $1.5 million from Lemen Road Properties,

LLC (Lemen Road), $7.2 million from Kelly MOB1, LLC (MOB1), $2.7 million

from Virtucon, $4.3 million from KY&C, and $6.4 million from LBHorizons.

Mr. Kelly also reported $1,854,905 of short-term capital losses that had

passed through from the bad debts of NSI-DE, JCE, IHSD, FCC, and Greenback

Entertainment as set forth in more detail below. He calculated losses from the

writeoff of the total bad debts due to these five entities of approximately $91.4

million and claimed the reduced amount as a loss deduction on the basis of loss

limitations. He reduced tax attributes of these entities and carried forwarded

$57,650,995 of the losses. In total, he reported net short-term capital losses of

$88,834,861. He also reported net long-term capital gain of $7,554,255. 

NSI wrote off debt of $63,910,310 and $14,916,596 due from Kelly Capital

and Kelly Investments, respectively, and claimed a $78,826,906 short-term capital

loss for “BAD DEBT WRITE OFF” on its 2010 S corporation return. As a 95%

shareholder, Kelly Capital was allocated $74,885,561 of the loss deduction. NSI

attached a statement to its 2010 return stating that Kelly Capital and Kelly

Investments were insolvent, as follows:
- 39 -

[*39] NON-BUSINESS BAD DEBT: IN PREVIOUS YEARS

NATIONAL SERVICE INDUSTRIES, INC. * * * ADVANCED

KELLY CAPITAL, LLC * * * $63,910,310 AND KELLY

INVESTMENTS, LLC * * * $14,916,596 * * * FOR A TOTAL OF

$78,826,906. IT WAS DETERMINED THAT KELLY CAPITAL,

LLC AND KELLY CAPITAL INVESTMENTS, LLC WERE

INSOLVENT THEREFORE THIS AMOUNT WOULD NOT BE

RECOVERED AND SHOULD BE WRITTEN OFF AS

NON-BUSINESS BAD DEBT. 

FCC and IHSD also reported short-term capital losses from the writeoff of

bad debt of $5,603,393 and $12,287,799, respectively, including debt due from

Kelly Capital, Kelly Investments, and JCE. However, a substantial amount of the

debt that FCC wrote off, $4.2 million, was due from Mr. Kelly personally.

On his 2010 return Mr. Kelly reported the discharge of debt due from his

affiliated companies and attached Form 982, Reduction of Tax Attributes Due to

Discharge of Indebtedness (and Section 1082 Basis Adjustment), reporting a

discharge of indebtedness of $145,559,306 that was excluded from gross income

on the basis of his insolvency calculated as follows:

Entity Amount

Greenback Holdings $2,605,586

JCE 3,793,437

IHSD 7,052,215

FCC 4,200,407
- 40 -

Kelly Hospitality 3,027,829

KY&C 4,299,116

LBHorizons 6,418,852

Radius Mortgage 86,575

Kelly Investments 16,928,020

Lemen Road 1,561,373

MOB1 7,161,363

Kelly Capital 85,743,031

Virtucon 2,659,565

FSIF 21,937

Included in this calculation is the debt due from Kelly Capital and Kelly

Investments of approximately $63.9 million and $14.9 million, respectively, that

NSI wrote off and reported on its 2010 return. Of the above calculation of COD

income, only a small portion of the debt is unrelated to transfers from NSI. The

following debt was not related to transfers from NSI: the entire amount owed by

Kelly Hospitality and IHSD, $1,201,000 of the Lemen Road debt, and $3,793,437

of the JCE debt. Mr. Kelly also had COD income of $4,011,851 from the

discharge of debt owed to third-party lender Home Savings. On December 23,

2010, Mr. Kelly and his affiliated companies entered into an omnibus forbearance

agreement with Home Savings that discharged debt of $4,011,851. Accordingly,

[*40]
- 41 -

[*41] Mr. Kelly had COD income for 2010 unrelated to transfers from NSI of at

least $19,329,039. 

Included in the 2010 debt writeoff was $7,161,363 due from MOB1. At the

time of the writeoff MOB1 owned and leased a medical office building. The

rental activity was unprofitable during 2009 and 2010. However, after the writeoff

Mr. Kelly sold rights in three cell towers on the building’s roof for $1 million and

then sold the building in a separate transaction. 

FCC and Greenback Entertainment also filed Forms 982 attached to their

2010 returns. FCC reported COD income of $21,175,933, including $17,848,030

due to Kelly Capital, $2,127,750 due to FSIF, and the remainder due to five other

companies. On Form 982 FCC reported $20,992,619 of discharged of debt

excluded from its gross income on the basis of its insolvency. FCC claimed a

short-term capital loss deduction of $5,603,393 for the writeoff of bad debt due

from Mr. Kelly and his affiliated companies including $1,356,802 due from JCE,

$11,424 from Kelly Investments, $33,516 from Kelly Capital $4,200,407 from Mr.

Kelly, and the remaining $1,243 from two other entities not relevant here.

On its 2010 return Greenback Entertainment reported a short-term capital

loss of $563,811 from the writeoff of a bad debt from Greenback Holdings. 

Greenback Entertainment also filed a Form 982 attached to its 2010 return
- 42 -

[*42] reporting the discharge of $2,014,061 of debt due to Kelly Capital.

Greenback Entertainment reported that the discharged debt was excluded from its

gross income on the basis of its insolvency.

On its partnership return for 2010 IHSD reported short-term capital losses

for “BAD DEBT WRITE OFF” of $12,287,799 and reported COD income of

$8,640,303, which included the COD income from discharged debt owed to

Fortress. The COD income was allocated $7,052,215 to Kelly Capital and

$1,588,088 to JCE.

E. NSI-DE’s Bankruptcy

As of May 9, 2010, Kelly Capital’s books showed a debt of $500,000 due

from NSI-DE to Kelly Capital. On that date Kelly Capital purchased NSI-CA

from NSI-DE in exchange for release from the $500,000 debt. In July 2012 NSIDE filed a voluntary petition for chapter 7 bankruptcy to which NSI-DE’s board of

directors gave its unanimous written consent. Therein NSI-DE’s board of

directors stated that “it is in the best interest of the Company, its creditors, and

other interested parties to file a voluntary petition for relief”. In its bankruptcy

petition, NSI-DE reported assets of less than $300,000 and liabilities of

approximately $55 million consisting primarily of unsecured asbestos claims

which included the $35.7 million default judgment. 
- 43 -

[*43] On June 4, 2014, the bankruptcy trustee commenced an adversarial

proceeding against NSI, Kelly Capital, KCI, FSIF, NSI-CA/Englewood, Mr.

Kelly, and Mr. Spriggs. On November 23, 2015, Mr. Kelly and the other

defendants filed an answer denying the trustee’s allegations and asserting

defenses. On January 16, 2017, the parties to the bankruptcy proceeding filed a

motion to approve a compromise in accordance with a settlement agreement that

called for a $3.5 million stipulated judgment against Mr. Kelly. The motion to

approve compromise was granted on February 10, 2017.

In 2012 Mr. Kelly organized two new entities, Kelly Investment Group,

LLC, and KC Advisors, LLC. He moved all of Kelly Capital’s employees to these

new entities. In 2013 Kelly Capital’s existence terminated.

VI. Personal Life

On April 18, 2006, Mr. Kelly moved from San Diego, California, to Miami

Beach, Florida. In September 2007 he purchased the residence in Miami Beach,

Florida (Miami house), for approximately $11.2 million, making a $5 million

downpayment and obtaining a mortgage for the rest. He did not default on the

mortgage and eventually sold the house in late 2009 for approximately $9.2

million.
- 44 -

[*44] Mr. Kelly married Nicole Dahm on October 4, 2008. In August 2009 Mr.

Kelly moved back to San Diego, California, initially moving back into his condo

in San Diego, California (San Diego condo). He sold the San Diego condo on

November 8, 2011, for $3 million. In late 2009 he purchased his current home in

Rancho Santa Fe, California, for $8.92 million, obtaining a $5 million mortgage

from Bank of America and using the proceeds of his Miami house sale to pay the

remainder of the purchase price. As of December 31, 2010, Mr. Kelly also owned

a condo in Woodstock, Georgia.

VII. Return Reporting

In 2000 Mr. Kelly retained F. Laurence Scott, Jr., of Scott & Cronin, LLP

(S&C), to prepare his personal return for 1999. Mr. Scott was Mr. Kelly’s primary

contact at S&C. Mr. Scott and Jason Brustkern, also of S&C, were involved in the

preparation of Mr. Kelly’s 2007 through 2011 personal returns. Both men are

C.P.A.s with no history of adverse disciplinary actions or Internal Revenue

Service (IRS) preparer penalties.

Mr. Kelly received and reported wages from NSI of approximately $1

million per year for 2007 and 2008. He also reported a minimal amount of wages

from FCC of less than $10,000 per year for each of the years at issue. 
- 45 -

[*45] As explained above, Mr. Kelly did not cause his single-member LLCs to file

entity-level returns. Instead, he reported the tax items for the LLCs on

Schedules C attached to his personal returns. See sec. 301.7701-3(b), Proced. &

Admin. Regs. (providing that a single-member LLC is a disregarded entity). 

Accordingly, Kelly Capital, Kelly Investments, Kelly Hospitality, FSIF, Virtucon,

KY&C, Radius Mortgage, and LBHorizons did not file entity-level returns for the

years at issue, and Kelly Finance did not file entity-level returns for 2007 through

2009, the years of its existence.

Mr. Scott prepared the Schedules C for KY&C that were attached to Mr.

Kelly’s 2008 and 2009 personal returns. On April 3, 2009, Mr. Thomas sent an

email to Mr. Scott stating that

[KY&C] is a Cayman Island Entity and I am not sure what taxes and

returns have to be filed in the Cayman Islands. * * * I am not sure

what filing requirements we have in the US since this is a Cayman

Island entity and how this flows through to Michael Kelly’s personal

return but it will have to be dealt with when filing returns for 2008.

Despite this message, Form 5471 was not filed for KY&C for 2008. Attached to

Mr. Thomas’ April 3, 2009, email were several “LLC Information Sheets”, one of

which listed KY&C as a Cayman Islands entity owned 100% by Kelly Capital. 
- 46 -

[*46] VIII. The Audit

Mr Kelly’s audit began with an examination of his 2010 personal return on

or around September 17, 2012. On October 1, 2012, 14 days after the initial

contact letter, Mr. Scott and/or Mr. Brustkern contacted the revenue agent

assigned to the audit. After an exchange of voicemails to schedule a phone

conference for October 12, 2012, the revenue agent missed that phone conference

but on October 24, 2012, requested a meeting with Mr. Kelly in a telephone call

with Mr. Scott. On that same day, Mr. Scott sent a letter to the revenue agent

enclosing tax returns that the agent had requested. 

On November 20, 2012, Mr. Kelly and his representatives met with the

revenue agent at Mr. Kelly’s office. Mr. Kelly participated in the meeting and

answered the questions that the revenue agent asked. The meeting was cut short

by the revenue agent, not Mr. Kelly or his representatives. Generally, requested

records were freely provided by Mr. Kelly or Mr. Scott to the IRS. Mr. Kelly was

not summoned to meet with the IRS. 

There were between 15 and 20 voluntary meetings between IRS revenue

agents and Mr. Kelly or his representatives during the course of the examination. 

There were also at least three voluntary meetings between the IRS Office of

Appeals and Mr. Kelly’s representatives following the audit. Mr. Kelly answered
- 47 -

[*47] all the IRS’ questions at the subsequent meetings where he was present. In

short, he cooperated with the audit. He agreed to extend the periods of limitations

when the IRS asked him to do so.

Respondent issued two notices of deficiency to Mr. Kelly, the first on

December 10, 2015, for tax years 2010 and 2011, and the second on May 19,

2016, for tax years 2007, 2008, and 2009. The second notice of deficiency was

the first formal communication to Mr. Kelly of the initial determination to assess

penalties for tax years 2007, 2008, and 2009. Respondent’s initial determination

of the fraud penalty under section 6663(a) for 2007, 2008, and 2009 was

personally approved in writing by the immediate supervisor of the IRS employee

who made the initial determination, as required by section 6751(b), on October 8,

2015, a date before the mailing of the notice of deficiency for those years.

OPINION

I. Statute of Limitations

The period of limitations under section 6501 is in dispute for 2007, 2008,

and 2009. Respondent argues the filing of false or fraudulent returns with the

intent to evade tax under section 6501(c)(1). He argues that the periods of

limitations remain open under section 6501(c)(8) for 2008 and 2009 on the basis

that Mr. Kelly failed to file timely Forms 5471 to report KY&C as a controlled
- 48 -

[*48] foreign corporation as required by section 6038(a)(1) for these two years. 

Respondent also argues that the six-year rule for a substantial omission from gross

income under section 6501(c)(1) and (e) provides a separate ground to assess a

deficiency for 2009. We later hold that fraud is not sustained, so we must review

respondent’s alternative positions. Mr. Kelly acknowledges that 2009 is

potentially subject to the six-year rule of section 6501(e) for a substantial omission

from gross income. 

Mr. Kelly filed the Forms 5471 for 2008 and 2009 in 2019. Accordingly,

section 6501(c)(8) may hold open the 2008 and 2009 periods of limitations until

October 23, 2022, three years from when Mr. Kelly filed the Forms 5471. 

However, if reasonable cause for the failure to file Forms 5471 exists, then under

section 6501(c)(8)(B) only the adjustments related to KY&C would remain open

under the statute of limitations. Petitioner asserts that reasonable cause exists and

stems from the failure of Mr. Kelly’s tax return preparer, S&C, to follow through

on the information Mr. Kelly and his staff provided to it.

Section 6501(c)(8) does not define reasonable cause. Nor do the regulations

thereunder. However, it is appropriate to rely on the Supreme Court’s definition

in United States v. Boyle, 469 U.S. 241, 246 (1985), that the taxpayer must

exercise “[o]rdinary business care and prudence” (quoting section 301.6651-
- 49 -

[*49] 1(c)(1), Proced. & Admin. Regs.). We have relied on this definition for the

reasonable cause defense to the section 6038(b) penalty for a failure to furnish the

appropriate information with a return. See Flume v. Commissioner, T.C. Memo.

2017-21. Taxpayers can establish reasonable cause on the basis of their reliance

on the advice of a tax professional. Id. Such reliance requires that the taxpayer

prove: (i) the adviser was a competent professional with sufficient expertise, (ii)

the taxpayer provided necessary and accurate information to the adviser, and (iii)

the taxpayer relied in good faith on the adviser’s judgment. Neonatology Assocs.,

P.A. v. Commissioner, 115 T.C. 43, 98-99 (2000), aff’d, 299 F.3d 221 (3d Cir.

2002). The taxpayer’s education and business experience are relevant to

determine whether he reasonably and in good faith relied on a tax professional.

Sec. 1.6664-4(b)(1), Income Tax Regs. 

S&C has prepared Mr. Kelly’s personal returns since 2000, including

Schedules C for his affiliated companies. S&C prepared approximately 700 tax

returns per year. Mr. Scott was the primary contact for the preparation of Mr.

Kelly’s returns. Mr. Scott is a C.P.A. with no history of adverse disciplinary

actions or IRS preparer penalties. He had decades of experience with Federal tax

return preparation but had no prior knowledge of Form 5471 in 2009. It was

reasonable for Mr. Kelly to rely on Mr. Scott. S&C was adequately advised that
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[*50] Mr. Kelly owned a Cayman Islands entity. Mr. Kelly’s staff pointed out that

there might be a different reporting. Conversely, in Flume, the taxpayer failed to

provide his tax return preparer all the necessary information.

Respondent contends that it was not enough for Mr. Kelly to inform S&C

that KY&C was a foreign entity, and he implies that Mr. Kelly should have

advised Mr. Scott that Form 5471 was required. The failure to file the Forms 5471

does not present an obvious tax obligation which was negligently omitted from

information that a taxpayer provided to the return preparer. Mr. Kelly, through his

staff, provided the necessary information to S&C, identified KY&C as a foreign

corporation, and stated that he was unsure of the reporting requirements. Having

done this, Mr. Kelly reasonably relied on S&C to prepare his returns properly. 

While it could be argued that S&C should have done more to ascertain Mr. Kelly’s

filing obligations, it was reasonable for Mr. Kelly to rely on S&C do so. A

taxpayer need not question the advice provided, obtain a second opinion, or

monitor the advice received from the professional. Boyle, 469 U.S. at 251. 

At trial, Mr. Scott credibly described the reasons that his firm failed to

prepare Form 5471 for KY&C. No facts suggest that the failure was the result of a

conflict of interest or a “too good to be true” situation for either year. Ultimately,

Mr. Kelly’s reliance on S&C to help meet his filing obligations was reasonable
- 51 -

[*51] and done in good faith, and the periods of limitations for 2008 and 2009 do

not remain open for adjustments unrelated to KY&C under section 6501(c)(8)(A)

after the application of section 6501(c)(8)(B). In fact, respondent did not advise

Mr. Scott about the nonfiling of the Forms 5471 until 2019, three years after these

cases began. Mr. Scott prepared and filed the Forms 5471 quickly thereafter. We

hold that Mr. Scott’s lack of prior experience with Form 5471 was not fatal to a

finding of Mr. Kelly’s reasonable reliance on him or S&C.

II. Fraud

Respondent determined fraud penalties under section 6663, for which

respondent bears the burden of proof by clear and convincing evidence. See sec.

7454(a); Rule 142(b). Respondent’s burden is to prove, for each year, by clear and

convincing evidence, that (1) Mr. Kelly underpaid his tax for that year and (2)

some part of that underpayment for that year was due to fraud. See Parks v.

Commissioner, 94 T.C. 654, 660-661 (1990). 

Fraud for these purposes is defined as intentional wrongdoing with the

specific purpose of avoiding a tax believed to be owed. DiLeo v. Commissioner,

96 T.C. 858, 874 (1991), aff’d, 959 F.2d 16 (2d Cir. 1992). Stated differently,

imposition of the civil fraud penalty is appropriate upon a showing by the

Commissioner that the taxpayer intended to evade taxes believed to be owing by
- 52 -

[*52] conduct designed to conceal, mislead, or otherwise prevent the collection of

taxes. Id.; see also Petzoldt v. Commissioner, 92 T.C. 661, 698 (1989). But fraud

“does not include negligence, carelessness, misunderstanding or unintentional

understatement of income.” United States v. Pechenik, 236 F.2d 844, 846 (3d Cir.

1956). Fraud “is not proven when a court is left with only a suspicion of fraud,

and even a strong suspicion is not sufficient to establish a taxpayer’s liability for

the fraud penalty.” Branson v. Commissioner, T.C. Memo. 2012-124, slip op. at

23 (citing Olinger v. Commissioner, 234 F.2d 823, 824 (5th Cir. 1956), aff’g in

part, rev’g in part on another ground T.C. Memo. 1955-9, Davis v. Commissioner,

184 F.2d 86, 87 (10th Cir. 1950), and Green v. Commissioner, 66 T.C. 538, 550

(1976)). Moreover, even when a taxpayer “engage[s] in aggressive tax planning to

minimize his taxes”, this Court has found that such action alone is not enough to

establish the requisite fraudulent intent. Klaas v. Commissioner, T.C. Memo.

2009-90, slip op. at 33, aff’d, 624 F.3d 1271 (10th Cir. 2010). 

As direct proof of a taxpayer’s intent is seldom available, fraud has been

established by circumstantial evidence and reasonable inferences drawn from the

record. Stoltzfus v. United States, 398 F.2d 1002, 1005 (3d Cir. 1968); DiLeo v.

Commissioner, 96 T.C. at 874. Courts have thus developed a list of “badges of

fraud” useful in determining whether there is circumstantial evidence of fraudulent
- 53 -

[*53] intent. Niedringhaus v. Commissioner, 99 T.C. 202 (1992). Among the

badges of fraud that can be gathered from the caselaw of the Court of Appeals for

the Ninth Circuit, to which these cases are appealable, are the following: (1) an

understatement of income, (2) inadequate maintenance of records, (3) a failure to

file tax returns or the filing of false returns, (4) offering implausible or

inconsistent explanations of behavior, (5) concealment of income or assets, and

(6) failure to cooperate with tax authorities. Bradford v. Commissioner, 796 F.2d

303, 307-308 (9th Cir. 1986), aff’g T.C. Memo. 1984-601. Courts have also

considered: (7) engaging in illegal activities; (8) dealing in cash; (9) failing to

make estimated payments; (10) offering false or incredible testimony; and

(11) filing false documents. Niedringhaus v. Commissioner, 99 T.C. at 211; Parks

v. Commissioner, 94 T.C. at 664-665.

Additionally, the taxpayer’s background, level of education, and prior

history of filing proper returns are relevant. Niedringhaus v. Commissioner, 99

T.C. at 211. A taxpayer’s education and sophistication are not themselves badges

of fraud but are relevant factors in determining “whether a taxpayer could have

formed the intent necessary to be found liable for the fraud penalty.” Holmes v.

Commissioner, T.C. Memo. 2012-251, at *31 n.16 (quoting Wickersham v.
- 54 -

[*54] Commissioner, T.C. Memo. 1999-267, slip op. at 12), aff’d, 593 F. App’x

693 (9th Cir. 2015).

Respondent asserts the following badges of fraud:

(1) consistent understatements of tax for 2007, 2008, 2009, 2010, and

2011;

(2) concealment of income by Mr. Kelly telling his staff that the NSI 

transfers were loans even though he planned to liquidate NSI and never intended

to pay back the transfers;

(3) implausible and inconsistent statements made by Mr. Kelly, such

as his testimony that he wanted to use the funds from NSI to invest in other

business opportunities, but had spent millions of dollars of purportedly borrowed

money on personal expenses and did not give NSI any ownership interest in the

business ventures in which it was supposedly investing;

(4) providing false and misleading information to S&C about the 

transfers from NSI including false books and records that Mr. Kelly maintained for

his businesses that recorded the transfers from NSI as loans;

(5) inadequate records and false documents to reflect the terms of the 

purported loans from NSI and the filing of Federal tax returns for 2007 through

2009 that omitted substantial amounts of income; and
- 55 -

[*55] (6) a scheme that Mr. Kelly designed to defraud creditors including

the IRS, to use NSI’s assets as a piggy bank for his personal spending and to

cancel the debt, and to assert the insolvency of NSI to avoid paying tax. 

Respondent’s list depends totally on the premise that Mr. Kelly’s

intercompany transfers or withdrawals recorded as loans were not properly treated

as loans and were concealed with intent to defraud the United States. While we do

not presume the accounting by Mr. Kelly and his companies is always accurate

regarding the “loans”, we do not believe the record establishes by clear and

convincing evidence that the “loans” were the basis of a fraudulent tax scheme;

rather they were the products of two decades of Mr. Kelly’s business practices. As

we discuss later herein, we agree with respondent that by 2008 there was no

reasonable expectation the “loans” would be repaid when incurred, and they

should be treated as distributions. This conclusion does not in itself lead to a

finding of fraud.

Respondent alleges but fails to prove an intent to defraud creditors,

concealment of income or assets, fraudulent failure to file returns, and false

statements. Rather, Mr. Kelly’s companies’ accounting records revealed that the

transfers were recorded as loans as an established practice of his businesses. Mr.

Kelly had a history of juggling all the sources of cash in his various enterprises to
- 56 -

[*56] leverage opportunities. He treated the cash as available to him and before

the years at issue he used this strategy to build the portfolio of assets he controlled. 

He did not hide these transactions, and the transactions were tracked in the records

of his companies.

Mr. Kelly respected his accounting staff. He respected the separate

corporate entities and their accounting records, which recorded the transfers of

funds generally as loans. Respondent alleges that these loans were fraudulent and

that Mr. Kelly has committed tax fraud on the basis of the transfers’ characterizations as loans. Respondent’s position is in effect that Mr. Kelly had been engaged

in tax fraud since the 1990s with his practice of using intercompany loans or that

Mr. Kelly’s practice became fraudulent with the NSI acquisition. We find that

respondent has failed to establish fraudulent intent by clear and convincing

evidence on the basis of either premise. Regardless of whether the loans were

properly characterized as such for tax accounting purposes, the evidence does not

prove that the loan characterizations were made with fraudulent intent.

III. Intercompany Transfers

A key issue, if not the key issue in these cases, is whether a series of

transfers from NSI to Mr. Kelly and his entities were bona fide loans or should be

reclassified as taxable distributions. Mr. Kelly has consistently maintained that
- 57 -

[*57] they were loans, but respondent disagrees. As respondent correctly begins,

an intent to establish a debtor-creditor relationship exists if, when the transfers

were made, the debtor intended to repay the funds and the creditor intended to

enforce repayment. See, e.g., Beaver v. Commissioner, 55 T.C. 85, 91 (1970);

Fisher v. Commissioner, 54 T.C. 905, 909-910 (1970). This is also a question of

fact to be determined upon a consideration of all pertinent facts. Haber v.

Commissioner, 52 T.C. 255, 266 (1969), aff’d, 422 F.2d 198 (5th Cir. 1970).

A bona fide debt is a debt that arises from a debtor-creditor

relationship on the basis of a valid and enforceable obligation to pay a

fixed or determinable sum of money. * * * Whether an advance gives

rise to a bona fide debt for Federal tax purposes is determined from

all the facts and circumstances. * * * To constitute a bona fide debt,

at the time of the transfer there must be a real expectation of

repayment and an intent on the part of the purported creditor to secure

repayment. * * *

2590 Assocs., LLC v. Commissioner, T.C. Memo. 2019-3, at *21.

Caselaw has established objective factors to consider when answering the

question of whether a bona fide debtor-creditor relationship exists. Those factors

include: (1) whether the promise to repay is evidenced by a note or other

instrument that evidences indebtedness, (2) whether interest was charged or paid,

(3) whether a fixed schedule for repayment and a fixed maturity date were

established, (4) whether collateral was given to secure payment, (5) whether
- 58 -

[*58] repayments were made, (6) what the source of any payments was,

(7) whether the borrower had a reasonable prospect of repaying the loan and

whether the lender had sufficient funds to advance the loan, and (8) whether the

parties conducted themselves as if the transaction was a loan. Dixie Dairies Corp.

v. Commissioner, 74 T.C. 476 (1980); see also Welch v. Commissioner, 204 F.3d

1228, 1230 (9th Cir. 2000), aff’g T.C. Memo. 1998-121; Estate of Mixon v.

United States, 464 F.2d 394, 402 (5th Cir. 1972); Commissioner v. Valley Morris

Plan, 305 F.2d 610, 618 (9th Cir. 1962) (defining a loan for Federal tax purposes

as “an agreement, either expressed or implied, whereby one person advances

money to the other and the other agrees to repay it upon such terms as to time and

rate of interest, or without interest, as the parties may agree” (quoting Nat’l Bank

of Paulding v. Fid. & Cas. Co., 131 F. Supp. 121, 123 (S.D. Ohio 1954))), rev’g in

part 33 T.C. 572 (1959); Knutsen-Rowell, Inc. v. Commissioner, T.C. Memo.

2011-65. 

Critical to our analysis, as is often the case, is factor (7). By 2008 Mr. Kelly

no longer had a reasonable prospect of repaying the “loans”. Mr. Kelly argues

other factors support characterization as loans. He argues that the loans were

supported by the accrual of interest and in most cases his companies followed

formalities of documenting the transfers as loans. He also maintains that the
- 59 -

[*59] repayment was derailed only by the downturn in the economy that adversely

affected his real estate holdings and the profit potential of his numerous

transactions. We find this argument reasonable through 2007, but it loses

credibility after 2007 when Mr. Kelly was well aware the economy was turning

negative to his businesses but continued to have funds transferred from NSI with

less and less expectation of repayment.

The respect for loan formalities also wanes as the economy made repayment

all but impossible beginning in 2008. Mr. Kelly’s companies followed a practice

of careful accounting of loans with some repayments through 2007, but respect for

the loan characterization and repayments gradually disappear after 2007. 

Accordingly, we hold that all NSI transfers and other intercompany transfers are

not properly characterized as loans beginning on January 1, 2008. This holding

affects respondent’s position on whether transfers are capital distributions or

dividends and, alternatively, whether Mr. Kelly has COD income for 2010. We

hold that the transfers beginning on January 1, 2008, were shareholder

distributions under sections 301 and 1368. This holding will require

recomputations under Rule 155.
- 60 -

[*60] IV. COD Income and Bad Debt Deduction for 2010

On his 2010 personal return Mr. Kelly reported $145 million of COD

income that he excluded from his gross income on the basis of his alleged

insolvency and claimed a short-term capital loss deduction for bad debt of

$86,979,956 under section 166(a)(1), which provides for a deduction of any bona

fide debt which becomes worthless within a taxable year. Mr. Kelly made

numerous transfers between his closely held companies, and on some occasions

recorded loans were forgiven as shareholder distributions.

The COD income was based largely on intercompany loans and was not

calculated with precision to eliminate intercompany debt or to ensure that only his

personal debt was actually forgiven. Likewise, the capital loss deduction for the

bad debt was calculated using the total of the recorded intercompany debts. 

Petitioner’s brief discusses the issues as follows:

In essence, because the debt was cancelled, which was picked up and

reported by Mr. Kelly as cancellation of debt income, the other side

of the same coin was a bad debt deduction. As Mr. Brustkern

testified, it was a “zero sum”: without one you cannot have the other. 

For example, when [Kelly Capital] was not able to collect the debts

owed to it from various entities, the amount was cancelled, creating

Mr. Kelly’s Schedule D bad debt deduction. Concurrently, when the

debt owed to [Kelly Capital] was cancelled, Mr. Kelly picked up the

amount as cancellation of debt income. The zero sum nature of this

reporting is also evidenced by the fact Mr. Kelly’s bad debt deduction

was eliminated through the reduction of tax attributes and his
- 61 -

[*61] insolvency calculation. * * * In fact, S&C considered reporting

neither the bad debt deduction nor cancellation of debt income,

because the two essentially offset each other on Mr. Kelly’s 2010

return. However, as Mr. Brustkern testified * * *: “When we were

preparing the return, we wanted to make sure all -- first of all, we

were just trying to make sure we reconciled all our numbers. But we

wanted to make sure that all of those numbers made it on the return

somewhere. And so we made a decision as we were preparing the

return to show everything as far as the income and the expense,

whether it was a wash or not. So that’s why the 982 has the 145 and

then the Schedule D has the other amount that you referred to.” 

Ultimately Mr. Kelly is entitled to the offsetting bad debt deduction

as discussed herein and presented at trial.

We are unconvinced by this logic. The bad debt deduction is not a function

of the alleged COD income; rather it is debt owed to Mr. Kelly, not by him. The

“zero sum” argument ignores the need to eliminate debts between his affiliated

companies. Mr. Kelly’s companies regularly passed funds between them. He has

not proven that the COD income on the business bad debts was properly

calculated and that the debts were actually owed to him or by him. Finally, our

prior holding transforms much of the debt into distributions in earlier years which

must be eliminated.

Mr. Kelly cannot create a deduction by recording intercompany debt and

then canceling it. There must be a debt owed to Mr. Kelly that is uncollectible to

create a business bad debt. Mr. Kelly has not established such debt exists or was

worthless in 2010. The parties shall calculate the amount of COD income as part
- 62 -

[*62] of the Rule 155 computations and determine the portion that is not

attributable to NSI and intercompany transfers in accordance with our holdings

herein. As explained above, at least $19.3 million of the reported COD income

was unrelated to the intercompany transfers. Mr. Kelly has not established that the

debt owed by MOB1 became worthless in the amount claimed during 2010 as

MOB1 retained ownership of the office building and cell tower rights, which it

later sold. Mr. Kelly valued the building at $2.9 million in his insolvency

calculation.

V. Tax Value of the $43,344,123 Debt Distribution

Mr. Kelly argues that the distribution of the shareholder debt and other

distributions caused by the forgiveness of shareholder debt in 2010 should be

valued at the fair market value of the debt rather than the face value. This

argument turns on characterization of the debt as property and not as a cash

equivalent. This argument has no support in the caselaw of this Court, which has

not accepted the position. In Combrink v. Commissioner, 117 T.C. 82, 94 (2001),

we stated that cancellation of shareholder debt “is considered the equivalent of a

distribution of money in the face amount of the obligation.” In an analogous

situation, the assumption of shareholder debt under section 1001(b) is deemed

money received in the face amount of the debt. Maher v. Commissioner, 55 T.C.
- 63 -

[*63] 441, 456 (1970), aff’d in relevant part and remanded in part, 469 F.2d 225

(8th Cir. 1972).

The logical result of Mr. Kelly’s argument would be to superimpose a test

of the shareholder’s solvency upon the application of section 1.301-1(m), Income

Tax Regs., and the statutory treatment of such a distribution. We find no such

hurdle in the statute or the regulations. Accordingly, we hold that the distributions

caused by cancellation of shareholder debt are properly set at the face amounts of

the debts canceled.

VI. Claimed Insolvency

Mr. Kelly asserts that he was insolvent in 2010 and his liabilities exceeded

his assets by over $154 million. Accordingly, he asserts relief from inclusion of

COD income reflected on his 2010 personal return under section 108(a)(1)(B). 

This is a question of fact which is contested in these cases. The reported COD

income is overstated and should be recalculated on the basis of this opinion as part

of the Rule 155 computations. His proposed calculation of his liabilities for

purposes of the insolvency calculation includes some liabilities of his affiliated

companies which should be eliminated and some alleged debt which will be

treated as distributions on the basis of our prior holding. Debts due from Kelly

Capital and Kelly Investments are not properly included in the insolvency
- 64 -

[*64] calculation. Mr. Kelly inappropriately included $36,888,254 in secondary

intercompany loans. 

Respondent’s insolvency calculation reflects liabilities of $88,460,849,

which removed the NSI and intercompany debt. We find this calculation

conforms more closely to the record. It should be used as the starting point for the

computations under Rule 155 of Mr. Kelly’s insolvency in 2010. Net of any debt

treated as distributions on the basis of our holding herein, we adopt this figure for

the necessary Rule 155 computations to determine whether there is any COD

income excluded from gross income for 2010. 

Respondent also argues that third-party debt owed by KY&C and personally

guaranteed by Mr. Kelly should be removed from his liabilities. Such debt is

appropriate to consider as liability of Mr. Kelly where it is “more probable than

not that he will be called upon to pay that obligation in the amount claimed”. 

Merkel v. Commissioner, 109 T.C. 463, 484 (1997) (establishing a liability on the

basis of a personal guaranty), aff’d, 192 F.3d 844 (9th Cir. 1999). Mr. Kelly

personally entered into the loan agreements for the third-party debt together with

his two wholly owned LLCs, Kelly Capital and KY&C. The debt was eventually

paid in full. We find that Mr. Kelly has established that as of 2010 he would be

required to pay the liability. Likewise, he remained liable for the remaining $8.8
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[*65] million loan balance on the basis of his personal guaranty after Virtucon

surrendered the airplane in partial satisfaction of the bank debt and satisfied the

Merkel standard for this liability.

Mr. Kelly has also established his liability for IHSD’s $62 million

construction loan. Respondent suggests on brief that the debt should not be 

treated as a liability of Mr. Kelly because of the Andaz Hotel’s agreement to make

payments on the debt for a limited time. However, respondent’s insolvency

calculation on brief includes $50 million of the construction loan as a liability of

Mr. Kelly, which we treat as a concession by respondent. Furthermore, we find

that the debt is a liability of Mr. Kelly under the Merkel standard. We dismiss

respondent’s objections to other liabilities listed in Mr. Kelly’s insolvency

calculation including his credit card debt. 

Respondent also challenges Mr. Kelly’s calculation of his assets,

approximately $70 million. Respondent challenges the value that he assigned to

his cars, his personal residences, Gaslamp Partners, his ownership interest in

IHSD, and KY&C’s yacht. We find that Mr. Kelly has established the values

placed on these assets except for the yacht. Respondent placed a value of $5

million on the yacht, which we find better reflects its fair market value in the light
- 66 -

[*66] of the purchase offers that KY&C received for the yacht in late 2010 and

early 2011 of $5.3 million to $8 million. 

Respondent alleges that Mr. Kelly omitted his ownership of Virtucon’s

airplane, a $680,537 tax refund, and his ownership interests in 14 affiliated

companies including one purportedly holding tobacco escrows. We find that the

tax refund is properly included as an asset for purposes of the insolvency

calculation. Virtucon surrendered the airplane during 2010. Accordingly, it is not

an asset for purposes of the insolvency calculation. The record establishes that

Mr. Kelly properly identified the affiliated companies that continued to have any

value as of December 31, 2010, for purposes of his insolvency calculation and did

not omit any entities as alleged by respondent. Those entities had no, or minimal,

gross receipts or business activity. The record establishes that any omitted entities

had no value. Further, the record supports the values for the following assets as

set forth in Mr. Kelly’s original or revised insolvency calculations: $41,697,709

for his IHSD investment, $2,025,000 for Gaslamp Partners, $950,000 for Kelly

Fernley, LLC, and $2,880,000 for MOB1.

Respondent asserts that the value of Mr. Kelly’s personal assets of

approximately $2.6 million listed in his insolvency calculation should be doubled

to include Mrs. Kelly’s share of the assets on the basis of community property law. 
- 67 -

[*67] Mr. Kelly objects to this adjustment on the basis of his prenuptial

agreement. He argues that there is no community property. Respondent’s

argument is premised on an allegation that Mr. Kelly did not list all of his personal

property in his statement of assets. Mr. Kelly failed to provide an itemized list of

his personal property and thus cannot support the value that he assigned to his

assets irrespective of community property laws. See Bressi v. Commissioner, T.C.

Memo. 1991-651, aff’d, 989 F.2d 486 (3d Cir. 1993). Accordingly, we accept the

value asserted by respondent of approximately $5.2 million. 

Respondent also argues that Mr. Kelly has not established that FCC and

Greenback Entertainment were insolvent as of December 31, 2010. Mr. Kelly did

not address either company’s insolvency on brief and has failed to establish that

they were insolvent. FCC and Greenback Entertainment reported COD income

from the discharge of intercompany debt. The reported amount of each entity’s

COD income must be calculated in the Rule 155 computations on the basis of our

holdings herein. Any amount of COD income so determined does not qualify for

exclusion from gross income under section 108(a). 

VII. Bad Debt Due From Richard

In 2009 Mr. Kelly and his brother Richard separated their business

operations. To accomplish the separation, Mr. Kelly transferred a portion of
- 68 -

[*68] ownership interest in TBE to Richard, and Kelly Capital released Richard

from liability for a loan of $1,871,518 that Richard owed to Kelly Capital. Kelly

Capital’s books reflected $309,529 due from TBE. As part of the 2009 exchange

Kelly Capital claimed a bad debt deduction of $2,667,153, which Mr. Kelly asserts

includes the $1,871,518 debt due from Richard and the $309,529 debt due from

TBE which flowed through to Mr. Kelly’s personal return for 2009 as a bad debt

deduction. Mr. Kelly has conceded $721,668 of the deduction.

The factual issues associated with the deduction are whether the original

debt was worthless, whether there was consideration provided by Richard for the

debt forgiveness, and whether it was a gift from Mr. Kelly together with the TBE

stock. Mr. Kelly has not proven that the answers to these questions support the

deduction, and we do not sustain the claimed bad debt deduction.

VIII. Virtucon Interest Deduction for 2010 

For 2010 Virtucon deducted an interest expense of $1,656,597 associated

with the surrender of possession of an airplane to Bank of America. Upon

surrender, the aircraft was valued at $7.5 million for purposes of settling

Virtucon’s debt to Bank of America. Mr. Kelly contends that some portion of this

amount went to pay interest by reference to a provision in the Bank of America

loan documents that required payments to be applied to interest and late fees
- 69 -

[*69] before principal. Mr. Kelly has not established that the airplane’s surrender

would qualify as a loan payment or that he made any payment of interest. 

Accordingly, this deduction is disallowed.

IX. Yacht Expenses

KY&C owned a yacht which was the subject of debt to Wells Fargo and a

protective agreement under which Wells Fargo incurred $299,388 in expenses in

2011. Mr. Kelly reimbursed Wells Fargo for this expense, and the deduction of

this expense is sustained. Various other expenses are in dispute, and on the basis

of the trial record we sustain the expenses deducted with the exception of $21,844

of car and truck expenses for 2010 and $27,874 of depreciation for 2011.

X. LBHorizons Expenses

For 2010 respondent disallowed cost of goods sold of $5,004,200 and other

expenses related to LBHorizons’ condo project. He concedes that Mr. Kelly is

entitled to the $5,004,200 adjustment for the cost of goods sold. On the basis of

the record, we find that Mr. Kelly has proven that the other expense deductions at

issue were properly reflected on his 2010 personal return.

XI. Passive Activity Loss

Mr. Kelly deducted cumulative passive losses related to FSIF and Radius

Mortgage for 2010. He asserts that FSIF was abandoned in 2010. We find that
- 70 -

[*70] Mr. Kelly has established the amount of the loss claimed attributable to FCC

and is entitled to deduct the loss. However, the record supports a finding that FCC

had activity into 2011, and we allow the loss for that year. Respondent argues that

Mr. Kelly has not established his basis in Radius Mortgage or the amount at risk

therein or that the loss was incurred in the normal course of business. On the basis

of the record Mr. Kelly has established that he is entitled to the carryover loss, and

the deduction is sustained to the extent allowable in the Rule 155 computations.

XII. Bank Deposit Analyses 

For 2010 and 2011 respondent performed analyses of bank deposits into

Kelly Capital’s accounts and determined that Kelly Capital had unreported gross

receipts for both years. We agree with Mr. Kelly that these unreported income

adjustments duplicate respondent’s basic position that loans that flowed from

Kelly Capital to Mr. Kelly were distributions. We have sustained respondent on

the distribution adjustments for 2010 and 2011 and find that respondent has failed

to establish, to the extent he has not otherwise conceded, that the bank deposit

analyses do not duplicate the distribution adjustments.

In reaching our holdings, we have considered all arguments made, and, to

the extent not mentioned above, we conclude they are moot, irrelevant, or without

merit.
- 71 -

[*71] To reflect the foregoing,

Decisions will be entered under

Rule 155.