Court Opinion

ID: 2676288
Source: CourtListenerOpinion
Date Created: 2014-05-29 20:00:53.223211+00
Date Added: 2024-06-11T12:38:33.497060
License: Public Domain

142 T.C. No. 19

                        UNITED STATES TAX COURT

  JULIA R. SWORDS TRUST, TRANSFEREE, MARGARET R. MACKELL,
  DOROTHY R. BROTHERTON, AND JULIA R. SWORDS, CO-TRUSTEES,
                      ET AL.,1 Petitioners v.
        COMMISSIONER OF INTERNAL REVENUE, Respondent

      Docket Nos. 10882-10, 10883-10,            Filed May 29, 2014.
                  10884-10, 10885-10.

             R issued notices of transferee liability to Ps to collect D’s
      unpaid Federal income tax pursuant to I.R.C. sec. 6901. R argues that
      the following two-step analysis applies in determining whether Ps are
      liable for D’s unpaid tax: (1) analyze whether the subject transactions
      are recast under Federal law, here primarily the Federal substance

      1
       Cases of the following petitioners are consolidated herewith: David P.
Reynolds Trust, Transferee, Margaret R. Mackell, Dorothy R. Brotherton, and
Julia R. Swords, Co-Trustees, docket No. 10883-10; Margaret R. Mackell Trust,
Transferee, Margaret R. Mackell, Dorothy R. Brotherton, and Julia R. Swords, Co-
Trustees, docket No. 10884-10; and Dorothy R. Brotherton Trust, Transferee,
Margaret R. Mackell, Dorothy R. Brotherton, and Julia R. Swords, Co-Trustees,
docket No. 10885-10.
                                        -2-

      over form doctrine, and then (2) apply State law to the transactions as
      recast under Federal law.

             Held: I.R.C. sec. 6901 requires that the Court apply State
      (rather than Federal) law to determine whether a transaction is recast
      under a substance over form (or similar) doctrine.

             Held, further, R has failed to establish that an independent
      basis exists under applicable State law or State equity principles for
      holding Ps liable for D’s unpaid tax.

      Timothy L. Jacobs and William Lee S. Rowe, for petitioners.

      Randall L. Eager, Jr., Timothy B. Heavner, Matthew S. Reddington, James

R. Rich, Kristina L. Rico, and Johnny C. Young, for respondent.

      MARVEL, Judge: These consolidated cases concern separate notices of

liability that respondent issued to the cotrustees of the Julia R. Swords Trust

(Swords Trust), the David P. Reynolds Trust (Reynolds Trust), the Margaret R.

Mackell Trust (Mackell Trust), and the Dorothy R. Brotherton Trust (Brotherton

Trust) (collectively, petitioner trusts).2 Respondent determined in the notices that

petitioner trusts are liable as transferees for Davreyn Corp.’s (Davreyn) Federal

      2
      The cotrustees of each of these trusts are Margaret R. Mackell, Dorothy R.
Brotherton, and Julia R. Swords.
                                           -3-

income tax deficiency of $4,602,986,3 additions to tax under section 6651(a)(1)

and (2)4 of $1,160,137 and $1,982, respectively, an accuracy-related penalty under

section 6662 of $920,597, fees of $50, and related interest for Davreyn’s taxable

year ended (TYE) February 15, 2001. The amount of each petitioner trust’s

transferee liability as calculated by respondent is as follows: Swords Trust--

$3,833,988, Reynolds Trust--$2,710,241, Mackell Trust--$3,833,988, and

Brotherton Trust--$3,833,988. These calculated liabilities stem primarily from

respondent’s determination recharacterizing petitioner trusts’ February 15, 2001,

sales5 of their Davreyn stock as a sale of assets by Davreyn followed by Davreyn’s

distribution of its assets to petitioner trusts in liquidation.

       The sole issue for decision is whether petitioner trusts are liable as

transferees under section 6901 for Davreyn’s unpaid Federal income tax liability

       3
           Some monetary amounts have been rounded to the nearest dollar.
      4
       Unless otherwise indicated, section references are to the applicable
versions of the Internal Revenue Code, as amended, and Rule references are to the
Tax Court Rules of Practice and Procedure.
      5
       Our use in the findings of fact of “sale”, “purchase”, and similar words
generally is for convenience and is not intended to, and does not, constitute a
finding that the referenced transactions were valid transactions recognized for
Federal income tax purposes.
                                        -4-

for Davreyn’s TYE February 15, 2001. We hold that petitioner trusts are not

liable as transferees under section 6901.

                               FINDINGS OF FACT

      Some facts have been stipulated and are so found. The stipulations of fact

and the facts drawn from stipulated exhibits are incorporated herein by this

reference. When the petitions were filed, each petitioner trust had a mailing

address in Virginia. Also at that time, Ms. Mackell and Ms. Brotherton resided in

Virginia, and Ms. Swords resided in Kentucky.

I.    The Reynolds Family and Petitioner Trusts

      In 1919 Richard S. Reynolds, Sr., founded the Reynolds Metal Co.

(Reynolds Metal). Reynolds Metal produced the popular aluminum foil brand,

Reynolds Wrap. Headquartered in Richmond, Virginia, Reynolds Metal was, at

one time, the third largest aluminum company in the world.

      David Parham Reynolds (Mr. Reynolds), who died on August 29, 2011, was

the son of Richard S. Reynolds, Sr., and the sole beneficiary of the Reynolds

Trust. The Reynolds Trust was established by an instrument of indenture dated

May 14, 1932.

      Mr. Reynolds’ only children are his daughters: Ms. Swords, Ms. Mackell,

and Ms. Brotherton. Ms. Swords and her descendants are the sole beneficiaries of
                                        -5-

the Swords Trust. Ms. Mackell and her descendants are the sole beneficiaries of

the Mackell Trust. Ms. Brotherton and her descendants are the sole beneficiaries

of the Brotherton Trust. The Swords Trust, the Mackell Trust, and the Brotherton

Trust were established by separate instruments of indenture dated February 22,

1957.

        When Mr. Reynolds became ill in the late 1990s, Ms. Swords, Ms. Mackell,

and Ms. Brotherton became primarily responsible for managing petitioner trusts.

They served as cotrustees for petitioner trusts at all relevant times. Robert H.

Griffin, a certified public accountant (C.P.A.) and a partner at the Virginia

accounting firm of Mitchell Wiggins & Co., LLP (Mitchell Wiggins), has

provided accounting and tax services to petitioner trusts for decades.

II.     Davreyn

        In 1961 Davreyn was established and began business as a Virginia

corporation. At all relevant times Davreyn was a personal holding company

(PHC). Each petitioner trust received a substantial number of Davreyn shares at

the time of Davreyn’s formation.

        Before June 2000 Davreyn held a substantial number of shares in Reynolds

Metal. In June 2000 Reynolds Metal merged with Alcoa, Inc. (Alcoa), another
                                        -6-

American aluminum company, and Davreyn’s existing Reynolds Metal shares

were converted into Alcoa shares.

      As of February 1, 2001, Davreyn had assets as follows: (1) 409,830 shares

of Alcoa stock and (2) an investment in the Goldman Sachs 1999 Exchange Place

Fund (Goldman Sachs fund). The value of the Alcoa stock held by Davreyn

exceeded $14 million as of February 2001.

      As of February 14, 2001, the Swords Trust, the Mackell Trust, and the

Brotherton Trust owned all of Davreyn’s common stock. Each trust owned 1,656

of the 4,968 issued and outstanding shares of Davreyn’s common stock. The

Reynolds Trust owned all of the 35,428 issued and outstanding shares of

Davreyn’s preferred stock.

      Also as of February 14, 2001, Davreyn had officers and directors as follows:

(1) Ms. Mackell, who served as president, treasurer, and director, (2) Ms. Swords,

who served as vice president and director, (3) Ms. Brotherton, who served as vice

president and director, and (4) Mr. Griffin, who served as secretary and director.

Mr. Griffin also served as an accountant and adviser to Davreyn, and he prepared

its Federal income tax returns for its taxable years before the year in issue. Before

the transactions at issue, neither Ms. Swords, Ms. Mackell, nor Ms. Brotherton
                                        -7-

made any change to Davreyn’s operation, except for diversifying Davreyn’s

holdings by investing in the Goldman Sachs fund.

III.   Petitioner Trusts’ Sales of Davreyn Stock

       A.    Initial Meetings and Negotiations

       In the late 1990s BDO Seidman, an accounting firm, advised its local

offices about an opportunity for PHC shareholders to sell their appreciated PHC

stock to a financial buyer in a tax efficient manner. Jon Glazman, a C.P.A. with

BDO Seidman, contacted several attorneys, including Tom Word, an attorney at

McGuireWoods LLP (McGuireWoods), to inform them of this opportunity. Mr.

Word relayed this opportunity to other McGuireWoods attorneys, including

Thomas Rohman, a tax partner. Mr. Rohman later contacted Mr. Glazman about a

potential sale of PHC stock by clients of Mr. Rohman. Mr. Glazman put Mr.

Rohman in touch with Maurice Gottlieb, another C.P.A. at BDO Seidman who

specialized in PHC stock sale transactions. Eventually, Mr. Rohman and Mr.

Glazman began working together to sell PHC stock to financial buyers. As of the

beginning of February 2000 Mr. Gottlieb had structured several transactions

similar to the one at issue with the assistance of Mr. Rohman.

       Mr. Rohman at some point contacted Mr. Griffin and advised him of the

opportunity for shareholders to sell their PHC stock to a financial buyer.
                                       -8-

Although neither Mr. Griffin nor petitioner trusts were marketing or seeking to

market Davreyn, Mr. Griffin recognized that Davreyn was a candidate for this

opportunity because Davreyn was a PHC that held highly appreciated stock. On

or before February 10, 2000, Mr. Griffin mentioned to Mr. Rohman that Davreyn

was such a possible candidate, and Mr. Rohman relayed that information to Mr.

Gottlieb.

      On February 10, 2000, at Mr. Gottlieb’s request, Mr. Rohman sent to Mr.

Gottlieb and Mr. Glazman an email providing more detailed information about a

potential sale of Davreyn’s stock, including information about Davreyn’s tax basis

in its assets. In the email Mr. Rohman indicated that Davreyn held two assets, the

total market value of which was $15,526,639. These assets were: (1) 193,317

shares of Reynolds Metal common stock, with a market value of $14,498,775, and

(2) the Goldman Sachs fund shares, with a market value of $1,027,864.

      On March 7, 2000, Mr. Rohman and Mr. Griffin again discussed a potential

sale of Davreyn’s stock.6 Nine days later, a meeting was held between Ms.

      6
       Mr. Griffin testified that this discussion was the first time he knew that
there was a buyer interested in purchasing Davreyn stock. However, Mr. Rohman
sent the February 10, 2000, email to Mr. Gottlieb and Mr. Glazman containing
detailed information about Davreyn. We therefore reject the referenced testimony
and find that Mr. Rohman and Mr. Griffin discussed the sale of Davreyn stock on
or before February 10, 2000.
                                        -9-

Mackell, Ms. Brotherton, Mr. Rohman, Mr. Griffin, and Lizzie Amos, a manager

at Mitchell Wiggins. At the meeting Mr. Griffin and Ms. Amos advised Ms.

Mackell and Ms. Brotherton that petitioner trusts had five options with respect to

Davreyn: (1) continue Davreyn, (2) liquidate Davreyn, (3) sell Davreyn’s stock

for 90% of the fair market value (FMV) of its assets, (4) sell Davreyn’s stock for

the sum of 90% of the FMV of the Reynolds Metal stock plus 25% of the FMV of

the Goldman Sachs fund shares, or (5) sell Davreyn’s stock for 90% of the FMV

of the Reynolds Metal stock and distribute the Goldman Sachs fund shares to a

limited liability company (LLC). Mr. Griffin advised Ms. Mackell and Ms.

Brotherton regarding the potential sale price, as well as the mechanics and tax

consequences of a potential sale of Davreyn’s stock.

      Because of the merger between Reynolds Metal and Alcoa, any plans

regarding the sale of Davreyn’s stock were put on hold. After the merger, in

September 2000, Mr. Rohman again met with Mr. Griffin, Ms. Mackell, and Ms.

Brotherton to discuss the potential sale of Davreyn’s stock to a financial buyer. At

the meeting Mr. Rohman did not discuss the buyer’s plans with respect to either

Davreyn or Davreyn’s assets.

      Following the meeting, on September 8, 2000, Mr. Rohman sent to Ms.

Swords, Ms. Mackell, and Ms. Brotherton a memorandum reiterating his
                                        - 10 -

presentation and outlining the proposed sale transaction. In the memorandum Mr.

Rohman advised that, because of the financial buyer’s “peculiar” tax situation, a

sale of Davreyn’s stock to the financial buyer would be an attractive option for

petitioner trusts. Mr. Rohman also stated that the financial buyer would not be

interested in purchasing Davreyn if it held any assets other than the Alcoa stock.7

To account for the existence of the other asset, namely, the Goldman Sachs fund

shares, Mr. Rohman proposed that the transaction proceed as follows: (1)

Davreyn organizes an LLC, (2) Davreyn transfers the Goldman Sachs fund shares

to the LLC, (3) Davreyn distributes to petitioner trusts the ownership interests in

the LLC in exchange for some of their Davreyn shares, and (4) petitioner trusts

sell their Davreyn stock to the financial buyer for cash. Mr. Rohman advised that

the purchase price for the Davreyn stock would equal: (1) 90% of the FMV of the

Alcoa stock, (2) 100% of all the accrued dividends on the Alcoa stock, and (3)

100% of Davreyn’s cash on hand at closing, “less the amount of the estimated

corporate income tax incurred by it on the distribution” of the Goldman Sachs

fund shares to the LLC.

      7
       Mr. Rohman calculated Davreyn’s assets as follows: (1) Alcoa stock, with
an estimated tax basis of $1 million and an estimated value of $13,857,000 and (2)
Goldman Sachs fund shares, with an estimated tax basis of $167,000 and an
estimated value of $860,000.
                                        - 11 -

         With respect to the tax consequences, Mr. Rohman advised that petitioner

trusts would recognize long-term capital gain in amounts equal to the difference

between the total stock sale price and petitioner trusts’ tax bases in their Davreyn

stock. He further advised that after the transaction, petitioner trusts would own

100% of the LLC and that the LLC would have a tax basis in the Goldman Sachs

fund shares equal to their FMV. Mr. Rohman noted that Davreyn would recognize

taxable gain equal to the difference between its tax basis and the FMV of the

Goldman Sachs fund shares and that “[t]he burden of this corporate income tax

liability would effectively fall on the shareholders because the Buyer would

reduce the Purchase Price by the amount of this corporate income tax liability.”

Mr. Rohman concluded that petitioner trusts would recognize long-term capital

gain of $13,031,000 and pay tax of $3,356,000 with respect to the proposed stock

sale.8

         Although Ms. Swords, Ms. Mackell, and Ms. Brotherton had not previously

considered selling petitioner trusts’ shares in Davreyn, arranging a sale of

Davreyn’s assets, or liquidating Davreyn, they agreed on the advice of Mr. Griffin

and Mr. Rohman to sell petitioner trusts’ Davreyn stock to the financial buyer.

         8
       Mr. Rohman calculated petitioner trusts’ tax liabilities assuming a 20%
Federal income tax rate and a 5.75% State income tax rate.
                                        - 12 -

Neither Mr. Griffin, Ms. Swords, Ms. Mackell, nor Ms. Brotherton were aware of

the buyer’s identity or the buyer’s plan with respect to Davreyn or the Alcoa stock

Davreyn owned. The buyer was not acting as the agent of petitioner trusts, and

Ms. Swords, Ms. Mackell, and Ms. Brotherton were not aware of any plan by the

financial buyer to cause Davreyn or any other taxpayer to illegitimately avoid the

payment of tax. Mr. Griffin subsequently contacted Mr. Rohman to advise him

that petitioner trusts wanted to sell their Davreyn stock to the financial buyer.

      On September 13, 2000, Mr. Rohman sent an email to the chief financial

officer (CFO) of Integrated Capital Associates (ICA),9 Howard B. Teig,10

regarding the proposed stock sale transaction. In the email Mr. Rohman described

Davreyn and indicated that Davreyn would transfer the Goldman Sachs fund

shares to an LLC before the proposed stock sale. After exchanging a series of

      9
       ICA was an investment banking firm incorporated under Delaware law and
based in New York City and San Francisco. ICA had a number of affiliates,
including Integrated Acquisition Group, LLC (IAG), and ICA Fund Manager, Inc.
(ICA Fund Manager). In addition to his role as CFO of ICA Fund Manager, Mr.
Teig served as CFO of IAG and ICA Fund Manager.
      10
         Mr. Teig, a C.P.A., performed all of ICA’s accounting work, including the
preparation of its tax returns. With respect to financial transactions between ICA
and a third party, Mr. Teig performed due diligence and worked with the third
parties and outside counsel to finalize the transactions.
                                       - 13 -

emails, on September 15, 2000, Mr. Teig sent to Mr. Rohman an email with an

attached draft letter of intent.

       B.     Formation of Davreyn LLC

       On September 15, 2000, Mr. Rohman caused Davreyn LLC to be formed.

At formation Davreyn was the sole member of Davreyn LLC. Ms. Mackell and

Ms. Brotherton were the initial managers of Davreyn LLC.

       C.     Letter of Intent and Stock Purchase Agreement

       On December 14, 2000, Mr. Rohman emailed Mr. Teig to inform him that

the officers and directors of Davreyn had agreed to the proposed stock sale. After

exchanging emails Mr. Rohman sent to Mr. Teig an email with an attached draft

letter of intent.

       On January 19, 2001, ICA sent a letter of intent to Davreyn. The letter of

intent proposed a purchase price equal to: (1) 90% of the FMV of Davreyn’s

marketable securities plus (2) 100% of Davreyn’s cash and accrued dividend and

interest income. The letter provided that petitioner trusts would permit ICA to

conduct a full due diligence review of Davreyn before closing. The letter also

provided that the buyer would obtain sufficient acquisition financing. Mr. Teig

signed the letter of intent as CFO of ICA. Ms. Swords, Ms. Mackell, and Ms.
                                        - 14 -

Brotherton executed the letter of intent on behalf of petitioner trusts and returned

the executed letter of intent to ICA on January 26, 2001.

      On January 22, 2001, Mr. Rohman sent to Mr. Teig an initial draft of the

Stock Purchase and Redemption Agreement (stock purchase agreement). With

respect to the tax consequences of the transaction, the stock purchase agreement

provided that, among other things: (1) the purchase price payable on the closing

date would be reduced by an amount equal to the net interim tax liability,11 (2) the

buyer would prepare and file any returns on behalf of Davreyn and pay the related

tax for any taxable periods beginning before the closing date and ending after the

closing date, (3) the buyer would not cause Davreyn to become a member of a

consolidated group for tax purposes after the closing,12 and (4) the redemption

transaction would qualify as a redemption treated as an exchange pursuant to

      11
         The stock purchase agreement provided that the net interim tax liability
would be equal to the difference between the quarterly tax estimate and the interim
tax liability. The quarterly tax estimate would be equal to Davreyn’s estimated tax
payments for the period beginning January 1, 2001, and ended April 15, 2001.
The interim tax liability would be equal to Davreyn’s estimated Federal and State
tax liability for the period beginning January 1, 2001, and ended on the closing
date. In the closing statement Mitchell Wiggens calculated the interim tax liability
as $49,800.
      12
       The stock purchase agreement also provided that after the closing the
buyer would file articles of amendment with the Virginia State Corporation
Commission to change Davreyn’s name.
                                       - 15 -

section 302(b)(3). While the stock purchase agreement indicated that the buyer

was a statutory trust, the stock purchase agreement did not identify the buyer by

name.

        On February 6, 2001, Dan L. Rosenbaum13 emailed Mr. Rohman and Mr.

Teig an edited copy of the stock purchase agreement. In the edited stock purchase

agreement, Mr. Rosenbaum changed the purchaser’s name to Alrey Statutory Trust

(Alrey Trust). Alrey Trust14 was a Connecticut statutory trust established by First

Union and Alrey LLC.15

        13
       Mr. Rosenbaum was an attorney at the law firm of Sonnenschein, Nath &
Rosenthal LLP (Sonnenschein).
        14
         On February 7, 2001, Alrey LLC and First Union National Bank (First
Union) entered into a trust agreement to establish Alrey Trust. Mr. Teig, acting as
CFO of ICA Fund Manager (at the time, the manager of Alrey LLC), signed the
trust agreement on behalf of Alrey LLC, the trustor. W. Jeffrey Kramer, acting as
vice president of First Union, signed the trust agreement on behalf of First Union,
the trustee. Alrey Trust was terminated on June 16, 2003.
        15
         Alrey LLC, a Delaware limited liability company, was formed on February
6, 2001. Mr. Rosenbaum acted as incorporator for Alrey LLC. At the time of
formation IAG was the sole member of Alrey LLC. ICA Fund Manager was the
initial manager of Alrey LLC. At all relevant times Alrey LLC was treated as a
disregarded entity for Federal income tax purposes pursuant to sec. 301.7701-
2(c)(2)(i), Proced. & Admin. Regs.
                                       - 16 -

      D.    Davreyn’s Closing Preparations

      Mr. Teig requested that Mr. Rohman instruct Davreyn to: (1) open an

account at DB Alex. Brown, LLC, a subsidiary of Deutsche Bank AG

(collectively, Deutsche Bank) and (2) transfer its Alcoa stock to Davreyn’s newly

opened Deutsche Bank account. Accordingly, on February 9, 2001, Ms. Mackell

and Ms. Brotherton executed an account agreement to open a brokerage account

with Deutsche Bank on behalf of Davreyn. On February 13, 2001, Davreyn

transferred its Alcoa stock to its Deutsche Bank account.

      E.    IAG’s Transfer of Alrey Trust

      On February 13, 2001, in exchange for $525,000, IAG assigned to Alrey

Acquisition Corp. (Alrey Acquisition)16 its 100% membership interest in Alrey

LLC, the trustor of Alrey Trust. Following the transfer Mr. Austin was appointed

as the manager of Alrey LLC. Accordingly, as of February 13, 2001, Alrey LLC

was owned outright by Alrey Acquisition, which had only one shareholder, Sunny

Capital. Furthermore, as of February 13, 2001, Mr. Austin was the manager of

      16
        Alrey Acquisition, a Delaware corporation, was formed on February 6,
2001. Mr. Rosenbaum acted as incorporator for Alrey Acquisition. On February
6, 2001, Mr. Rosenbaum, acting on behalf of Alrey Acquisition, adopted a
resolution electing Larry J. Austin as the sole director of Alrey Acquisition.
Sunny Capital Assets 1999 Trust (Sunny Capital) was the sole shareholder of
Alrey Acquisition. Mr. Austin was the trustee of Sunny Capital.
                                         - 17 -

Alrey LLC and the sole director, president, secretary, and treasurer of Alrey

Acquisition.

      F.       Alrey Trust’s Financing

      Integrated Holdings Ltd. (Integrated Holdings), a company in the Cayman

Islands,17 provided financing, via a loan and a promissory note, for Alrey Trust’s

acquisition of Davreyn’s stock. On February 14, 2001, $16 million was deposited

into Alrey Trust’s account at First Union, presumably by Integrated Holdings.

      G.       The Redemption Transaction

      On February 15, 2001, Davreyn transferred the Goldman Sachs fund shares

to Davreyn LLC in exchange for a 100% membership interest in Davreyn LLC.

Davreyn then redeemed 1 share of its issued and outstanding common stock from

each of the Swords Trust, the Mackell Trust, and the Brotherton Trust in exchange

for the distribution of one-third of its membership interest in Davreyn LLC to each

of those trusts. Following the redemption transaction the Swords Trust, the

Mackell Trust, and the Brotherton Trust each owned 1,655 shares of Davreyn

common stock and a one-third membership interest in Davreyn LLC.

      17
         ICA and First Union planned to use Integrated Holdings as a financier for
the Davreyn stock sale transaction as early as February 7, 2001. Mr. Teig testified
that Integrated Holdings was a third party unrelated to ICA. However, he later
testified that ICA often established entities that began with the word “integrated”
and admitted that it was possible that ICA established Integrated Holdings.
                                       - 18 -

      H.     The Stock Sale Transaction

      Davreyn, petitioner trusts, and Alrey Trust entered into the stock purchase

agreement on February 15, 2001. Ms. Mackell executed the stock purchase

agreement on behalf of Davreyn, Ms. Swords, Ms. Mackell, and Ms. Brotherton

executed the stock purchase agreement on behalf of petitioner trusts, and Mr.

Kramer executed the stock purchase agreement on behalf of Alrey Trust.

      Pursuant to the stock purchase agreement, on February 15, 2001, the Swords

Trust, the Mackell Trust, and the Brotherton Trust each sold 1,655 shares of

Davreyn common stock and the Reynolds Trust sold all of its shares of Davreyn

preferred stock to Alrey Trust. In exchange Alrey Trust transferred $13,102,055

in cash to an escrow account held by McGuireWoods.18 On that same date the

cash proceeds were wired from the McGuireWoods escrow account to petitioner

trusts’ accounts at Merrill Lynch as follows: Reynolds Trust--$2,673,431, Swords

Trust--$3,416,891, Mackell Trust--$3,416,891, Brotherton Trust--$3,416,891. A

portion of the cash proceeds was used to pay petitioner trusts’ representatives;

      18
        According to the closing statement the $13,102,055 equaled (1) 90% of
the $14,544,867 FMV of Davreyn’s Alcoa stock as determined on the basis of
Alcoa’s closing price on February 14, 2001, plus (2) $61,475 of accrued
dividends, less (3) a $49,800 interim tax liability as computed by Mitchell
Wiggins.
                                       - 19 -

McGuireWoods and Mitchell Wiggins received payments of $139,500 and

$38,450, respectively.

      Mr. Griffin and Ms. Swords, Ms. Mackell, and Ms. Brotherton then

resigned from their positions as the officers and directors of Davreyn, effective

February 15, 2001. By letter dated February 15, 2001, Ms. Mackell released her

authority over Davreyn’s Deutsche Bank account.

IV.   Alrey Trust’s Pre- and Post-Closing Transactions

      A.     Background

      On February 14, 2001, in anticipation of the closing of the sale with respect

to Alrey Trust’s purchase of Davreyn’s stock, Alrey Trust entered into a stock

purchase agreement with Deutsche Bank for the sale of Davreyn’s Alcoa stock.

On the same day, Mr. Kramer accepted the Deutsche Bank offer on behalf of Alrey

Trust. The stock purchase agreement between Deutsche Bank and Alrey Trust

provided that the sale price would be determined on the basis of Alcoa’s closing

price on February 14, 2001. Alcoa stock closed at $35.49 per share on February

14, 2001.

      B.     Davreyn’s Liquidation and Other Post-Closing Transactions

      By documents dated February 15, 2001, Mr. Kramer, acting on behalf of

Alrey Trust, and Mr. Austin, acting as director of Davreyn, resolved that Davreyn
                                       - 20 -

be completely liquidated in accordance with section 331. In an attached plan of

liquidation Mr. Austin provided that Davreyn would distribute all of its assets to

Alrey Trust in redemption and cancellation of all of the outstanding Davreyn

stock. Further, on February 15, 2001, Mr. Austin authorized dissolution of

Davreyn and caused to be filed with the Virginia State Corporation Commission

articles terminating Davreyn’s corporate existence.

      Davreyn was liquidated on February 15, 2001, and its assets were

distributed to Alrey Trust. Mr. Austin directed Deutsche Bank to transfer the

Alcoa stock in Davreyn’s Deutsche Bank account to Alrey Trust’s account at

Deutsche Bank, and Deutsche Bank did so. In addition, Sunny Capital assigned to

Alrey Acquisition its shares of common stock of BMY Acquisition Corp.

(BMY).19 Davreyn was terminated and dissolved effective February 27, 2001.

      Pursuant to their earlier agreement, Alrey Trust ultimately transferred the

Alcoa stock to Deutsche Bank in exchange for $14,446,020 in net proceeds.20 On

February 20, 2001, Deutsche Bank deposited $14,446,010 of the net sales

      19
        Mr. Austin signed the assignment of shares document in his capacity as
trustee of Sunny Capital and as chairman of Alrey Acquisition.
      20
        The gross proceeds from the sale were $14,544,867. Deutsche Bank
calculated the net proceeds by eliminating from the gross proceeds the following
amounts: (1) commissions of $98,359, (2) a Securities and Exchange Commission
fee of $485, and (3) a handling fee of $3.
                                         - 21 -

proceeds into Alrey Trust’s account.21 Also on that day, Alrey Trust, at the

direction of Mr. Austin, transferred $16,139,452 from its account at First Union to

an account at ABN Amro Bank N.V., held under the name MeesPierson

(Bahamas) Ltd. Alrey Trust designated this amount as a “loan repayment”. After

the transfer Alrey Trust’s First Union bank account had a balance of $679,504.

      Between April 2001 and June 2003 a number of payments were made from

Alrey Trust’s First Union bank account to various entities and individuals,

including BDO Seidman, WC Investments, Inc.,22 Emil Pesiri,23 Bingham Dana

LLP, Sonnenschein, Cooper, Brown & Behrle, First Union, Vandalia, LLC, ICA,

and Starwalker Group, LLC (Starwalker).24 On June 19, 2003, Alrey Trust’s First

Union bank account was closed.

      21
         The $14,446,010 figure is equal to the net proceeds from Alrey Trust’s
sale of the Alcoa stock, minus a wire transfer fee of $10.
      22
       WC Investments, Inc., was owned by George Theofel. Mr. Theofel was a
former employee and/or representative of ICA.
      23
           Mr. Pesiri was a former employee and/or representative of ICA.
      24
        Starwalker was an entity established and owned by Mr. Austin. Mr.
Austin served as president of Starwalker during the relevant period.
                                      - 22 -

V.    Tax Reporting

      A.    Petitioner Trusts

      Each petitioner trust timely filed a Form 1041, U.S. Income Tax Return for

Estates and Trusts, for 2001. Mr. Griffin prepared petitioner trusts’ Forms 1041.

On a Schedule D, Capital Gains and Losses, attached to its Form 1041 the

Reynolds Trust reported a $2,664,196 gain from the stock sale. On Schedules D

attached to their Forms 1041, the Swords Trust, the Mackell Trust, and the

Brotherton Trust each reported a $3,628,247 gain from the sale of the Davreyn

common stock and from the redemption of Davreyn stock relating to the Goldman

Sacks fund shares. For 2001 petitioner trusts paid Federal income tax as follows:

Reynolds Trust--$532,722, Swords Trust--$726,356, Mackell Trust--$726,555,

and Brotherton Trust--$726,544.

      B.    Davreyn

      On September 30, 2002, Davreyn mailed to respondent a Form 1120, U.S.

Corporation Income Tax Return, for the period January 1 to February 15, 2001.25

Mr. Teig prepared the Form 1120 and Mr. Austin executed it.

      25
        Before the transactions at issue Davreyn used a TYE December 31 for
financial and tax accounting purposes.
                                        - 23 -

      On the Form 1120 Davreyn reported total income of $558,440, including

dividends of $61,475, interest of $24, and capital gains of $496,941. On an

attached Schedule D Davreyn reported a short-term capital gain of $496,941

attributable to the sale of the “investment in Davreyn LLC”. Davreyn reported a

basis in the Davreyn LLC investment of $1,076,530 and a sale price of

$1,573,471, and a Federal income tax liability of $37,560, on its Form 1120.

      C.     Alrey Trust

      Alrey Trust filed a Form 1041 for the taxable year beginning February 7,

2001, and ended January 31, 2002. Alrey Trust attached to its Form 1041 a

grantor letter identifying Alrey Acquisition as its grantor. The grantor letter

reported a long-term capital gain of $13,424,010, arising from the sale of 409,830

shares of Alcoa stock. The grantor letter stated that: (1) Alrey Trust acquired the

Alcoa stock on December 14, 1961, (2) Alrey Trust had a basis in the Alcoa stock

of $1,022,000, (3) Alrey Trust sold the Alcoa stock on February 15, 2001, for a

gross sale price of $14,446,010, and (4) Alrey Trust’s income, deductions, and

credits would be reported on Alrey Acquisition’s Federal income tax return.

      D.     Alrey Acquisition

      Alrey Acquisition filed a Form 1120 for the taxable year beginning

February 6, 2001, and ended January 31, 2002. On its Form 1120 Alrey
                                       - 24 -

Acquisition reported interest income of $10,506 and a net loss of $615,543, for a

total taxable loss of $605,037 and total tax of zero. On an attached Schedule D

Alrey Acquisition reported long-term capital gain from its passthrough entities of

$13,424,010 and a short-term capital loss of $13,727,689, resulting from its sale of

the BMY stock.26

      26
       With respect to the BMY stock, Alrey Acquisition reported a basis of
$13,744,939 and a sale price of $17,250. Alrey Acquisition reported that it
acquired the BMY stock on February 15, 2001, and that it sold the BMY stock on
December 17, 2001.

      Respondent has alleged that Alrey Acquisition’s sale of the Alcoa stock and
the BMY stock were parts of a Son-of-BOSS transaction. A Son-of-BOSS
transaction can be summarized as follows:

      [A] variation of a slightly older alleged tax shelter known as BOSS,
      an acronym for “bond and options sales strategy.” There are a
      number of different types of Son-of-BOSS transactions, but what they
      all have in common is the transfer of assets encumbered by significant
      liabilities to a partnership, with the goal of increasing basis in that
      partnership. The liabilities are usually obligations to buy securities,
      and typically are not completely fixed at the time of transfer. This
      may let the partnership treat the liabilities as uncertain, which may let
      the partnership ignore them in computing basis. If so, the result is
      that the partners will have a basis in the partnership so great as to
      provide for large--but not out-of-pocket--losses on their individual
      tax returns.

Kligfeld Holdings v. Commissioner, 128 T.C. 192, 194 (2007).
                                       - 25 -

VI.   Audit of Alrey Acquisition and Davreyn

      In June 2005 the Internal Revenue Service (IRS) began an examination of

Alrey Acquisition. As a result of the examination respondent issued to Alrey

Acquisition a notice of deficiency disallowing its claimed losses from the BMY

stock sale. By letters dated August 8, 2006, respondent informed petitioner trusts

that respondent had examined their potential transferee liability with respect to

Alrey Acquisition and determined that a transferee examination would not

proceed.

      In June 2006 the IRS began an examination of Davreyn. After examining

Davreyn’s Form 1120 respondent determined that the purported sale of Davreyn’s

stock to Alrey Trust should be recharacterized as a sale of assets by Davreyn

followed by a distribution of Davreyn’s assets to its shareholders in liquidation.

On the basis of this determination respondent increased Davreyn’s long-term

capital gain by $13,444,080 and determined a deficiency in its Federal income tax

of $4,602,986.

VII. Notice of Deficiency, Assessment, and Collection

      Respondent mailed to Davreyn a notice of deficiency dated September 23,

2008, for its TYE February 15, 2001. In the notice of deficiency respondent

determined a deficiency in Davreyn’s Federal income tax of $4,602,986, an
                                          - 26 -

addition to tax under section 6651(a)(1) of $1,160,137, an accuracy-related

penalty under section 6662 of $920,597, and accrued interest of $3,807,128.

      Davreyn did not file a petition in this Court contesting respondent’s

determinations. Accordingly, respondent treated the notice of deficiency as

defaulted and, on January 14, 2009, assessed Davreyn’s tax deficiency of

$4,602,986, as well as additions to tax under section 6651(a)(1) and (2) of

$1,160,137 and $1,982, respectively, an accuracy-related penalty under section

6662 of $920,597, and related interest.

VIII. Notices of Liability

      On February 25, 2010, respondent sent notices of liability to petitioner

trusts. In the notices of liability respondent identified Davreyn as the transferor

with an unpaid Federal income tax liability of $4,602,986, plus additions to tax, an

accuracy-related penalty, fees, and interest, for a total liability of $10,753,478.

Respondent determined each petitioner trust’s individual transferee liability on the

basis of the total amount each petitioner trust received in the stock redemption and

stock sale.27

      27
        Respondent calculated each petitioner trust’s individual transferee liability
as follows: (1) for the Reynolds Trust, respondent determined transferee liability
of $2,710,241, consisting of $2,673,431 in cash received and $36,810 in fees paid
to professional advisers and (2) for each of the Swords Trust, the Mackell Trust,
                                                                       (continued...)
                                        - 27 -

      In attached statements respondent advised petitioner trusts that the IRS did

not recognize their purported stock sale transactions with Alrey Trust. The

statements further advised that the amounts petitioner trusts received for the

purported stock sales would be attributable to them “in liquidation or distribution

of assets of Davreyn Corporation on or around” February 15, 2001. The

statements further explained that the purported stock sale transactions were

“substantially similar to an Intermediary transaction tax shelter described in Notice

2001-16 and Notice 2008-111.”

                                     OPINION

I.    Overview

      These cases involve several transactions which respondent now seeks to

reconfigure in a way that makes the assets of petitioner trusts a source of

collection for tax liabilities originally imposed on Alrey Trust and Alrey

Acquisition. In simple terms, Alrey Trust purchased all of the Davreyn stock from

petitioner trusts so that it could acquire Davreyn’s then principal asset, Alcoa

stock. With the benefit of hindsight, it now appears that Alrey Trust and Alrey

      27
        (...continued)
and the Brotherton Trust, respondent determined transferee liability of $3,833,988,
consisting of $3,416,891 in cash received, $370,050 attributable to the transfer of
the membership interests in Davreyn LLC, and $47,047 in fees paid to
professional advisers.
                                        - 28 -

Acquisition were established to participate in a preplanned series of interrelated

transactions designed to illegitimately avoid tax on Alrey Trust’s sale of

Davreyn’s Alcoa stock, which it had acquired as a liquidating distribution. Alrey

Trust sold the Alcoa stock incident to receiving it and reported that the substantial

gain on the sale was offset by an artificial loss resulting from what appears to have

been a Son-of-Boss transaction by Alrey Acquisition, the grantor of Alrey Trust.

      After assessing substantial tax liabilities against Alrey Trust, Alrey

Acquisition, and Davreyn, respondent now contends that petitioner trusts’ sales of

their Davreyn stock were part of a plan by petitioner trusts to illegitimately avoid

corporate tax on the distribution of the Alcoa stock in liquidation of Davreyn.

Respondent contends that his collection of the tax from petitioner trusts is under

the authority of section 6901. The Commissioner has likewise relied upon that

section to attempt to collect tax from claimed transferees in other similar cases

which have recently come before this Court. See, e.g., Hawk v. Commissioner,

T.C. Memo. 2012-154; Salus Mundi Found. v. Commissioner, T.C. Memo. 2012-

61, vacated and remanded sub nom. Diebold Found., Inc. v. Commissioner, 736
F.3d 172 (2d Cir. 2013); Slone v. Commissioner, T.C. Memo. 2012-57; Sawyer

Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, rev’d and remanded,

712 F.3d 597 (1st Cir. 2013); Feldman v. Commissioner, T.C. Memo. 2011-297,
                                       - 29 -

appeal docketed, No. 12-3144 (7th Cir. Sept. 18, 2012); Starnes v. Commissioner,

T.C. Memo. 2011-63, aff’d, 680 F.3d 417 (4th Cir. 2012). This Court concluded

in all but one of those cases that the Commissioner’s reliance on section 6901 to

impose transferee liability upon the claimed transferees was wrong. See Salus

Mundi Found. v. Commissioner, T.C. Memo. 2012-61 (decisions entered against

the Commissioner); Slone v. Commissioner, T.C. Memo. 2012-57 (decisions

entered against the Commissioner); Sawyer Trust of May 1992 v. Commissioner,

T.C. Memo. 2011-298 (decision entered against the Commissioner); Feldman v.

Commissioner, T.C. Memo. 2011-297 (decisions entered for the Commissioner);

Starnes v. Commissioner, T.C. Memo. 2011-63 (decisions entered against the

Commissioner).28 The Court of Appeals for the Fourth Circuit affirmed our

judgment in Starnes v. Commissioner, 680 F.3d 417, but the Courts of Appeals for

the First and Second Circuits did not do likewise in the Salus Mundi Found. and

the Sawyer Trust of May 1992 cases. See Diebold Found., Inc. v. Commissioner,

736 F.3d 172; Sawyer Trust of May 1992 v. Commissioner, 712 F.3d 597. This

Court subsequently determined upon remand from the Court of Appeals for the

      28
        In Hawk v. Commissioner, T.C. Memo. 2012-154, the Court denied the
taxpayers’ motion for summary judgment, concluding that genuine issues of
material fact remained in dispute as to whether they were liable as transferees
under sec. 6901.
                                       - 30 -

First Circuit that the disputed transferee in the Sawyer Trust of May 1992 case was

liable under section 6901 as a transferee of a transferee but concluded that the

liability was less than the Commissioner had determined. See Sawyer Trust of

May 1992 v. Commissioner, T.C. Memo. 2014-59.29 We decide the issue at hand

with this overview in mind.

II.   Section 6901(a)

      Section 6901(a) provides that the Commissioner may proceed against a

transferee of property to assess and collect Federal income tax, penalties, and

interest owed by the transferor (sometimes collectively, transferor’s unpaid taxes).

See also sec. 301.6901-1(a), Proced. & Admin. Regs. A transferee under section

6901 includes, among other persons, a shareholder of a dissolved corporation. See

sec. 301.6901-1(b), Proced. & Admin. Regs. Section 6901 does not impose

liability on the transferee but merely gives the Commissioner a procedure to

collect the transferor’s existing liability. Commissioner v. Stern, 357 U.S. 39, 42

(1958).

      29
       This Court has yet to decide Salus Mundi Found. v. Commissioner, T.C.
Memo. 2012-61, vacated and remanded sub nom. Diebold Found., Inc. v.
Commissioner, 736 F.3d 172 (2d Cir. 2013), following its remand from the Court
of Appeals for the Second Circuit.
                                        - 31 -

      The Commissioner may collect the transferor’s unpaid tax from the

transferee if an independent basis exists under applicable State law or State equity

principles for holding the transferee liable for the transferor’s debts. Sec. 6901(a);

Commissioner v. Stern, 357 U.S. at 45; Hagaman v. Commissioner, 100 T.C. 180,

183 (1993); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op. at 15. State

law determines the elements of liability, and section 6901 provides the remedy or

procedure to be employed by the Commissioner as the means of enforcing that

liability. Ginsberg v. Commissioner, 305 F.2d 664, 667 (2d Cir. 1962), aff’g 35
T.C. 1148 (1961); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op. at 15.

The applicable State law is the law of the State where the transfer occurred. See

Commissioner v. Stern, 357 U.S. at 45; Starnes v. Commissioner, 680 F.3d at 426.

      In sum, section 6901 allows the Commissioner to collect a taxpayers’s

unpaid tax from another person if three conditions are met. First, the taxpayer

must be liable for the unpaid tax. Second, the other person must be a “transferee”

within the meaning of section 6901. Third, an independent basis must exist under

applicable State law or State equity principles for holding the other person liable

for the taxpayer’s unpaid tax. Accord Diebold Found., Inc. v. Commissioner, 736
F.3d at 183-184; Sawyer Trust of May 1992 v. Commissioner, 712 F.3d at 604-

605. Section 6901 does not apply if one or more of these three conditions is not
                                        - 32 -

met. Accord Commissioner v. Stern, 357 U.S. 39; Diebold Found., Inc. v.

Commissioner, 736 F.3d at 183-184; Sawyer Trust of May 1992 v. Commissioner,
712 F.3d at 604-605; Starnes v. Commissioner, 680 F.3d at 430.

III.   Burden of Proof

       Section 6902(a) provides that in this Court the Commissioner bears the

burden of proving that a person is liable as a transferee. See also Rule 142(a), (d).

Section 6902(a) further provides that the Commissioner does not bear the burden

of proving that the transferor was liable for the tax which the Commissioner seeks

to collect by way of section 6901. See also Rule 142(d); cf. Rule 142(a)(1)

(generally stating the well-settled rule of Welch v. Helvering, 290 U.S. 111, 115

(1933), that the Commissioner’s determinations are presumed to be correct, and

taxpayers challenging those determinations bear the burden of proving them

wrong).

       Petitioners argue that notwithstanding section 6902(a), respondent bears the

burden of proving that Davreyn is liable for the tax determined in the notice of

deficiency. This is because, petitioners argue, section 7491(a) applies to shift the

burden of proof on that issue to respondent. Pursuant to section 7491(a), the

burden of proof shifts to the Commissioner as to any factual issue relevant to a

taxpayer’s liability for tax where the taxpayer introduces credible evidence with
                                        - 33 -

respect to the issue, sec. 7491(a)(1), and the taxpayer satisfies certain other

conditions, including substantiation of any item and cooperation with the

Government’s requests for witnesses and information, sec. 7491(a)(2). See also

Higbee v. Commissioner, 116 T.C. 438, 440-441 (2001).

      We need not and do not decide whether section 7491(a) applies to shift the

burden of proof as petitioners desire. This is because, as discussed below, we hold

that section 6901 does not apply to these cases because the record fails to establish

that an independent basis exists under applicable State law or State equity

principles for holding petitioner trusts liable for Davreyn’s unpaid tax and that

holding would remain the same even if we decided that Davreyn is liable for the

tax as determined in the notice of deficiency.

IV.   Parties’ Arguments

      Each party sets forth various arguments in the posttrial briefs. These

arguments include competing views on whether Davreyn is liable for the tax

determined in the notice of deficiency and whether petitioner trusts are

“transferees” within the meaning of section 6901.

      As we previously stated, our holding that section 6901 is inapplicable to

these cases would remain the same even if we decided that Davreyn is liable for

the tax determined in the notice of deficiency. The same would be true if we also
                                        - 34 -

decided that petitioner trusts are “transferees” within the meaning of section 6901.

Given that those two issues have no effect on our disposition of these cases, we

need not and do not decide those issues in this Opinion. We hereinafter assume

(but do not decide) that Davreyn is liable for the tax as determined in the notice of

deficiency and that petitioner trusts are “transferees” within the meaning of section

6901, and we confine our discussion to the parties’ dispute on whether applicable

State law and/or State equity principles hold petitioner trusts liable for Davreyn’s

unpaid Federal income tax. See also Commissioner v. Stern, 357 U.S. at 41-42;

Sawyer Trust of May 1992 v. Commissioner, 712 F.3d at 604-605; Starnes v.

Commissioner, 680 F.3d at 427, 430.

      Respondent urges the Court to adopt the following two-step analysis to

determine whether petitioner trusts, as transferees from Davreyn, are liable for

Davreyn’s unpaid tax: (1) analyze whether the subject transactions are recast

under Federal law, here primarily the Federal substance over form doctrine, and

then (2) apply State law to the transactions as recast under Federal law. One or

more transactions are recast or otherwise disregarded under the Federal substance

over form doctrine where the transactions, taken as a whole, show that the

transactions are shams or have no “purpose, substance, or utility apart from their

anticipated tax consequences.” Goldstein v. Commissioner, 364 F.2d 734, 740 (2d
                                        - 35 -

Cir. 1966), aff’g 44 T.C. 284 (1965); see also Commissioner v. Court Holding Co.,

324 U.S. 331 (1945); Gregory v. Helvering, 293 U.S. 465, 469-470 (1935); Rice’s

Toyota World, Inc. v. Commissioner, 752 F.2d 89, 95 (4th Cir. 1985), aff’g on this

issue 81 T.C. 184 (1983). The effect of this doctrine is that the substance and not

the form of the transactions determines their tax consequences. Commissioner v.

Court Holding Co., 324 U.S. at 333-334; Gregory v. Helvering, 293 U.S. at 469-

470; Rice’s Toyota World, Inc. v. Commissioner, 752 F.2d at 95; Lazarus v.

Commissioner, 58 T.C. 854, 864 (1972), aff’d, 513 F.2d 824 (9th Cir. 1975).

Alternatively, respondent contends, petitioner trusts, as transferees from Davreyn

and without regard to the Federal law characterization of the transactions, are

liable for Davreyn’s debts under applicable State law or State equity principles.

Petitioner trusts argue that they are not liable for Davreyn’s tax liability because,

they contend, (1) the transactions may be recast only under applicable State law,

which does not provide for any such recast, and (2) respondent failed to show that

they are liable for Davreyn’s debts under applicable State law or State equity

principles.

V.    Respondent’s Proposed Two-Step Analysis

      Respondent asks the Court to adopt his referenced two-step analysis of

transferee liability. We decline to do so. The U.S. Courts of Appeals for the First,
                                        - 36 -

Second, and Fourth Circuits have rejected the Commissioner’s requests to apply

that analysis, see Diebold Found., Inc. v. Commissioner, 736 F.3d at 184-185;

Sawyer Trust of May 1992 v. Commissioner, 712 F.3d at 604-605; Starnes v.

Commissioner, 680 F.3d at 428-429, and we do likewise. In the earliest appellate

opinion in that trilogy of cases, the U.S. Court of Appeals for the Fourth Circuit,

applying Commissioner v. Stern, 357 U.S. 39, held that the question of whether a

transfer occurred for purposes of section 6901 was separate from the question of

whether the transfer was fraudulent for State law purposes and concluded that

“Stern forecloses the Commissioner’s efforts to recast transactions under federal

law before applying state law to a particular set of transactions.” Starnes v.

Commissioner, 680 F.3d at 428-429. The Courts of Appeals for the First and

Second Circuits subsequently followed suit espousing similar rationales. See

Diebold Found., Inc. v. Commissioner, 736 F.3d at 185-186 (rejecting the

Commissioner’s argument that State law liability is determined on the basis of a

transaction as recast under Federal law); Sawyer Trust of May 1992 v.

Commissioner, 712 F.3d at 604-605;30 accord Ewart v. Commissioner, 814 F.2d
30
         In Sawyer Trust of May 1992 v. Commissioner, 712 F.3d 597, 604 (1st
Cir. 2013), rev’g and remanding T.C. Memo. 2011-298, the Commissioner argued
that this Court erred by: (1) failing to apply the Federal substance over form
doctrine to determine whether the taxpayer was a transferee before analyzing the
                                                                       (continued...)
                                        - 37 -

321, 324 (6th Cir. 1987) (the court, relying in part on Commissioner v. Stern, 357
U.S. 39, noted that: (1) section 6901 is a purely procedural statute, and (2) the

      30
         (...continued)
taxpayer’s liability under State law and (2) failing to find that the taxpayer had
constructive knowledge of the buyer’s tax avoidance scheme. The U.S. Court of
Appeals for the First Circuit rejected both arguments. Id. at 604-606. The court
found, however, that this Court failed to analyze whether the taxpayer was liable
under a provision of the Uniform Fraudulent Transfer Act that provides that a
transfer is fraudulent “‘if the corporation didn’t receive “reasonably equivalent
value” in return for the transfer and as a result was left with insufficient assets to
have a reasonable chance of surviving’”, even if the taxpayer lacked fraudulent
intent. Id. at 606-607 (quoting Boyer v. Crown Stock Distrib., Inc., 587 F.3d 787,
792 (7th Cir. 2009)). That court remanded the case to this Court to address that
issue. Id. at 606-612. Here, respondent did not argue in his opening brief that all
or any part of the subject transactions was fraudulent for lack of the receipt of
“reasonably equivalent value”. Nor did respondent notify us (or otherwise argue)
that the court’s opinion in Sawyer Trust of May 1992 v. Commissioner, 712 F.3d
597, which was released after these cases were fully briefed, was pertinent or
significant supplemental authority for our consideration of these cases. The
Commissioner, by contrast, did argue in the Starnes case that a transfer was
fraudulent for lack of the receipt of reasonably equivalent value. See, e.g., Starnes
v. Commissioner, 680 F.3d 417, 430 (4th Cir. 2012), aff’g T.C. Memo. 2011-63.
In addition, respondent did notify us in these cases that the Court of Appeals for
the Second Circuit decided Diebold Found., Inc. v. Commissioner, 736 F.3d 172
(2d Cir. 2013), vacating and remanding Salus Mundi Found. v. Commissioner,
T.C. Memo. 2012-61, after these cases were briefed. See discussion infra note 33.
Given our additional discussion infra pp. 43-45 that the Sawyer Trust of May 1992
case involved the Uniform Fraudulent Transfer Act and that Virginia has not
adopted that act (or its predecessor), and that the thrust of respondent’s argument
in these cases is that the Federal substance over form doctrine applies with full
force in determining transferee liability, we conclude that respondent has
consciously decided to forgo (or has otherwise waived) any argument that all or
any part of the subject transactions was fraudulent for lack of the receipt of
“reasonably equivalent value”.
                                         - 38 -

question of a taxpayer’s substantive liability is decided on the basis of State law),

aff’g 85 T.C. 544 (1985).

      This Court has previously never explicitly adopted or rejected respondent’s

proposed two-step analysis to decide whether a transaction should be recast under

the Federal substance over form (or similar) doctrine when analyzing whether a

transferee is liable under section 6901. Our approach, however, has been to

require that State law allow such a transaction to be recast under a substance over

form (or similar) doctrine before doing so. See Salus Mundi Found. v.

Commissioner, slip. op at 25 (“The law of the State where the transfer occurred (in

these cases, New York) controls the characterization of the transaction.”); Sawyer

Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 29-30, 34

(stating that “[t]he law of the State where the transfer occurred (in this case,

Massachusetts) controls the characterization of the transaction” and “[w]hether the

transactions should be ‘collapsed’ is a difficult issue of State law on which there is

fairly limited precedent”); Starnes v. Commissioner, T.C. Memo. 2011-63, slip op.

at 21-23 (discussing cases addressing whether certain transactions should be

collapsed under the Uniform Fraudulent Conveyance Acts of the corresponding

States); see also Diebold Found., Inc. v. Commissioner, 736 F.3d at 184 (stating

that this Court accepted Diebold’s position that under the Commissioner’s
                                        - 39 -

proposed two-step analysis, Federal law may be used to recharacterize a

transaction to determine whether someone is a transferee, but State law determines

whether to recharacterize the transaction when analyzing the transferee’s liability).

      Our Memorandum Opinion in Feldman v. Commissioner, T.C. Memo.

2011-297, does not compel a contrary conclusion. Accord Slone v.

Commissioner, slip op. at 25 n.9 (describing the facts in Feldman as “unique”).

The Court in Feldman v. Commissioner, slip op. at 25-37, applied the Federal

substance over form doctrine to recast a series of transactions and then, without

further explanation, applied State law to find the taxpayer liable as a transferee

with respect to the recast transaction. Moreover, unlike here (as discussed below),

there the Court found that “it is absolutely clear that all individuals involved * * *

were aware that * * * [the buyer] and its representatives had no intention of ever

paying the tax liabilities” and that the taxpayer and the buyer’s financing was a

sham transaction. Id. at 14, 19.

VI.   Applicability of State Law

      A.     Overview

      Respondent argues alternatively that petitioner trusts are liable under

applicable State law and/or State equity principles. In this vein, the parties agree

that Virginia law is the applicable State law for this purpose. Respondent argues
                                          - 40 -

more specifically that the applicable Virginia law is: (1) Va. Code Ann. sec. 55-80

(2012), which imposes liability on the grounds of actual fraud, (2) Va. Code Ann.

sec. 55-81 (2012), which imposes liability on the grounds of constructive fraud,

and (3) Virginia’s trust fund doctrine.

      We address the referenced statutory provisions and doctrine in turn. Before

doing so, however, we pause briefly to address the scope of the transaction to

which Virginia law will be applied.

      B.     Scope of Transaction

      Respondent argues primarily that Federal law sets the scope of the

transaction to which State law is applied. We disagree for the reasons stated

above. Respondent argues alternatively that Virginia has a substance over form

doctrine that applies to recast the series of transactions as one transfer between

each of petitioner trusts and Davreyn. Respondent relies on Burruss Timber Co. v.

Frith, 324 S.E.2d 679 (Va. 1985), to support his alternative argument that Virginia

has a substance over form doctrine that applies to these cases.

      Where a decision involves the applicability of State law, as it does here, we,

as a Federal court, must apply State law in the manner that the highest court of the

State has indicated that it would apply the law. See Commissioner v. Estate of

Bosch, 387 U.S. 456, 465 (1967); Estate of Young v. Commissioner, 110 T.C.
                                       - 41 -

297, 300, 302 (1998). If the State’s highest court has not spoken on the subject,

then we must apply State law as we see it, giving “proper regard” to relevant

rulings of other courts of the State. Commissioner v. Estate of Bosch, 387 U.S. at

465; see also Estate of Young v. Commissioner, 110 T.C. 300, 302. We should

follow an opinion on the subject by an intermediate appellate court of the State,

unless we conclude that the State’s highest court would decide otherwise. See

Commissioner v. Estate of Bosch, 387 U.S. at 465; Estate of Young v.

Commissioner, 110 T.C. 302.

      In the setting at hand, respondent bears the burden of establishing that the

Supreme Court of Virginia, that State’s highest Court, would apply a substance

over form doctrine to recast the series of transactions as a transfer between each of

petitioner trusts and Davreyn. See Kasishke v. United States, 426 F.2d 429, 435

(10th Cir. 1970); Bonney v. Commissioner, 247 F.2d 237, 239 (2d Cir. 1957)

(citing Helvering v. Fitch, 309 U.S. 149, 156 (1940), and Helvering v. Leonard,

310 U.S. 80, 86 (1940)), aff’g Towers v. Commissioner, 24 T.C. 199 (1955);

Dalton v. Commissioner, 34 T.C. 879, 885 (1960); Farnsworth v. Commissioner,

29 T.C. 1131, 1139 (1958), aff’d, 270 F.2d 660 (3d Cir. 1959). Respondent relies

erroneously on Burruss Timber Co., 324 S.E.2d 679, to meet that burden. In

Burruss Timber Co., the court considered whether a real estate broker earned a
                                          - 42 -

commission when he helped sell all of the stock of a corporate landowner, rather

than the specific landowner assets which the broker was hired to sell. The court

analyzed four similar cases from other jurisdictions and found that in each case,

the broker accomplished a transaction that was “substantially the equivalent” of

selling the assets and, consequently, that disallowing the broker commissions in

those cases would have allowed “form to triumph over substance.” Id. at 681-682.

The court declined to apply a substance over form doctrine to the transaction in

Burruss Timber Co. and concluded that the broker was not entitled to a

commission because the stock sale was not “substantially the equivalent” of the

assets sale for which he was hired. Id.

      In Burruss Timber Co. and in the cases discussed therein, the courts

considered the substance of the transaction only with respect to the effect of the

substance on a third party. The courts did not consider whether, with respect to

the legal rights and responsibilities of the parties to the transactions (i.e., the buyer

and the seller), the transactions should be collapsed, recast, or disregarded. The

Supreme Court of Virginia’s opinion in Burruss Timber Co. offers no guidance on

whether that court would apply the substance over form doctrine described therein

to determine the effects of a series of transactions on the actual parties to the

transactions.
                                         - 43 -

      Respondent has identified no other Virginia case that applied a substance

over form or similar doctrine. Nor has respondent argued that the transaction

should be collapsed under Virginia bankruptcy law.31 While respondent

references a number of Federal tax cases where a court applied Federal law to

disregard a transaction, those cases are inapposite in that they apply Federal law

rather than Virginia State law. Respondent has left us unpersuaded that the

Supreme Court of Virginia would apply a substance over form analysis to the

present setting.32 This is especially so given our finding, as discussed herein, that

petitioner trusts (through their trustees) did not as of the time that their stock was

sold have (or have reason to have) any inkling that the buyer, or someone related

      31
         In Sawyer Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298,
slip op. at 34, for example, this Court consulted decisions of bankruptcy courts to
decide which transaction or combinations of transactions should be considered as
the relevant transfer for purposes of the Massachusetts Uniform Fraudulent
Transfer Act. The approach there is supported by the fact that the Uniform
Fraudulent Transfer Act is based on, and consciously designed to operate in
accordance with the fraudulent transfer provisions in, the Bankruptcy Code. See
Prefatory Note, Unif. Fraudulent Transfer Act (1984), 7A (Part II), U.L.A. 4-7
(2006). As discussed infra p. 45, Virginia has not adopted the Uniform Fraudulent
Transfer Act.
      32
        Notwithstanding respondent’s citation of a single case from the Supreme
Court of Virginia, we have independently searched for additional Virginia cases
that could support a conclusion that the Supreme Court of Virginia would apply a
substance over form (or similar) doctrine in the setting at hand. We have not
found any case that would lead us to predict that it would.
                                        - 44 -

thereto, was acting to illegitimately avoid the payment of Federal tax. Petitioner

trusts believed that they were simply entering into a sale of their Davreyn stock

with a willing buyer.

      We also are unpersuaded that the Supreme Court of Virginia would apply a

substance over form analysis to the present setting because, as respondent asserts,

petitioner trusts and/or their representatives had actual or constructive knowledge

of Alrey Trust’s plan to sell the Alcoa stock and to illegitimately avoid any

resulting tax liability. Simply put, the record at hand does not lead us to find that

assertion as a fact. Cf. Diebold Found., Inc. v. Commissioner, 736 F.3d at 187-

190 (court concluded that shareholders had knowledge of illegitimate plan). After

these cases were briefed, the Court of Appeals for the Second Circuit decided

Diebold Found., Inc. v. Commissioner, 736 F.3d 172. There, the court collapsed

the series of transactions and found that there was a conveyance under the

applicable State statute, the New York Uniform Fraudulent Conveyance Act,

because, the court concluded, the taxpayers constructively knew of the entire

scheme to illegitimately avoid tax. Id. at 187-190. Neither party has requested

additional briefing in these cases in the light of Diebold Found., Inc.,33 and we

      33
       Respondent filed a notice of supplemental authority referencing Diebold
Found., Inc. v. Commissioner, 736 F.3d 172, and petitioners responded to that
                                                                    (continued...)
                                       - 45 -

conclude that Diebold Found., Inc. is factually distinguishable from these cases for

three reasons. First, while New York law reflects an adoption of the Uniform

Fraudulent Conveyance Act, Virginia has not adopted that act (or its successor the

Uniform Fraudulent Transfer Act) for the relevant period. See Grupo Mexicano

de Desarrollo, S.A. v. Alliance Bond Fund, Inc., 527 U.S. 308, 324 n.7 (1999);

Zazzali v. Swenson (In re DBSI, Inc., 463 B.R. 709, 718-719 (Bankr. D. Del.

2012); In re Best Prods. Co.), 168 B.R. 35, 52 (Bankr. S.D.N.Y. 1994). See

generally Isaac A. McBeth & Landon C. Davis III, “Bulls, Bears, and Pigs:

Revisiting the Legal Minefield of Virginia Fraudulent Transfer Law”, 46 U. Rich.

L. Rev. 273, 274 n.8 (2011-2012); id. at 276, 293 (stating that “as a general matter,

the provisions of the UFTA provide greater protection to creditors than Virginia’s

fraudulent transfer statutes” and analyzing “the UFTA provisions in comparison to

their Virginia counterparts and the UFTA provisions that have no Virginia

counterparts, so as to identify differences between the two bodies of fraudulent

transfer law”). Second, we are unaware of (and respondent has not cited) a

      33
         (...continued)
notice. Respondent acknowledged in his notice that the relevant State laws in
Diebold Found., Inc. and in these cases are different (New York and Virginia,
respectively) and made no attempt to harmonize the relevant New York law with
Virginia law. Petitioners agree that the relevant laws are different and conclude
further that the laws are irreconcilable.
                                         - 46 -

Virginia case that applies a collapsing doctrine similar to the New York doctrine

applied in Diebold Found., Inc. Third, even if respondent relied upon such a

doctrine, we find, contrary to the setting in Diebold Found., Inc., that neither

petitioner trusts nor their representatives knew (either actually or constructively)

of a scheme to avoid the tax liability in issue.34

      As to the third point, respondent invites the Court to conclude that petitioner

trusts were knowing participants in planning the series of transactions that

respondent maintains included the sale by petitioner trusts of Davreyn stock and

that they therefore are liable for the unpaid tax resulting from the plan. We

decline that invitation. In fact, the testimony of Ms. Swords, Ms. Mackell, and

      34
         The third point also persuades us that the Supreme Court of Virginia
would not collapse the transactions at issue in accordance with a certain rationale
espoused in LaRosa v. LaRosa, 482 Fed. Appx. 750, 2012 WL 1499522 (4th Cir.
2012), and Starnes v. Commissioner, 680 F.3d 417. In LaRosa, 482 Fed. Appx. at
755 n.3, the court noted in its application of West Virginia law that a court may
collapse a series of transactions into a single integrated transaction. The court
cited Official Comm. of Unsecured Creditors of Sunbeam Corp. v. Morgan
Stanley & Co. (In re Sunbeam Corp.), 284 B.R. 355, 370 (Bankr. S.D.N.Y. 2002),
which stands for the proposition that a series of transactions may be collapsed if
the transactions were linked and the transferee had actual or constructive
knowledge of the entire scheme. LaRosa, 482 Fed. Appx. 750. In Starnes v.
Commissioner, 680 F.3d at 433, the court, in applying North Carolina law, stated
that in deciding whether to collapse transactions in transferee liability cases, the
question is whether the taxpayer had actual or constructive knowledge that the
sold corporation would become delinquent on its taxes. We also note that the
relevant law in LaRosa and Starnes was that of West Virginia and North Carolina,
respectively, while the relevant law here is that of Virginia.
                                         - 47 -

Ms. Brotherton convinces us to make contrary findings; i.e., that there was no plan

by petitioner trusts to illegitimately avoid tax, that petitioner trusts had neither

actual nor constructive knowledge of Alrey Trust’s plan to sell the Alcoa stock

and to illegitimately avoid any resulting tax liability, that petitioner trusts were not

aware of circumstances that should have led them to make further inquiry

regarding Alrey Trust’s postclosing plans, and that petitioner trusts had neither

actual nor constructive knowledge that Alrey Trust would cause Davreyn to

become delinquent on its taxes. The testimony of Ms. Swords, Ms. Mackell, and

Ms. Brotherton emphasized that they were unaware of the financial buyer’s

identity and the reasons a financial buyer would want to purchase Davreyn’s stock

and that they relied on the advice of their accountants and lawyers. Ms. Swords,

Ms. Mackell, and Ms. Brotherton each testified that they did not previously try to

sell or liquidate Davreyn. Ms. Mackell testified that petitioner trusts did not

consider selling Davreyn until Mr. Griffin and Mr. Rohman approached petitioner

trusts in 2000 regarding the potential sale of their Davreyn stock. Ms. Swords and

Ms. Mackell both testified that petitioner trusts sold their Davreyn stock to Alrey

Trust on the basis of their advisers’ recommendation. Ms. Swords, Ms. Mackell,

and Ms. Brotherton repeatedly emphasized their complete trust in their advisers,

particularly Mr. Griffin. Ms. Swords, Ms. Mackell, and Ms. Brotherton each
                                           - 48 -

testified that they did not know the identity of Davreyn’s buyer and that they were

not aware that the buyer planned to sell Davreyn’s Alcoa stock and/or dissolve

Davreyn. We find all of this testimony to be credible.

      In addition, as to the potential tax consequences of liquidating Davreyn

rather than selling its stock, Ms. Brotherton testified that it was not advantageous

for petitioner trusts to liquidate Davreyn because doing so would subject her, Mr.

Reynolds, and Ms. Swords and Ms. Mackell to two levels of taxation. Ms.

Mackell testified further that she and her sisters did not consider liquidating

Davreyn because they knew petitioner trusts would incur significant tax liabilities.

Again, we find this testimony to be credible.

      In Slone v. Commissioner, slip op. at 23-24, the Court concluded that the

taxpayer was aware of the target corporation’s tax liabilities with respect to the

asset sale and that the acquiring corporation planned to offset gains resulting from

the asset sale. The taxpayer was unaware, however, that the acquiring corporation

planned to offset gains through an illegitimate scheme. Id. Here, Ms. Swords,

Ms. Mackell, and Ms. Brotherton did not know that Alrey Trust planned to sell the

Alcoa stock and generate a significant tax liability, and they were unaware that

Alrey Trust, through Alrey Acquisition, planned to offset any tax liability with

respect to Davreyn and/or to its assets.
                                        - 49 -

      Respondent emphasizes the fact that Mr. Rohman referred to the buyer’s

“peculiar tax situation” in a memorandum to Ms. Swords, Ms. Mackell, and Ms.

Brotherton. Respondent asks us to infer from this single phrase that petitioner

trusts were aware of Alrey Acquisition’s plan to illegitimately avoid the payment

of tax on the Alcoa stock sale gain. We are not prepared to draw such an

inference. Mr. Rohman testified that he included this phrase as a reference to the

fact that the buyer had losses or anticipated generating losses. As this Court noted

in Sawyer Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at

37, 45, and in Slone v. Commissioner, slip op. at 24, legitimate transactions may

be available to offset built-in gain, if recognized, and a taxpayer may contemplate

the execution of such a transaction. Accordingly, we will not infer from Mr.

Rohman’s use of the phrase “peculiar tax situation” that petitioner trusts were

aware of the details of Alrey Trust’s tax situation or that petitioner trusts knew

about, and agreed to facilitate, an illegal tax avoidance scheme. Because

petitioner trusts did not know of, approve, or have reason to suspect the multistep

plan by Alrey Acquisition and related entities to liquidate Davreyn, to sell the

Alcoa stock, and to attempt to illegitimately avoid the tax on that sale by engaging

in what likely was a Son-of-Boss transaction involving BMY stock, we decline to

reconfigure the sale by petitioner trusts of their Davreyn stock as respondent
                                        - 50 -

contends we should. We find to the contrary that petitioner trusts had no plan to

enable Davreyn, Alrey Trust, or Alrey Acquisition to illegitimately avoid tax and

that they engaged in an arm’s-length sale of Davreyn’s stock. Accord Sawyer

Trust of May 1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 44-45.

      Respondent contends that even if we conclude (which we do) that petitioner

trusts and their trustees had no plan to enable Davreyn, Alrey Trust, and/or Alrey

Acquisition to illegitimately avoid tax, petitioner trusts, through their

representatives Mr. Griffin and Mr. Rohman, knew that Alrey Trust planned to

offset the gain from the Alcoa stock sale and that the offset was the reason Alrey

Trust was interested in purchasing Davreyn. The record does not support this

contention, and we decline to find it as a fact. Neither Ms. Swords, Ms. Mackell,

nor Ms. Brotherton has a background in business or in tax, and we find that given

their lack of business experience, it was not unreasonable for them to rely on the

advice of their representatives that the stock sale transaction constituted a

legitimate transaction. See, e.g., Starnes v. Commissioner, 680 F.3d at 436-437.

Moreover, we are not persuaded that any of the representatives knew (either

actually or constructively) of the plan to illegitimately avoid tax on the Alcoa

stock sale. Mr. Griffin credibly testified that he did not know the identity of the

buyer or why the buyer wanted to purchase Davreyn stock. He testified that he did
                                        - 51 -

not discuss the buyer’s identity or tax situation with Mr. Rohman. Mr. Griffin also

testified that at the time of the sale, he did not know that the buyer was planning to

liquidate Davreyn or that the buyer planned to sell Davreyn’s Alcoa stock to

Deutsche Bank.

      Mr. Rohman’s testimony about the state of his knowledge is not quite so

satisfying; he openly acknowledged that he did not know or inquire as to why ICA

wanted to acquire PHCs like Davreyn. To his credit, however, he also testified

that he understood that the buyer had losses or anticipated losses. He apparently

came to this understanding on the basis of a conversation that took place before

the closing with Mr. Glazman, Mr. Gottlieb, or Mr. Teig. While Mr. Rohman

assumed that the buyer would want to offset these losses with gain, he testified

that he was not given any information regarding the buyer’s losses and that he had

no reason to question the legitimacy of the buyer’s losses. In addition, while Mr.

Rohman had structured previous sales similar to the transactions at issue, the

record does not persuade us that he knew that any of the buyers in those

transactions would cause the PHC to liquidate its stock and attempt to

illegitimately avoid Federal income tax that would be imposed as to the stock.

While the lack of due diligence by Mr. Rohman with respect to the buyer’s

identity and reputation is problematic, he adequately explained to us that he
                                        - 52 -

trusted ICA because ICA was represented by a good national law firm and a

respected international accounting firm and First Union, Alrey Trust’s trustor, was

a reputable financial institution. He also persuaded us that petitioner trusts had no

plan to undertake any steps except to sell Davreyn’s stock to the buyer.

      This Court in other transferee liability cases has considered similar

arguments regarding the knowledge of the taxpayer seller’s representatives and

has rejected them where the evidence was insufficient to prove that the taxpayer

seller knew of the buyer’s plan to illegitimately avoid tax. In Slone v.

Commissioner, slip op. at 23-24, for example, the taxpayers’ attorney sent a

memorandum to another of the taxpayers’ attorneys, explaining that the buyer

planned to offset the gain from the sale of the purchased corporation’s assets by

contributing to the nominal buyer assets with a high basis and low value, then

selling those assets at a loss before the end of the taxable year. The Court

concluded that this memorandum was insufficient to show that the taxpayers knew

of the corporate buyer’s illegitimate scheme. Id. at 24.

      It is clear from Mr. Rohman’s testimony that he at least suspected that the

buyer would sell the Alcoa stock and offset the gain from that sale with other

losses. It is likely that Mr. Griffin, an educated tax professional, also considered

such a possibility. There is no credible evidence, however, that either petitioner
                                        - 53 -

trusts or their representatives knew about any plan on the part of the buyer to

illegitimately avoid the payment of tax on the sale of Davreyn’s Alcoa stock, and

the representatives’ knowledge that an unrelated buyer planned to offset any gain

from a sale of the Alcoa stock with incurred or anticipated losses is insufficient to

show the existence of a preconceived plan by petitioner trusts to illegitimately

avoid tax. This Court has acknowledged that there are legitimate tax planning

strategies involving built-in gains and losses and that it was not unreasonable, in

the absence of contradictory information, for the representatives to believe that the

buyer had a legitimate tax planning method. See id. at 24; Sawyer Trust of May

1992 v. Commissioner, T.C. Memo. 2011-298, slip op. at 37, 45. We find that

while Mr. Rohman and Mr. Griffin knew or had reason to believe that the buyer of

petitioner trusts’ stock had tax attributes that made the purchase of the stock

attractive, Mr. Rohman and Mr. Griffin did not know or have reason to know that

any such tax attributes were improper or that the buyer intended to liquidate

Davreyn and to illegitimately avoid any resulting tax liability.35 We also find that

      35
         We are not unmindful of Notice 2001-16, 2001-1 C.B. 730, which was
released on January 19, 2001, and was formerly published in the Internal Revenue
Manual on February 26, 2001. The stock sale transaction at issue occurred on
February 15, 2001, after the release date but before the publication date. While
Mr. Griffin and Mr. Rohman were aware of this notice, they credibly explained to
us that they did not believe that it pertained to the Davreyn transaction. We also
                                                                        (continued...)
                                        - 54 -

neither Mr. Rohman nor Mr. Griffin was aware of any circumstance that would

have caused him to inquire further into the circumstances of the transaction, which

Mr. Rohman considered to be a simple stock sale.36

      In sum, we reject respondent’s contention that the transactions at issue

should be recast by applying a Virginia substance over form doctrine and decline

to collapse the transactions into a single integrated transaction. Instead, we find

on the basis of the record at hand that the sale by petitioner trusts of the Davreyn

stock to Alrey Trust was in form and in substance a sale of stock and that the

      35
        (...continued)
note that this Court has declined to find taxpayers liable as transferees with respect
to similar transactions where the transaction occurred both before issuance of
Notice 2001-16, supra, see Salus Mundi Found. v. Commissioner, T.C. Memo.
2012-61, and after its issuance, see Starnes v. Commissioner, T.C. Memo. 2011-
63.
      36
         In Diebold Found., Inc. v. Commissioner, 736 F.3d at 188, the Court of
Appeals for the Second Circuit concluded that this Court erred in finding that the
taxpayers’ representatives were not required to make further inquiry into the
circumstances of the transaction. To that end, the Court noted that the taxpayers
were sophisticated and well-represented persons who recognized the significant
tax liability arising from the built-in gains and specifically sought out multiple
persons to help them minimize that liability. Id. The court also noted that the
taxpayers’ representatives “had a sophisticated understanding of the structure of
the entire transaction” and had actively participated in implementing the
transaction. Id. at 188-189. The case of Diebold Found., Inc. is factually
distinguishable from these cases as to this point. Or put differently, respondent
has simply not persuaded us that a reasonably diligent person in the setting at hand
would have inquired further into whether Davreyn was going to pay its Federal tax
for FYE February 15, 2001. Cf. Starnes v. Commissioner, 680 F.3d at 433-437.
                                        - 55 -

transaction should not be recast as a sale of assets followed by a distribution in

liquidation. We proceed to evaluate each relevant transaction separately to decide

whether petitioner trusts are liable as transferees under Virginia law.

      C.     Actual Fraud: Va. Code Ann. Sec. 55-80 (2012)

      We begin our evaluation with Va. Code Ann. sec. 55-80, which provides:

             Every gift, conveyance, assignment or transfer of, or charge
      upon, any estate, real or personal, every suit commenced or decree,
      judgment or execution suffered or obtained and every bond or other
      writing given with intent to delay, hinder or defraud creditors,
      purchasers or other persons of or from what they are or may be
      lawfully entitled to shall, as to such creditors, purchasers or other
      persons, their representatives or assigns, be void. This section shall
      not affect the title of a purchaser for valuable consideration, unless it
      appear that he had notice of the fraudulent intent of his immediate
      grantor or of the fraud rendering void the title of such grantor.

The person seeking to set aside a conveyance as a fraudulent conveyance under

this section must prove that (1) “the transfer was made with the intent to delay,

hinder or defraud creditors” and (2) “the transferee had notice of the transferor’s

intent to defraud.” Coleman v. Cmty. Trust Bank, N.A. (In re Coleman), 299 B.R.
780, 795 (W.D. Va. 2003), aff’d in part, rev’d in part and remanded on other

issues, 426 F.3d 719 (4th Cir. 2005). A transferee’s fraudulent intent must be

proved with clear and convincing evidence. See Armstrong v. United States, 7 F.

Supp. 2d 758, 764 (W.D. Va. 1998).
                                        - 56 -

      Because it is difficult to prove fraudulent intent by direct evidence, fraud

may be established by circumstantial evidence, which includes various “badges of

fraud”. See id. These badges include: “(1) the close relationship of the parties,

(2) the grantor’s insolvency, (3) pursuit of the grantor by creditors at the time of

the transfer, (4) inadequate consideration, * * * (5) retention of possession of the

property by the grantor”, id., and (6) “fraudulent incurrence of indebtedness after

the conveyance”, In re Porter, 37 B.R. 56, 63 (Bankr. E.D. Va. 1984).

      Respondent contends that Davreyn transferred to petitioner trusts its assets

and cash in liquidation and petitioner trusts are substantively liable for Davreyn’s

unpaid tax because the transfer was fraudulent under Virginia law. Petitioners

contend that respondent erroneously collapsed a series of transactions into a single

transfer. Petitioners further contend that because there was no fraudulent transfer

from Davreyn to petitioner trusts, petitioner trusts cannot be liable as transferees

of Davreyn under Virginia law. We agree with petitioners.

      With the exception of Davreyn’s ownership interest in Davreyn LLC, which

was transferred to petitioner trusts through a redemption transaction which was not

fraudulent, Davreyn did not transfer anything to petitioner trusts. The sales of

Davreyn stock occurred between petitioner trusts and Alrey Trust. Accordingly,
                                        - 57 -

the relevant inquiry must focus on the value of the consideration petitioner trusts

exchanged with Alrey Trust.

      Alrey Trust paid petitioner trusts a total of $13,102,055 in exchange for

their Davreyn stock. Alrey Trust did not use Davreyn’s cash or its assets to

purchase the stock from petitioner trusts; instead, it borrowed the funds from a

third-party lender, Integrated Holdings. Davreyn was solvent at the time of the

stock sale transactions between petitioner trusts and Alrey Trust. At that time

Davreyn’s only outstanding tax liability related to the redemption transaction and

Davreyn had sufficient assets to pay its tax liability. We decline to find that any

transfer meeting the requirements of Va. Code Ann. sec. 55-80 occurred between

petitioner trusts and Davreyn or Alrey Trust.

      D.     Constructive Fraud

      We turn to Va. Code Ann. sec. 55-81, which provides:

             Every gift, conveyance, assignment, transfer or charge which is
      not upon consideration deemed valuable in law, or which is upon
      consideration of marriage, by an insolvent transferor, or by a
      transferor who is thereby rendered insolvent, shall be void as to
      creditors whose debts shall have been contracted at the time it was
      made, but shall not, on that account merely, be void as to creditors
      whose debts shall have been contracted or as to purchasers who shall
      have purchased after it was made. Even though it is decreed to be
      void as to a prior creditor, because voluntary or upon consideration of
      marriage, it shall not, for that cause, be decreed to be void as to
      subsequent creditors or purchasers.
                                        - 58 -

The person seeking to set aside a transfer under this section must show that: (1) a

transfer occurred, (2) the transfer was not supported by valuable consideration,

and (3) “‘the transfer was done when the transferor was insolvent or the transfer

rendered the transferor insolvent.’” Smith v. Porter (In re Carr & Porter, LLC),

416 B.R. 239, 260 (Bankr. E.D. Va. 2009) (quoting Wu v. Tseng, Nos. 2:06cv346,

2:06cv580, at *6 (E.D. Va. Jan. 24, 2007)). “[T]here must be a showing of

indebtedness existing at the time of the transaction.” Id. (citing C.F. Trust v.

Peterson, No. 1:97-CV-2003, 1999 WL 33456231, at *10 (E.D. Va. Jan. 8, 1999));

see also In re Porter, 37 B.R. at 65.

      The only asset Davreyn conveyed directly to petitioner trusts was its

ownership interest in Davreyn LLC, which held the Goldman Sachs fund shares.

However, this conveyance occurred before the stock sale transaction and did not

render Davreyn insolvent.

      At the time petitioner trusts sold their Davreyn stock to Alrey Trust,

Davreyn was solvent, possessing assets in excess of $14 million, and owed a tax

liability of $37,500 (the tax liability that arose in connection with the redemption

transaction). Alrey Trust paid a total of $13,102,055 to petitioner trusts in

exchange for Davreyn’s stock. In calculating the amount owed to petitioner trusts,

the parties to the stock sale left sufficient cash in Davreyn to pay the $37,500 tax
                                        - 59 -

liability from the redemption transaction. We find no constructive fraud on this

record.37

      E.     Virginia’s Trust Fund Doctrine

      We now turn to respondent’s contention that petitioner trusts are liable

under Virginia’s trust fund doctrine. In Marshall v. Fredericksburg Lumber Co.,

173 S.E. 553, 557 (Va. 1934), the Supreme Court of Appeals of Virginia stated:

      But where there are existing creditors of a corporation the
      stockholders will not be permitted, as against those creditors, to
      withdraw the assets of the corporation without consideration, whether
      it be done through a purchase of stock by the corporation or
      otherwise. We repeat that a stockholder is not entitled to a share of
      the capital assets of a corporation until the debts have been paid. * * *

In Marshall, 173 S.E. at 557-558, the corporation received no consideration for its

assets. The court emphasized that the transaction at issue was negotiated by the

corporation’s president, who was obligated “to conserve the assets of the

corporation and have them forthcoming for the purpose, primarily, of paying

corporation debts.” Id. at 558. In Ashworth v. Hagan Estates, Inc., 181 S.E. 381,

385 (Va. 1935), the Supreme Court of Appeals of Virginia quoted with approval a

      37
        The series of transactions designed to illegitimately avoid tax occurred
immediately after petitioner trusts sold their Davreyn stock to Alrey Trust. Those
transactions were planned and orchestrated by Alrey Trust and Alrey Acquisition
(and not petitioner trusts), and petitioner trusts had neither actual nor constructive
knowledge of those transactions or their purpose.
                                        - 60 -

Supreme Court of Oregon case stating that the concepts of the trust fund doctrine

apply “where a corporation transfers all its assets to another corporation with a

view of going out of business, and nothing is left with which to pay its debts”.

      Mr. Griffin and Ms. Swords, Ms. Brotherton, and Ms. Mackell did not take

any actions constituting a winding up or dissolution of Davreyn while serving as

the officers and directors of Davreyn. See Starnes v. Commissioner, T.C. Memo.

2011-63, slip op. at 31-32 (applying North Carolina’s trust fund doctrine in a

transferee liability case). When petitioner trusts sold their Davreyn stock, neither

petitioner trusts nor their representatives knew that Alrey Trust planned to

dissolve Davreyn. When Alrey Trust dissolved Davreyn, Mr. Austin was serving

as Davreyn’s sole director, and no one associated with petitioner trusts had any

role in structuring the sale of the Alcoa stock or in deciding to dissolve Davreyn.

Petitioner trusts had no interest in Davreyn when Alrey Trust dissolved it because

they had already sold all of their Davreyn stock.

      Davreyn was not insolvent when petitioner trusts sold their Davreyn stock.

Neither petitioner trusts nor Davreyn’s directors attempted to avoid any existing

debt of Davreyn. We decline to find on this record that petitioner trusts or

Davreyn’s directors took any actions before or at the time of the Davreyn stock

sale that would support the application of Virginia’s trust fund doctrine.
                                        - 61 -

VII. Conclusion

      Respondent has failed to establish that an independent basis exists under

applicable State law or State equity principles for holding petitioner trusts liable

for Davreyn’s unpaid tax. Accordingly, we hold that section 6901 does not apply

to these cases. We have considered the parties’ remaining arguments, and to the

extent not discussed above, conclude those arguments are irrelevant, moot, or

without merit.

      To reflect the foregoing,

                                                       Decisions will be entered for

                                                 petitioners.