T.C. Memo. 2011-177

UNITED STATES TAX COURT

JONATHAN S. AND TRACY A. LANDOW, Petitioners v.

COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket Nos. 15506-09, 20206-09. Filed July 25, 2011.

David D. Aughtry and Hale E. Sheppard, for petitioners.

Jennifer K. Martwick, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

CHIECHI, Judge: Respondent determined the following deficiencies in, additions under section 6651(a)(1)1 to, and 

1All section references are to the Internal Revenue Code in

effect at all relevant times. All Rule references are to the Tax

Court Rules of Practice and Procedure.
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accuracy-related penalties under section 6662(a) on petitioners’

Federal income tax (tax):

Year Deficiency

Addition to 

Tax Under 

Sec. 6651(a)(1)

Accuracy-Related

Penalty

Under Sec. 6662(a)

2003 $4,318,104.00 -- $863,620.80

2004 749.00 -- --

2005 93,009.45 $3,962.45 18,601.89

2006 89,040.00 -- 17,808.00

2007 211,976.00 16,300.70 42,395.20

The issues remaining for decision are:2

(1) Did a certain transaction in 2003 between petitioner

Jonathan S. Landow and Derivium Capital, LLC, constitute a loan

or a sale of securities? We hold that that transaction was a

sale of securities by petitioner Jonathan S. Landow.

(2) In the light of our holding with respect to issue 1, are

petitioners required to recognize under section 1042(e) any gain

realized on the sale of securities by petitioner Jonathan S.

Landow described in that issue? We hold that they are.

(3) In the light of our holdings with respect to issues 1

and 2, are petitioners entitled to defer under section 1033 any

gain realized on the sale of securities by petitioner Jonathan S.

Landow described in issue 1? We hold that they are not.

2Our resolution of the issues presented for petitioners’

taxable year 2003 in the case at docket No. 15506-09 resolves the

issues presented for their taxable years 2005, 2006, and 2007 in

the case at docket No. 20206-09. Petitioners concede the deficiency for their taxable year 2004, which is not related to the

issues presented here. 
- 3 -

FINDINGS OF FACT

All of the facts in these cases, which the parties submitted

under Rule 122, have been stipulated by the parties and are so

found.3

Petitioners resided in New York at the time they filed the

petitions in these cases. 

In 1994, petitioner Jonathan S. Landow (Mr. Landow) organized New York Medical, Inc. (NY Medical), under the laws of

Delaware. Mr. Landow has developed NY Medical into a successful

provider of medical services. 

Around early 2000, Mr. Landow was considering diversifying

his personal assets and simultaneously rewarding employees of NY

Medical through the establishment of an employee stock ownership

plan (ESOP). In May 2000, Mr. Landow contacted Irwin Selinger of

Corporate Solutions Group, LLC (CSG), an affiliate of American

Express Corporate Services, to assist him in establishing an ESOP

for NY Medical. Around July 25, 2000, NY Medical and CSG executed an agreement (ESOP advisory agreement) pursuant to which

CSG was to provide certain services to NY Medical, including

establishing and implementing an ESOP, financing that ESOP’s

purchase of certain stock of NY Medical from Mr. Landow, and

3The parties reserved objections based on relevancy to

certain of the stipulated facts. We need not and shall not

address those respective objections. That is because we have not

relied on any of the facts to which the parties reserved those

objections in resolving the issues presented.
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aiding Mr. Landow to defer under section 1042 any gain that he

realized on his sale of that stock. On a date not established by

the record, NY Medical established the New York Medical, Inc.,

Employee Stock Ownership Trust (NY Medical ESOP) that was to be

effective on January 1, 2000. 

At a time not established by the record between July and

November 2000, NY Medical and Mr. Landow decided to engage in a

so-called seller-financed ESOP transaction with leveraged qualified replacement property (QRP), as defined in section 1042. 

After that decision and pursuant to the ESOP advisory agreement,

CSG solicited on behalf of NY Medical certain information from

various financial institutions regarding the terms on which those

financial institutions would lend NY Medical the funds necessary

to purchase certain stock of that company from Mr. Landow. At a

time not established by the record, NY Medical decided to obtain

financing for that purchase from Citibank, N.A. (Citibank). 

On November 30, 2000, NY Medical, Mr. Landow, and Citibank

executed a letter agreement (Citibank letter agreement), and NY

Medical executed a demand note (Citibank demand note) payable to

Citibank. Pursuant to that letter agreement, Citibank agreed to

lend NY Medical $15 million, which was the amount payable under

that demand note. The Citibank letter agreement provided in

pertinent part:

As a condition to our [Citibank] making funds

available to NY Med[ical], NY Med[ical] shall use the
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proceeds to immediately make a $15,000,000 loan to the

ESOT [the NY Medical ESOP] (the “ESOT Loan”). The ESOT

shall use the proceeds of the ESOT Loan to purchase the

stock of NY Med[ical] from Landow. Landow shall use

the proceeds of the sale of the stock to make a loan to

NY Med[ical] (the “Sub Loan”). NY Med[ical] shall use

the proceeds of the Sub Loan to repay our advance [of

$15 million] under the Note. The proceeds shall be

advanced to each party under the Blocked Account Agreements[4] referred to above. This letter shall serve as

an instruction letter from each party to us to advance

the funds from each of the Blocked Accounts to fund the

ESOT Loan, the Stock purchase and the Sub Loan. NY

Med[ical] hereby instructs us to debit the Blocked

Account maintained on behalf of NY Med[ical] and apply

the amounts therein to repay the advance under the

Note. 

4On Nov. 30, 2000, NY Medical, the NY Medical ESOP, and Mr.

Landow separately executed respective documents, each of which

was titled “BLOCKED ACCOUNT AGREEMENT” (blocked account agreement). Each of those blocked account agreements contained

materially identical provisions. The blocked account agreement

that Mr. Landow executed provided in pertinent part:

 2. The Customer [Mr. Landow] has opened the

Pledged Account and will cause to be deposited therein

and will maintain therein cash from time to time. The

Customer hereby pledges to the Bank, and grants to the

Bank a lien, mortgage and security interest in, all

cash or other assets deposited from time to time in the

Pledged Account. At any time amounts are due and

payable to the Bank with respect to the obligations of

the Customer to the Bank, including the obligations

under Customer’s guaranty of the $15,000,000 Demand

Note of the New York Medical, Inc. to the Bank dated as

of the date hereof (the “Obligations”), whether prior

to or during the occurrence of a default or Event of

Default and whether or not Bank has made any demand or

the Obligations have matured, the Bank may, at its

discretion, may [sic] appropriate and apply the funds

in the Pledged Account to the payment of the Obligations. The Bank shall have sole dominion and control

over the Pledged Account. * * *
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Pursuant to the Citibank letter agreement, on November 30,

2000, (1) Citibank lent NY Medical $15 million, (2) NY Medical

used the proceeds of that loan in order to lend the NY Medical

ESOP $15 million, (3) the NY Medical ESOP used those proceeds to

purchase from Mr. Landow 450,000 shares of NY Medical’s stock for

$15 million, (4) Mr. Landow used those proceeds to lend NY

Medical $15 million, and (5) NY Medical used the proceeds of that

loan to pay Citibank $15 million in full satisfaction of its

obligation under the Citibank demand note. After the abovedescribed transactions were effected, Mr. Landow (1) did not

retain any cash from his sale of certain stock of NY Medical to

the NY Medical ESOP and (2) held a note of NY Medical in the

amount of $15 million evidencing his loan to that company. 

After the sale of certain of Mr. Landow’s stock of NY

Medical to the NY Medical ESOP, Mr. Landow sought to purchase

certain QRP in order to defer under section 1042 recognition of

any gain that he had realized on the sale of that stock. Because, as discussed above, Mr. Landow did not retain any cash

from his sale of certain stock of NY Medical to the NY Medical

ESOP, he was unable to buy that QRP without borrowing the funds

to do so. Citibank offered to extend Mr. Landow a line of credit

not exceeding $12 million in order to facilitate Mr. Landow’s

purchase of certain QRP. 
- 7 -

On November 1, 2000, NY Medical, Mr. Landow, and Citibank

executed a document titled “REVOLVING CREDIT NOTE (Multiple

Advances)” (revolving credit note). Pursuant to that note,

Citibank made available to Mr. Landow a line of credit not

exceeding $12 million (Citibank line of credit), which was a

recourse loan and on which Mr. Landow was allowed to draw during

the period November 1, 2000, to October 31, 2001. Pursuant to

the revolving credit note, in the event of Mr. Landow’s default

under that note Citibank retained “all of the rights and remedies

provided to it (i) under the Loan Documents, (ii) under applicable laws, and (iii) as a secured party by the Uniform Commercial

Code in effect in New York State at that time.” The revolving

credit note also required Mr. Landow to maintain a minimum net

worth of not less than $30 million. 

The revolving credit note permitted Mr. Landow to choose at

the time he drew against the line of credit thereunder one of two

alternative methods of calculating interest: (1) An interest

rate that was one percentage point greater than the LIBOR rate as

defined in that note5 or (2) an interest rate that was one and

5The revolving credit note defined the term “LIBOR rate” as

the interest rate that Citibank’s London office offered to prime

banks in the London interbank market. 
- 8 -

one-half percentage points less than the base rate as defined in

that note.6

On November 1, 2000, Mr. Landow executed a document titled

“General Hypothecation Agreement” (hypothecation agreement). 

Pursuant to that agreement, Mr. Landow pledged as security for

the Citibank line of credit certain rights to the QRP that he

intended to purchase with the loan proceeds that he borrowed

against that line of credit. In this regard, the hypothecation

agreement provided in pertinent part:

I. That, as security for all indebtedness and

other liabilities of the undersigned [Mr. Landow] * * *

pursuant to the Revolving Credit Note dated the date

hereof * * * (the “Note”), together with all obligations of the undersigned hereunder or under any other

document or agreement executed and delivered by the

undersigned in connection with the Note and this Agreement (the “Obligations”), the Lender [Citibank] shall

have and is hereby given a lien upon and a security

interest in any and all property in which the undersigned at any time has rights and which at any time has

been delivered, transferred, pledged, mortgaged or

assigned to, or deposited in or credited to an account

with, the Lender, or any third party(ies) acting in its

behalf or designated by it, including, but not limited

to, Pledged Collateral (as herein defined)[7] contained

6The revolving credit note defined the term “base rate” as

the interest rate that Citibank periodically published as its

base rate. 

7The hypothecation agreement defined the term “Pledged

Collateral” to mean:

The undersigned [Mr. Landow] will maintain at all times

in the Pledged Account assets acceptable to the Lender

[Citibank], consisting of Eligible Floating Rate Notes,

Eligible CP [commercial paper] and other marketable

securities, cash and cash equivalents. Such Eligible

(continued...)
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in the Pledged Account (as herein defined),[8] or otherwise at any time is in the possession or under the

control or recorded on the books of or has been transferred to the Lender, or any third party(ies) acting in

its behalf or designated by it, whether expressly as

collateral or for safekeeping or for any other or

different purpose, * * * and in any and all property in

which the undersigned at any time has rights and in

which at any time a security interest has been transferred to the Lender. Stock dividends and the distributions on account of any stock or other securities

subject to the terms and provisions hereof, including

FRN Interest (as herein defined)[9] shall be deemed an

increment thereto and if not received directly by the

Lender shall be delivered immediately to it by the

undersigned in form for transfer.

* * * * * * *

III. That, in addition to its rights and interests as herein set forth, the Lender may, at its option

at any time(s) following the occurrence of an Event of

Default and with notice to the undersigned, appropriate

and apply to the payment or reduction, either in whole

or in part, of the amount owing on any one or more of

the Obligations, whether or not then due, any and all

moneys now or hereafter with the Lender, any affiliate

of the Lender or any third party acting in its behalf

7(...continued)

Floating Rate Notes, Eligible CP and other marketable

securities, cash and cash equivalents, and any additional securities, cash and cash equivalents pledged to

the Lender from time to time and deposited in the

Pledged Account, together with any income and distributions in connection with the securities and any proceeds thereof deposited in the Pledged Account, as to

which the Lender has a perfected first position security interest * * * 

8The hypothecation agreement defined the term “Pledged

Account” to mean “Account No. * * * in the name of the undersigned [Mr. Landow] maintained by Citibank, N.A.”

9The hypothecation agreement defined the term “FRN Interest”

to mean “All interest paid in respect of Eligible Floating Rate

Notes and Eligible CP [commercial paper]”.
- 10 -

or designated by it, on deposit or otherwise to the

credit of or belonging to the undersigned, it being

understood and agreed that the Lender shall not be

obligated to assert or enforce any rights, liens or

security interests hereunder or to take any action in

reference thereto, and that the Lender may in its

discretion at any time(s) relinquish its rights as to

particular property or in any instance without thereby

affecting or invalidating its rights hereunder as to

any other property hereinbefore referred to or in any

similar or other circumstance.

* * * * * * *

VII. That the Lender may, at its option and

without obligation to do so, transfer to or register in

the name of its nominee(s), including any “clearing

corporation” or “custodian bank” as defined in the

Uniform Commercial Code in effect in New York State and

any nominee(s) thereof, all or any part of the aforementioned property and it may do so before or after the

maturity of any of the Obligations and with or without

notice to the undersigned.

VIII. That the Lender may assign or otherwise

transfer all or any of the Obligations, and may deliver

all or any of the property to the transferee(s), who

shall thereupon become vested with all the powers and

rights in respect thereof given to the Lender herein or

otherwise and the Lender shall thereafter be forever

relieved and fully discharged from any liability or

responsibility with respect thereto, all without prejudice to the retention by the Lender of all rights and

powers not so transferred. Furthermore that the Lender

may, in connection with any such assignment, transfer

or delivery, disclose to the assignee or transferee or

proposed assignee or proposed transferee any information relating to the undersigned furnished to the

Lender by or on behalf of the undersigned, provided,

that, prior to any such disclosure, the assignee or

transferee or proposed assignee or proposed transferee

shall agree to preserve the confidentiality of any

confidential information related to the undersigned

received by it from the Lender. 

* * * * * * *
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XV. That the following additional terms and

conditions are as set forth below:

* * * * * * *

(g) Minimum Collateral Value. The undersigned

shall comply with the following minimum collateral

value requirements.

* * * * * * *

 (iii) If at any time the undersigned has not

satisfied the obligation to deposit additional Pledged

Collateral or repay the Obligations as required in the

event of an FRN Facility Margin Call, such occurrence

shall be deemed an Event of Default, and the Lender

shall have the immediate right, without notice or other

action * * * to exercise any or all of the remedies

available to the Lender under this Agreement or otherwise, including the right to immediately sell the

Pledged Collateral. 

On November 1, 2000, NY Medical executed a document titled

“GENERAL SECURITY AGREEMENT”. Pursuant to that agreement, NY

Medical granted to Citibank a security interest in all of NY

Medical’s assets as collateral for its obligations under the

revolving credit note. 

Between November 2, 2000, and November 29, 2001, Mr. Landow

purchased as QRP the following floating rate notes (FRNs)10 at a

total cost of $15 million:

10A floating rate note is a debt instrument with a variable

interest rate that is determined on the basis of a certain

benchmark (e.g., the yield for U.S. Treasury bills). The interest rate on an FRN is adjusted periodically to reflect any

changes in the relevant benchmark. 
- 12 -

Date of

Purchase

Principal

Amount Issuer

Date of

Maturity

11/2/2000 $3,094,000 Proctor & Gamble 8/15/2050

11/2/2000 3,000,000 E.I. Dupont 12/27/2039

6/20/2001 3,000,000 Merck & Co. 12/27/2040

9/17/2001 3,000,000 United Parcel Service 6/21/2051

11/13/2001 1,500,000 Minnesota Mining 12/21/2041

11/29/2001 1,156,000 Minnesota Mining 12/21/2041

11/29/2001 250,000 E.I. Dupont 10/9/2041

(We shall refer collectively to the FRNs that Mr. Landow purchased between November 2, 2000, and November 29, 2001, as the

FRN portfolio.)

During December 2001, Mr. Landow received proposals from

certain financial institutions, including Citibank and J.P.

Morgan Chase, in which those institutions proposed to make

available to Mr. Landow a line of credit not exceeding $13.5

million. 

On February 11, 2002, Mr. Landow and petitioner Tracy A.

Landow (Ms. Landow) executed the following documents that amended

the revolving credit note and the hypothecation agreement: (1) A

document titled “Amended and Restated REVOLVING CREDIT NOTE

(Multiple Advances)” (amended revolving credit note) and (2) a

document titled “Amended and Restated General Hypothecation

Agreement” (amended hypothecation agreement). 

The amended revolving credit note amended the revolving

credit note by (1) increasing to $13.5 million the line of credit

that Citibank was to make available to Mr. Landow (Citibank
- 13 -

increased line of credit), (2) substituting Ms. Landow for NY

Medical as a borrower under that note, and (3) reducing to $15

million the minimum net worth that petitioners were to maintain.

In all other material respects, the amended revolving credit note

was identical to the revolving credit note. 

The amended hypothecation agreement did not make any material amendments to the portions of the hypothecation agreement

quoted above. The only amendments that the amended hypothecation

agreement made to the terms of that hypothecation agreement were

to (1) increase to $13.5 million the line of credit that Citibank

was to make available to Mr. Landow, (2) add reference to Ms.

Landow as a borrower on the amended revolving credit note, and

(3) delete from the definition of the term “Pledged Collateral”

the references in the hypothecation agreement to “Eligible CP”. 

(We shall refer to the transactions by which Citibank extended

the Citibank line of credit and the Citibank increased line of

credit, Mr. Landow drew upon those lines of credit to purchase

the FRNs, and he pledged as collateral those FRNs as the Citibank

transaction.)

As of December 31, 2002, the end of petitioners’ taxable

year 2002, Mr. Landow met the requirements of section 1042 with

respect to his sale of certain stock of NY Medical to the NY

Medical ESOP. As a result, Mr. Landow was not required to

recognize any of the gain that he realized on that sale. 
- 14 -

In proposing a line of credit to Mr. Landow, Citibank

informed him that the use of FRNs as QRP would achieve a result

known as “zero-cost borrowing”,11 which was Mr. Landow’s objective. However, Citibank failed to provide such zero-cost borrowing during 2001 and 2002. As a result, Mr. Landow did not meet

his objective of zero-cost borrowing and therefore Mr. Landow

retained CSG on June 12, 2002, in order to assist him in negotiating with a different lender a new loan of $13.5 million that

would replace the Citibank increased line of credit. 

From June to August 2002, Mr. Landow negotiated with Morgan

Stanley Dean Witter & Co. (Morgan Stanley) regarding that company’s refinancing the Citibank increased line of credit. On

June 17, 2002, Morgan Stanley sent Mr. Landow a letter in which

it proposed providing him with a so-called margin loan of $13.5

million at an interest rate equal to the three-month London

interbank offered rate plus 35 basis points.12 In that letter,

Morgan Stanley also indicated that, as security for such a loan,

it would require Mr. Landow to deposit with Morgan Stanley not

only the FRN portfolio but also $5 million of additional assets. 

11Zero-cost borrowing was possible, according to Citibank,

because the interest that Mr. Landow earned on the FRNs would

entirely offset the periodic interest that Citibank charged on

any line of credit that it made available to him. 

12A basis point is equal to 0.01 percent.
- 15 -

On July 10, 2002, Morgan Stanley sent Mr. Landow a second

letter in which it changed to its so-called cost-of-funds index

rate the interest rate that it would set for any margin loan that

it agreed to make to him.13 In that letter, Morgan Stanley also

proposed charging Mr. Landow a management fee of 1.25 percent of

the $5 million of assets that that company required as additional

security for any $13.5 million margin loan that it made to him. 

Around August 2002, CSG informed Mr. Landow about Derivium

Capital, LLC (Derivium). Sometime later in 2002, Mr. Landow

conducted certain research into Derivium and its founder, Charles

Cathcart (Mr. Cathcart). As part of that research, Mr. Landow

read numerous articles and other materials about Derivium and

Mr. Cathcart as well as certain marketing materials that Derivium

had prepared. In addition, Mr. Landow engaged certain independent financial advisors and legal advisors to assist him in

evaluating Derivium and any transactions that it might propose to

him. 

On August 19, 2002, Derivium prepared a separate document

titled “ESOP QRP LOAN--INDICATIVE FRN LOAN TERM SHEET” (proposed 

13Morgan Stanley’s cost-of-funds index rate was calculated

by using certain short-term interest rate indices. 
- 16 -

loan term sheet)14 with respect to each of Mr. Landow’s FRNs.15

In each of those documents, Derivium proposed to lend Mr. Landow

on a nonrecourse basis 90 percent of the face value of the FRN to

which the document pertained at a net interest rate calculated by

reference to either the one-month London interbank offered rate

or the three-month London interbank offered rate and taking into

account interest paid on that FRN. Each of the proposed loan

term sheets proposed prohibiting (1) Derivium from calling before

maturity the loan to which each such sheet pertained unless Mr.

Landow was in default on that loan and (2) Mr. Landow from

prepaying before maturity the principal of that loan. The

respective proposed loan term sheets set forth the terms of the

proposed loans as ranging from 27 to 38 years and required annual

net interest payments on those loans (i.e., the respective

14Our use of terms like “loan”, “lend”, “collateral”, “borrow”, “maturity”, and “interest” when describing the proposed

transaction and the actual transaction between Mr. Landow and

Derivium is for convenience only. Our use of any such terms is

not intended to imply, and does not imply, that the transaction

at issue between Mr. Landow and Derivium constitutes a loan for

tax purposes.

15Although we have found that Mr. Landow purchased seven

FRNs, he purchased on different dates in November 2001 two FRNs

issued by Minnesota Mining, both with maturity dates of Dec. 21,

2041. In making its proposals to Mr. Landow, Derivium treated

and referred to those two FRNs as one FRN, and for convenience we

shall refer to those two FRNs as one FRN. As discussed below,

Derivium proposed to make only one loan to Mr. Landow with

respect to the two FRNs issued by Minnesota Mining and separate

loans with respect to the remaining five FRNs that Mr. Landow

purchased, or a total of six loans. 
- 17 -

amounts, if any, that Mr. Landow was to pay after taking into

account the respective interest payments under the FRNs) that

ranged from $1,207.50 to $15,098.72 depending on the respective

face values of the FRNs. 

On August 29, 2002, Derivium sent Mr. Landow certain information with respect to the loans that Derivium proposed to make

to him (proposed Derivium loans), including a document titled

“MASTER AGREEMENT TO PROVIDE FINANCING AND CUSTODIAL SERVICES”

and a separate schedule A with respect to each of his FRNs. Each

of those schedules contained information that was materially

identical to the information contained in the respective proposed

loan term sheets that Derivium had prepared with respect to those

FRNs. 

On September 20, 2002, Derivium sent Mr. Landow certain

sample documents, including sample documents titled (1) “MASTER

AGREEMENT TO PROVIDE FINANCING AND CUSTODIAL SERVICES”,

(2) “SCHEDULE A-1 PROPERTY DESCRIPTION AND LOAN TERMS”, and

(3) “SCHEDULE D DISCLOSURE ACKNOWLEDGEMENT AND BROKER/BANK

INDEMNIFICATION”. 

From September 23 to 26, 2002, Derivium sent Mr. Landow

revised versions of certain of the documents that it had sent to

him on August 29, 2002. Those revised versions of those documents did not materially differ from the documents that Derivium

had sent to Mr. Landow on August 29, 2002. 
- 18 -

At Mr. Landow’s request, around January 16, 2003, Derivium

sent him revised versions of respective schedules A, numbered A-1

through A-6, with respect to the six loans for which his FRNs

were to serve as collateral (revised proposed schedules A).16

Each of those schedules provided that Mr. Landow was permitted to

pay before maturity the principal of the loan to which each such

schedule pertained but only under limited conditions. 

On a date not disclosed by the record between January 16 and

March 7, 2003, Mr. Landow requested from Derivium additional

revisions to certain of the documents that Derivium had sent to

him with respect to the proposed Derivium loans.17 On March 7,

2003, Mr. Cathcart sent to Mr. Landow a letter responding to that

request. That letter stated in pertinent part:

To address the concern about what would happen in a

bankruptcy setting, we have the following suggested

language that we have added in another case: “DC and

16The respective revised proposed schedules A, numbered A-1

through A-6, pertained to the respective loans for which the

following FRNs were to serve as collateral:

Schedule No. FRN

A-1 E.I. Dupont maturing 10/9/2041

A-2 United Parcel Service maturing 6/21/2051

A-3 E.I. Dupont maturing 12/27/2039

A-4 Merck & Co. maturing 12/27/2040

A-5 Minnesota Mining maturing 12/21/2041

A-6 Proctor & Gamble maturing 8/15/2050

17The record does not contain any letter or other communication by which Mr. Landow requested certain revisions to certain

of the documents that Derivium had sent him.
- 19 -

the Lender acknowledge that the Collateral is the asset

of the Client and is not subject to the claims of any

creditors of DC or the Lender.” Please let us know if

that would accomplish the intended need.

For the pre-payment provision, the Lender can agree to

pre-payment at five-year windows, with one-year advance

notice and a penalty of 6.0%. Please let us know if

that accomplishes the need in that area. 

Around April 9, 2003, Mr. Landow executed the following

documents with respect to the proposed Derivium loans: (1) A

document titled “MASTER AGREEMENT TO PROVIDE FINANCING AND

CUSTODIAL SERVICES” (Derivium master agreement), (2) respective

schedules A, numbered A-1 through A-6, with respect to the six

loans for which his FRNs were to serve as collateral titled “FRN

PROPERTY DESCRIPTION AND LOAN TERMS” (Derivium schedules A),18

and (3) a document titled “SCHEDULE D FRN DISCLOSURE ACKNOWLEDGEMENT AND BROKER/BANK INDEMNIFICATION” (Derivium schedule D).19

(We shall refer collectively to the Derivium master agreement,

the Derivium schedules A, and the Derivium schedule D as the

Derivium transaction documents.) The Derivium master agreement

and the Derivium schedules A were also executed by Derivium and

Bancroft Ventures Ltd. (Bancroft), a company which was located in

18Each of the Derivium schedules A, numbered A-1 through A6, pertained to the same loan and FRN as the revised proposed

schedule A with the same number. See supra note 16. 

19At no time before Apr. 9, 2003, the date on which Mr.

Landow and Derivium entered into the transaction at issue, did

Derivium request or require that Mr. Landow complete a loan

application or that he provide any personal financial information. 
- 20 -

the Isle of Man and which was the entity that served as the

lender under the Derivium transaction. 

The Derivium master agreement provided in pertinent part:

This Agreement is made for the purpose of engaging DC

[Derivium] to provide or arrange financing(s) and to

provide custodial services to the Client [Mr. Landow],

with respect to certain properties and assets (“Properties”) to be pledged as security, the details of which

financing and Properties are to be set out in loan term

sheets and attached hereto as Schedule(s) A (“Schedule(s) A”).

* * * * * * *

3. FUNDING OF LOAN

The contemplated Loan(s) will be funded according

to the terms identified in one or more term

sheets, which will be labeled as Schedule A, individually numbered and signed by both parties, and,

on signing, considered a part of and merged into

this Master Agreement. The Client understands

that by transferring securities as collateral to

DC and under the terms of the Agreement, the Client gives DC and/or its assigns, the right, without requirement of notice to or consent of the

Client, to assign, transfer, pledge, repledge,

hypothecate, rehypothecate, lend, encumber, short

sell, and/or sell outright some or all of the

securities during the period covered by the loan. 

The Client understands that DC and/or its assigns

have the right to receive and retain the benefits

from any such transactions and that the Client is

not entitled to these benefits during the term of

a loan. The Client agrees to assist the relevant

entities in completing all requisite documents

that may be necessary to accomplish such transfers.

4. RETURN OF CLIENT COLLATERAL

DC agrees to return, at the end of the loan term,

the same collateral (or cash equivalent if the

Client’s collateral securities have reached their

maturity date or the collateral has been called by
- 21 -

the issuer), as set out and defined in Schedule(s)

A attached hereto, upon the Client satisfying in

full all outstanding loan balances, including all

outstanding net interest payments due, if any,

and/or all late payment penalties due, if any.

5. REGISTRATION AND SUBCUSTODIANS

DC may place the Client Assets i) with any domestic or foreign depository or clearing corporation

or system that provides handling, clearing or

safekeeping services; ii) with the issuer of a

security in non-certificate form; iii) with any

domestic or foreign bank or depository as

subcustodian; and DC will pay the fees and expenses of the foregoing entities. 

Each of the Derivium schedules A provided in pertinent part:

3. Anticipated

Loan Amount: 90% of the face value * * *

4. Interest Rate: Loan interest rate (LIR) will be

indexed to [1 or] 3 month [as the

case may be] $US LIBOR (“LIBOR”)

* * *

5. Interest Interest on the collateral will be

Payments: received by the Lender and applied

against interest due on the Loan,

with the result that net interest

due per dollar on the Loan will be

determined by the * * * Annual Net

Interest Rate Formula * * * The

* * * formula reduces to the Annual

Net Interest Payment/Loan Amount.

* * * 

6. Late Payment A late fee of 5% of the Quarterly

Penalty: Net Interest Payment due will be

assessed for any Net Interest Payment past due by 30 days or more

and will be payable within 60 days

of the Net Interest Payment due

date.
- 22 -

7. Default: Borrower will be considered in

default if any Quarterly Net Interest Payment or late payment penalty

is past due by 90 days or more.

* * * * * * *

10. Prepayment: Except as provided for in Paragraph

14, prepayment of the Loan can be

made on any date which is a fiveyear anniversary date of this Loan,

provided DC is noticed of this

election at least one year prior to

a five-year anniversary date and a

pre-payment fee of 6.0% of the Loan

amount has been paid to DC or the

Lender at the time of said election.

11. Margin

Requirement: None, beyond initial collateral.

12. Non-Callable: Loan cannot be called by Lender

before maturity as long as Borrower

is not considered in Default. If

Borrower is in Default, the Loan

may be called by Lender at Lender’s

discretion.

13. Non-Recourse: Non-recourse to Borrower, recourse

against the Collateral only.

14. Creditor DC and the Lender acknowledge that

Claims: the Collateral is the asset of the

Client and is not subject to the

claims of any creditors of DC or

the Lender. Should any creditor of

DC or the Lender contest the ownership of the Collateral in any court

or similar proceeding, DC shall

provide immediate notice to the

Client and Client shall have the

right to prepay the Loan (without

any fee) and recover the Collateral

provided that the benefit of any

transaction entered into by DC or

the Lender shall be held by the

Client for DC’s or the Lender’s
- 23 -

benefit and such benefit shall be

the only compensation due to DC or

the Lender. 

The respective Derivium schedules A also provided as follows:

Schedule No.

Loan Term

(in years)

Annual Net

Interest

Payment Due

A-1 28 $921.25 

A-2 28 9,480.00 

A-3 36 11,055.00 

A-4 37 9,480.00 

A-5 38 9,322.56 

A-6 27 11,556.09 

The Derivium schedule D provided in pertinent part:

The Client understands that by transferring securities

as collateral to DC and under the terms of the Agreement, the Client gives DC the right, without notice to

the Client, to transfer, pledge, repledge, hypothecate,

rehypothecate, lend, short sell, and/or sell outright

some or all of the securities during the period covered

by the loan. The Client understands that DC has the

right to receive and retain the benefits from any such

transactions and that the Client is not entitled to

these benefits during the term of a loan. On repayment

of a loan in full by the Client, including all outstanding net interest payments due, if any, and/or all

late payment payment [sic] penalties due, if any, DC

has the obligation to return to the Client the same

collateral (or cash equivalent if the Client’s collateral securities have reached their maturity date or the

collateral has been called by the issuer), as set out

and defined in Schedule(s) A attached hereto. 

None of the Derivium transaction documents required Mr.

Landow to make any payments against the principal of the loans

before maturity of those loans. 

On April 14, 2003, Derivium executed a document titled

“LETTER OF AGREEMENT” as a supplement to the Derivium transaction
- 24 -

documents (Derivium letter agreement). That agreement provided

that Bancroft was to make certain payments and credits to Mr.

Landow to compensate him for (1) the accrued interest on each of

his FRNs that remained unpaid on the date of the closing of each

of the loans that Bancroft made to him and (2) the interest that

Wachovia Securities (Wachovia) was to charge him on certain

margin debt associated with the FRN portfolio between the time

that he transferred from Citibank to Wachovia that portfolio and

that margin debt and the time that he transferred to Bancroft’s

account with Wachovia that portfolio and that margin debt. 

Pursuant to the Derivium letter agreement, on May 5, 2003,

Bancroft sent Mr. Landow a check in the amount of $4,846.41 as

compensation for the interest that Wachovia charged him. 

On April 14, 2003, Mr. Landow sent Wachovia a letter in

which he gave it instructions with respect to his FRN portfolio

and certain transactions that he anticipated undertaking. That

letter stated in pertinent part:

Landow will deposit into the Account [a certain account

that Mr. Landow maintained at Wachovia] on April 16,

2003 the floating rate notes (“FRNs”) described below

[the FRN portfolio] * * *

Simultaneously with the receipt of an aggregate of

$13.5 million * * * hereinafter defined as “Total Loan

Proceeds Due” from Bancroft Ventures Limited

(“Bancroft”), you are irrevocably authorized and unconditionally instructed to transfer and deliver (in

essence, a delivery vs. payment transaction) the abovedescribed FRNs [the FRN portfolio] from the Account to

Bancroft * * *
- 25 -

Pursuant to the Derivium loan documents, on April 15, 2003,

Mr. Landow instructed Citibank to transfer the FRN portfolio from

a certain account that he maintained at Citibank to a certain

account that he maintained at Wachovia. Around the same date,

Citibank complied with those instructions and transferred the FRN

portfolio to Wachovia. 

On April 21, 2003, Mr. Landow executed certain documents

authorizing Wachovia to transfer each of Mr. Landow’s FRNs from

his account at Wachovia to a certain account that Bancroft

maintained at Wachovia. On the same date, Bancroft sold each of

those FRNs.20 Bancroft realized net sales proceeds of

$14,257,180.88 from the sale of the FRN portfolio. At the time

Bancroft sold the FRN portfolio, Mr. Landow was not aware of that

sale and did not become aware that Bancroft had sold the FRN

portfolio until some time after 2003. 

On April 22, 2003, Derivium sent Mr. Landow a facsimile. In

that facsimile, Derivium informed Mr. Landow (1) that Bancroft

had completed certain “hedging transactions” with respect to the

FRN portfolio, (2) that the total of the six loans that Bancroft

was to make to him was $13.5 million, and (3) that those loans

were to close and the proceeds were to be transferred to Mr.

Landow on April 24, 2003. 

20Bancroft’s sale of each of the FRNs was to settle on Apr.

24, 2003. 
- 26 -

On April 24, 2003, Bancroft transferred to Mr. Landow $13.5

million. (We shall refer collectively to the transactions in

which Mr. Landow transferred the FRN portfolio to Bancroft and

Bancroft transferred to Mr. Landow $13.5 million in cash as the

Derivium transaction.) On the same date, Derivium sent Mr.

Landow a facsimile in which it informed him that each of the six

loans had closed and that the proceeds of those loans totaling

$13.5 million had been transferred to his account at Wachovia. 

On April 24, 2003, Derivium sent Mr. Landow a second facsimile. 

Derivium included with that facsimile two documents titled

“VALUATION CONFIRMATION” and “ACTIVITY CONFIRMATION” (activity

confirmation documents), respectively, with respect to each of

the FRNs that Bancroft had sold on April 21, 2003. The respective activity confirmation documents listed the principal amounts

of the six loans and the total value of the collateral (i.e., the

FRNs) transferred to Bancroft with respect to those loans. 

After the Derivium transaction was effected, Mr. Landow used

a portion of the proceeds that he received as part of that

transaction to repay the outstanding balance on the Citibank

increased line of credit of $13.5 million. 

From around July 2003 through around April 2005, Bancroft

sent Mr. Landow the following with respect to each of the six

loans that it made pursuant to the Derivium transaction documents: (1) Quarterly account statements reflecting the interest
- 27 -

accrued on the loan, any credits arising from interest accrued on

the FRN that served as collateral for the loan, and the net

amount of interest due from Mr. Landow for each of the calendar

quarters ended June 30 and September 30, 2003, March 31, June 30,

September 30, and December 31, 2004, and March 31, 2005 and

(2) yearend account statements reflecting interest payments that

Mr. Landow made during each of the calendar years 2003 and 2004. 

From around October 2003 through August 2005, Mr. Landow paid

Bancroft for each calendar quarter for which he received an

account statement, except the quarter ended June 30, 2003,21 net

interest of $12,953.72. 

At a time during 2004 not established by the record, petitioners filed Form 1040, U.S. Individual Income Tax Return (Form

1040), for their taxable year 2003 (2003 joint return). In that

return, petitioners claimed, inter alia, a deduction of $167,159

for investment interest paid, including investment interest paid

to Citibank and Bancroft of $120,083 and $35,587, respectively. 

Petitioners attached to the 2003 joint return Schedule D, Capital

Gains and Losses (Schedule D), for their taxable year 2003 (2003

Schedule D). In that schedule, petitioners reported for their

21For the calendar quarter ended June 30, 2003, the interest

that accrued on the FRN portfolio during that quarter was greater

than the interest that accrued during that quarter on the six

loans that Bancroft had made to Mr. Landow. As a result, on July

14, 2003, Bancroft paid Mr. Landow the difference between those

amounts. 
- 28 -

taxable year 2003 a net short-term capital loss of $1,147,323

consisting of total short-term capital gains of $201,773 and a

short-term capital loss carryover from their taxable year 2002 of

$1,349,096. In the 2003 Schedule D, petitioners also reported

for their taxable year 2003 a net long-term capital loss of

$130,290 consisting of a long-term capital loss of $2,187 and a

long-term capital loss carryover from their taxable year 2002 of

$128,103. Petitioners claimed in the 2003 joint return a capital

loss of $3,000 and carried forward the remainder of the loss

reported in the 2003 Schedule D (i.e., $1,274,613) to their

taxable years 2004, 2005, 2006, and 2007. Petitioners did not

report in the 2003 Schedule D or anywhere else in the 2003 joint

return any gain with respect to the Derivium transaction. 

At a time during 2005 not established by the record, petitioners filed Form 1040 for their taxable year 2004 (2004 joint

return). In that return, petitioners claimed, inter alia, a

deduction of $45,278 for investment interest paid during that

year.22 Petitioners attached to the 2004 joint return Schedule D

for their taxable year 2004 (2004 Schedule D). In that schedule,

petitioners reported for their taxable year 2004 a net short-term

capital loss of $1,120,292 consisting of total short-term capital

22Petitioners netted the interest that accrued on Mr.

Landow’s FRNs against the interest that accrued on the six loans

that Bancroft had made to him and included the difference in the

investment interest for which they claimed a deduction in the

2004 joint return. 
- 29 -

gains of $24,031 and a short-term capital loss carryover from

their taxable year 2003 of $1,144,323. In the 2004 Schedule D,

petitioners also reported for their taxable year 2004 a net longterm capital loss of $215,987 consisting of total long-term

capital losses of $85,697 and a long-term capital loss carryover

from their taxable year 2003 of $130,290. Petitioners claimed in

the 2004 joint return a capital loss of $3,000 and carried

forward the remainder of the loss reported in the 2004 Schedule D

(i.e., $1,333,279) to their taxable years 2005, 2006, and 2007. 

Petitioners did not report in the 2004 Schedule D or anywhere

else in the 2004 joint return any gain with respect to the

Derivium transaction. 

On August 18, 2005, Bancroft sent Mr. Landow a letter in

which it informed him that “Optech Limited (‘Optech’) has acquired your Floating Rate Loan(s) from Bancroft Ventures Limited

(‘Bancroft’) and Optech is now the lender of record for your

transaction(s).” That letter also informed Mr. Landow that

interest payments due on the six loans, including interest due

for the calendar quarter ended June 30, 2005, were to be paid to

Optech Ltd. (Optech). 

From around August 2005 to around April 2007, Optech sent

Mr. Landow the following with respect to each of the six loans

that Bancroft had made pursuant to the Derivium transaction

documents: (1) Quarterly account statements reflecting the
- 30 -

interest accrued on the loan, any credits arising from interest

accrued on the FRN that served as the collateral for the loan,

and the net amount of interest due from Mr. Landow for each of

the calendar quarters ended June 30, September 30, and December

31, 2005, March 31, June 30, September 30, and December 31, 2006,

and March 31, 2007, and (2) yearend account statements reflecting

interest payments that Mr. Landow made during each of the calendar years 2005 and 2006. From around August 2005 to around

September 2007, Optech sent to Mr. Landow with respect to each of

the six loans that Bancroft had made to him an invoice for

interest due on the loan for each of the calendar quarters ended

June 30, 2005, through September 30, 2007. 

Around July 18, 2005, Mr. Landow engaged John W. Moscow (Mr.

Moscow), an attorney with the law firm of Rosner, Moscow &

Napierala, LLP. Mr. Landow engaged Mr. Moscow to investigate the

status of Bancroft and of the FRN portfolio that Mr. Landow had

transferred to Bancroft pursuant to the Derivium transaction

documents. 

On September 19, 2005, Mr. Landow sent Optech a letter in

which he requested that Optech provide him with documentation

evidencing that Optech had acquired the FRN portfolio from

Bancroft and where Optech was holding that portfolio. Mr. Landow

did not receive any response from Optech. On each of September

21 and October 25, 2005, and April 13, 2006, Mr. Landow contacted
- 31 -

Optech and restated his request that Optech provide him with

documentation evidencing that Optech had acquired the FRN portfolio from Bancroft and where Optech was holding that portfolio. 

Mr. Landow did not receive any response from Optech. 

Mr. Moscow sent Mr. Cathcart, Derivium’s founder, separate

letters on November 29, 2005 (November 29, 2005 letter), and

December 1, 2005 (December 1, 2005 letter), that were addressed

to different places regarding the Derivium transaction and

certain concerns of Mr. Landow about that transaction.23 Those

letters stated in pertinent part:

You have been the subject of a recent article in

Forbes magazine, as has Derivium Capital LLC and

Bancroft Ventures Ltd (IOM). My client, Dr. Landow, is

concerned about the custody and control of his securities [the FRN portfolio] * * *. As you know he negotiated a contract different from that proposed to others,

and he has every expectation that you will return his

securities to him. The sentence in the Forbes article

that you sold the stock is therefore extremely disturbing.

We have not received any notice pursuant to paragraph 14 of the Schedule A-4 FRN Property Description

and Loan Terms.[24] Given your contractual obligation

to return the securities and the absence of such notice

it is our expectation that you are in a position to

return the securities when obligated to do so. 

23The record does not establish whether Mr. Cathcart sent

Mr. Landow or Mr. Moscow any response to the November 29, 2005

letter or the December 1, 2005 letter. 

24Par. 14 of the “Schedule A-4 FRN Property Description and

Loan Terms” required Derivium to notify Mr. Landow in the event

that a creditor of Derivium or Bancroft contested ownership of

the FRN that was the subject of that schedule. 
- 32 -

Because Mr. Landow was unable to confirm that Optech had

acquired the FRN portfolio from Bancroft, around March 2006 he

opened a bank account with Long Island Commercial Bank in the

name of “Jonathan S. Landow FBO Accrued Interest Charges for

Floating Rate Note Portfolio” (interest escrow account). In

March 2006, Mr. Landow deposited into the interest escrow account

$51,814.88, which equaled four quarterly interest payments of

$12,953.72 on the six loans that Bancroft had made pursuant to

the Derivium transaction documents. Thereafter, and until April

2009, Mr. Landow deposited into the interest escrow account all

quarterly interest payments due on the six loans that Bancroft

had made pursuant to the Derivium transaction documents.

At a time during 2006 not established by the record, petitioners filed Form 1040 for their taxable year 2005 (2005 joint

return). In that return, petitioners claimed, inter alia, a

deduction of $109,906 for investment interest paid during that

year, including $51,815 that Mr. Landow paid to “BANCROFT &

SUCCESSOR” during that year.25 Petitioners attached to the 2005

joint return Schedule D for their taxable year 2005 (2005 Schedule D). In that schedule, petitioners reported for their taxable

year 2005 a net short-term capital loss of $991,991 consisting of

25Petitioners netted the interest that accrued on Mr.

Landow’s FRNs against the interest that accrued on the six loans

that Bancroft had made to him and included the difference in the

investment interest for which they claimed a deduction in the

2005 joint return. 
- 33 -

total short-term capital gains of $125,301 and a short-term

capital loss carryover from their taxable year 2004 of

$1,117,292. In the 2005 Schedule D, petitioners also reported

for their taxable year 2005 a net long-term capital loss of

$99,628 consisting of total long-term capital gains of $116,359

and a long-term capital loss carryover from their taxable year

2004 of $215,987. Petitioners claimed in the 2005 joint return a

capital loss of $3,000 and carried forward the remainder of the

loss reported in the 2005 Schedule D (i.e., $1,088,619) to their

taxable years 2006 and 2007. Petitioners did not report in the

2005 Schedule D or anywhere else in the 2005 joint return any

gain with respect to the Derivium transaction. 

At a time during 2007 not established by the record, petitioners filed Form 1040 for their taxable year 2006 (2006 joint

return). In that return, petitioners claimed, inter alia, a

deduction of $55,040 for investment interest paid during that

year, including $38,860 that Mr. Landow paid with respect to “FRN

NOTES” during that year.26 Petitioners attached to the 2006

joint return Schedule D for their taxable year 2006 (2006 Schedule D). In that schedule, petitioners reported for their taxable

year 2006 a net short-term capital loss of $1,082,140 consisting

26Petitioners netted the interest that accrued on Mr.

Landow’s FRNs against the interest that accrued on the six loans

that Bancroft had made to him and included the difference in the

investment interest for which they claimed a deduction in the

2006 joint return. 
- 34 -

of total short-term capital losses of $93,149 and a short-term

capital loss carryover from their taxable year 2005 of $988,991. 

In the 2006 Schedule D, petitioners also reported for their

taxable year 2006 a net long-term capital gain of $378,116

consisting of total long-term capital gains of $477,744 and a

long-term capital loss carryover from their taxable year 2005 of

$99,628. Petitioners claimed in the 2006 joint return a capital

loss of $3,000 and carried forward the remainder of the loss

reported in the 2006 Schedule D (i.e., $701,024) to their taxable

year 2007. Petitioners did not report in the 2006 Schedule D or

anywhere else in the 2006 joint return any gain with respect to

the Derivium transaction. 

At a time during 2008 not established by the record, petitioners filed Form 1040 for their taxable year 2007 (2007 joint

return). In that return, petitioners claimed, inter alia, a

deduction of $144,122 for investment interest paid during that

year, including $51,815 that Mr. Landow paid with respect to “FRN

NOTES” during that year.27 Petitioners attached to the 2007

joint return Schedule D for their taxable year 2007 (2007 Schedule D). In that schedule, petitioners reported for their taxable

year 2007 a net short-term capital gain of $2,522,746 consisting

27Petitioners netted the interest that accrued on Mr.

Landow’s FRNs against the interest that accrued on the six loans

that Bancroft had made to him and included the difference in the

investment interest for which they claimed a deduction in the

2007 joint return. 
- 35 -

of total short-term capital gains of $3,226,770 and a short-term

capital loss carryover from their taxable year 2006 of $704,024. 

In the 2007 Schedule D, petitioners also reported for their

taxable year 2007 a net long-term capital gain of $312,942

consisting of only long-term capital gains. Petitioners reported

in the 2007 joint return a capital gain of $2,835,688 consisting

of the net short-term capital gain and the net long-term capital

gain that they reported in the 2007 Schedule D. Petitioners did

not report in the 2007 Schedule D or anywhere else in the 2007

joint return any gain with respect to the Derivium transaction. 

On March 31, 2009, respondent issued to petitioners a notice

of deficiency (2003-2004 notice) with respect to petitioners’

taxable years 2003 and 2004. In that notice, respondent determined, inter alia, that the Derivium transaction constituted a

sale by Mr. Landow of the FRN portfolio with respect to which

petitioners are required to recognize a capital gain of $13.5

million.28

28Because of respondent’s determination with respect to the

Derivium transaction, respondent further determined in the 2003-

2004 notice to use the short-term loss carryover and the longterm loss carryover that petitioners claimed in the 2003 Schedule

D to offset a portion of the gain that respondent determined

resulted from the Derivium transaction. As a result, the capital

loss carryforward of $1,274,613 that petitioners claimed in their

2003 joint return was reduced to zero and was not available to

carry forward to their taxable years 2004, 2005, 2006, and 2007. 

However, because, as discussed above, petitioners reported in the

2004 Schedule D long-term capital losses for their taxable year

2004 in excess of short-term capital gains for that year, peti-

(continued...)
- 36 -

On July 6, 2009, respondent issued to petitioners a notice

of deficiency with respect to petitioners’ taxable years 2005,

2006, and 2007 (2005-2007 notice). In that notice, respondent

determined, inter alia, to reduce the respective capital loss

carryovers that petitioners had reported in their 2005 joint

return, their 2006 joint return, and their 2007 joint return. 

That determination was based on respondent’s determination in the

2003-2004 notice that the Derivium transaction constituted a sale

in 2003 by Mr. Landow of the FRN portfolio and that petitioners

are required to recognize a capital gain of $13.5 million for

their taxable year 2003. As discussed supra note 28, the shortterm loss carryover and the long-term loss carryover that petitioners claimed in the 2003 Schedule D were used to offset a

portion of the gain that respondent determined resulted from the

Derivium transaction. As a result, the capital loss carryover 

that petitioners claimed in their 2003 joint return was not

available to carry forward to any of their taxable years after

2003. 

As of around May 2010, Mr. Landow had not paid any of the

$13.5 million principal of the six loans that Bancroft had made

to him pursuant to the Derivium transaction documents. 

28(...continued)

tioners are entitled for their taxable year 2004 to the $3,000

deduction for capital losses that they claimed in their 2004

joint return.
- 37 -

OPINION

Petitioners bear the burden of proving that respondent’s

determination in the 2003-2004 notice that the Derivium transaction constitutes a sale in 2003 by Mr. Landow of the FRN portfolio is erroneous.29 See Rule 142(a); Welch v. Helvering, 290

U.S. 111, 115 (1933). 

Shortly before the parties filed their respective opening

briefs, we decided Calloway v. Commissioner, 135 T.C. 26 (2010).

We held on the basis of the facts presented there that a transaction between the taxpayer and Derivium in which the taxpayer

transferred to Derivium purportedly as collateral certain securities and Derivium purportedly lent the taxpayer an amount equal

to 90 percent of the fair market value of those securities

constituted the taxpayer’s sale of those securities, and not a

loan to the taxpayer of that amount. In reaching that holding,

we found that the taxpayer (1) transferred to Derivium legal

title to certain securities that he owned, (2) gave Derivium the

right to sell those securities at any time and without notice to

the transferor and to retain any and all benefits from any such

sale, and (3) left the taxpayer with at best an option to repur29As discussed above, our resolution of the issues presented

by respondent’s determination in the 2003-2004 notice that the

Derivium transaction constitutes a sale in 2003 by Mr. Landow of

the FRN portfolio resolves the issues presented by respondent’s

determinations in the 2005-2007 notice. See supra notes 2 and

28.
- 38 -

chase the securities at the end of the term of the purported loan

in question. Id. at 34-36.

In resolving the issue presented in Calloway, we relied on

various facts relating to the Derivium transaction at issue in

that case, including the following: (1) The taxpayer transferred

to Derivium under the agreements that he executed the securities

that he owned and gave it an unrestricted right to sell those

securities and retain all benefits from any such sale;30 (2) the

purported loan was nonrecourse; (3) except for the securities

that the taxpayer transferred to Derivium purportedly as collateral for the purported loan there were no margin requirements;

(4) the taxpayer was entitled to credit against the interest that

accrued on the purported loan from Derivium any dividends paid on

the securities that he transferred to that company; and

30In Calloway v. Commissioner, 135 T.C. 26, 29 (2010), the

agreement between the taxpayer and Derivium provided in pertinent

part:

“[Petitioner] understands that by transferring securities as collateral to * * * [Derivium] and under the

terms of the * * * [master agreement], * * * [petitioner] gives * * * [Derivium] the right, without

notice to * * * [petitioner], to transfer, pledge,

repledge, hypothecate, rehypothecate, lend, short sell,

and/or sell outright some or all of the securities

during the period covered by the loan. * * * [Petitioner] understands that * * * [Derivium] has the right

to receive and retain the benefits from any such transactions and that * * * [petitioner] is not entitled to

these benefits during the term of a loan. * * * [Emphasis added.]” [Bracketed insertions, asterisks, and

emphasis in Calloway.]
- 39 -

(5) Derivium did not require the taxpayer to make any payment of

the principal of the purported loan before maturity. Calloway v.

Commissioner, supra at 29, 34-36.

The facts listed above on which we relied in Calloway are

present in the instant cases. In the Derivium transaction at

issue here: (1) Mr. Landow transferred to Bancroft under the

Derivium transaction documents the FRNs that he owned and gave it

an unrestricted right to sell those FRNs and to retain all

benefits from any such sale;31 (2) each of the six loans that

Bancroft made to Mr. Landow pursuant to the Derivium transaction

documents were nonrecourse loans; (3) except for the FRNs that

Mr. Landow transferred to Derivium as collateral for the loans

that Bancroft made to him there were to be no margin requirements; (4) under each of the Derivium schedules A Mr. Landow was

entitled to credit against the interest accrued on each loan the

31The Derivium master agreement that Mr. Landow executed

provided in pertinent part:

The Client [Mr. Landow] understands that by transferring securities as collateral to DC [Derivium] and

under the terms of the Agreement, the Client gives DC

and/or its assigns, the right, without requirement of

notice to or consent of the Client, to assign, transfer, pledge, repledge, hypothecate, rehypothecate,

lend, encumber, short sell, and/or sell outright some

or all of the securities during the period covered by

the loan. The Client understands that DC and/or its

assigns have the right to receive and retain the benefits from any such transactions and that the Client is

not entitled to these benefits during the term of a

loan. 
- 40 -

interest accrued on each FRN that he transferred to Derivium;32

and (5) Derivium and Bancroft did not require Mr. Landow to make

any payments of the principal of any of the six loans before

maturity. 

Petitioners do not dispute that the facts listed above

relating to the Derivium transaction at issue here are materially

indistinguishable from the facts listed above relating to the

Derivium transaction at issue in Calloway v. Commissioner, supra. 

Petitioners argue, however, that there are certain other facts in

the present cases that make the Derivium transaction at issue

here materially distinguishable from the Derivium transaction at

issue in Calloway. Therefore, petitioners maintain, Calloway

does not control the resolution of whether the Derivium transaction at issue here constitutes a sale by Mr. Landow of his FRN

portfolio.33

32We do not find it material that in the present cases Mr.

Landow was required by the Derivium transaction documents to pay

quarterly to Bancroft the net difference between the interest

accrued on each of the six loans that Bancroft made to him

pursuant to those documents and the interest accrued on each of

the FRNs that he transferred to Bancroft, whereas in Calloway v.

Commissioner, supra at 29, the taxpayer was required to pay

interest only at the end of the three-year loan term. 

33Petitioners also contend that the Derivium transaction is

materially indistinguishable from the Citibank transaction which

respondent acknowledges constituted a loan by Citibank to Mr.

Landow that was collateralized by the FRN portfolio. Because of

respondent’s acknowledgment that the Citibank transaction constituted a loan to Mr. Landow and because petitioners maintain that

the Citibank transaction and the Derivium transaction are materi-

(continued...)
- 41 -

Petitioners point out that in the Derivium transaction at

issue here, unlike in the Derivium transaction at issue in

Calloway, (1) Mr. Landow did not enter into the Derivium transaction for the purpose of minimizing his risk of loss with respect

to the FRN portfolio and monetizing the value of that portfolio

without paying tax on the proceeds; (2) at all times petitioners

treated the Derivium transaction as a loan; and (3) Mr. Landow

“never surrendered his FRNs to Derivium or its affiliates, and

has taken significant steps to locate and recover the FRNs” in

contrast to the taxpayer in Calloway who “voluntarily surrendered

his collateral at the expiration of the three-year loan term”.34

33(...continued)

ally the same, petitioners assert (1) that the Derivium transaction constitutes six loans by Bancroft to Mr. Landow that were

collateralized by the FRN portfolio or (2) that the Citibank

transaction constituted a sale in 2000 by Mr. Landow of the FRN

portfolio. On the record before us, we reject petitioners’

contentions. On that record, we find the Citibank transaction to

be materially distinguishable from the Derivium transaction. 

34With respect to the third alleged difference between these

cases and Calloway v. Commissioner, supra, it appears that

petitioners are contending that Mr. Landow did not abandon his

obligations under the Derivium transaction documents and therefore did not allow Bancroft to retain the FRNs that he transferred to it. However, the six loans that Bancroft made to Mr.

Landow had terms ranging from 27 to 38 years, and none of those

loans had reached maturity as of the time that the parties

submitted these cases under Rule 122. More importantly, because

those six loans were nonrecourse loans, Mr. Landow, like any

other nonrecourse borrower, had the right to “walk away” from his

obligations to repay those loans and to allow the lender to

retain the FRNs that he had transferred to it.
- 42 -

Petitioners are correct that none of the above-listed facts

were present in Calloway v. Commissioner, 135 T.C. 26 (2010). 

However, those facts were present in Shao v. Commissioner, T.C.

Memo. 2010-189, and/or Kurata v. Commissioner, T.C. Memo. 2011-

64,35 two cases in which we held that Calloway was controlling

and that the respective transactions at issue in those cases

constituted sales of securities by the respective taxpayers, and

not loans to those respective taxpayers.36

In Shao v. Commissioner, supra, there was no evidence that

the taxpayer entered into the transaction for the purpose of

monetizing her securities without paying tax on the proceeds. 

Id. In fact, the taxpayer in Shao entered into the Derivium

transaction at issue in that case in order to replace a certain

margin account that she had maintained with a certain financial

institution. Id. Moreover, the taxpayer in Shao treated her

transaction as a loan at all times and did not “voluntarily

surrender” at the end of the term of her purported loan the

securities that she had transferred to Derivium as purported

35We decided Shao v. Commissioner, T.C. Memo. 2010-189, and

Kurata v. Commissioner, T.C. Memo. 2011-64, on the same day or

after the day the parties filed their respective reply briefs.

36On brief, petitioners cite repeatedly the concurring

opinion of Judge Holmes in Calloway v. Commissioner, 135 T.C. at

53, as support for certain of their arguments. We note that

Judge Holmes was the author of our opinion in Shao v. Commissioner, supra, which held Calloway to be controlling.
- 43 -

collateral for that purported loan. Id. Although the taxpayer

in Shao, like any other nonrecourse borrower, had the right to

“walk away” from the purported loan at the conclusion of the

three-year term of that purported loan, she chose to pay a

significant renewal fee in order to extend the term of the

purported loan. Id. Despite the foregoing factual differences

from Calloway v. Commissioner, supra, we held in Shao that

Calloway was controlling and that the Derivium transaction at

issue in Shao constituted a sale of securities by the taxpayer,

and not a loan to the taxpayer by Derivium. Shao v. Commissioner, supra.

In Kurata v. Commissioner, supra, there also was no evidence

that the taxpayers entered into the Derivium transaction at issue

there for the purpose of monetizing their securities without

paying tax on the proceeds. Id. Moreover, the taxpayers in

Kurata treated the transaction as a loan during the term of that

purported loan and reported gain from the sale of the securities

when they chose to surrender those securities at the conclusion

of the three-year term of the purported loan. Id. Despite these

factual differences from Calloway, we held in Kurata that

Calloway was controlling and that the Derivium transaction at

issue in Kurata constituted a sale of securities by the taxpayers, and not a loan to the taxpayers by Derivium. Kurata v.

Commissioner, supra.
- 44 -

Petitioners also point to certain other facts that they

contend make the Derivium transaction at issue here materially

distinguishable from the Derivium transaction at issue in

Calloway, including the following: (1) Mr. Landow retained the

ability to prepay the loan principal under the Derivium transaction documents and (2) those documents provided that the FRN

portfolio continued to be an asset of Mr. Landow.37

With respect to the provision in the Derivium transaction

documents involved here that gave Mr. Landow the right to prepay

the loan principal, which the taxpayer in Calloway did not have,

that right of Mr. Landow was extremely limited. He had the right

to prepay the loan principal only once every five years and only

after having given Derivium and Bancroft one-year advance notice. 

The purported loan at issue in Calloway was for a term of three

years, Calloway v. Commissioner, supra, which was two years less

than the earliest point at which Mr. Landow was able to prepay

the principal of his loan. Moreover, another condition to Mr.

Landow’s ability to prepay the loan principal was the requirement

that he pay at the time he gave the required notice a fee of 6

percent of the loan principal, which equaled $810,000--a signifi37As noted supra note 35, we decided Shao v. Commissioner,

supra, and Kurata v. Commissioner, supra, on the same day or

after the day the parties filed their respective reply briefs. 

If those two cases had been released before the parties filed

their respective briefs, we presume that petitioners would have

pointed out that the facts listed below were not present in those

cases.
- 45 -

cant disincentive to Mr. Landow’s exercising his prepayment

right.

With respect to the provision in the Derivium transaction

documents that the FRN portfolio was to remain the asset of Mr.

Landow, we find that provision to be meaningless. This is

evidenced by the fact that on the same date on which Mr. Landow

transferred the FRNs to Bancroft, Bancroft sold those FRNs, which

it was expressly allowed to do in those documents, and used 90

percent of the sale proceeds to make the six loans in question to

Mr. Landow. 

Based upon our examination of the entire record before us,

we find that the Derivium transaction at issue here is not

materially distinguishable from the Derivium transaction at issue

in Calloway v. Commissioner, supra. On that record, we further

find that Calloway is controlling in these cases. On the record

before us, we find that the Derivium transaction constitutes a

sale by Mr. Landow of the FRN portfolio to Bancroft, and not a

loan by Bancroft to Mr. Landow that was collateralized by that

portfolio.

We turn now to petitioners’ argument that if we were to

find, as we have, that the Derivium transaction at issue here

constitutes a sale by Mr. Landow of the FRNs, they would not be

required under section 1042(e) to recognize any gain that Mr.

Landow realized as a result of that sale. That is because,
- 46 -

according to petitioners, gain under that section is recognized

only where the taxpayer disposes of qualified replacement property (i.e., the FRN portfolio), and Mr. Landow did not dispose of

the FRN portfolio; Derivium did. 

Petitioners’ argument misreads our Opinion in Calloway v.

Commissioner, 135 T.C. 26 (2010). In Calloway, an important fact

was that Derivium sold the taxpayer’s stock immediately after the

taxpayer transferred it to Derivium. Id. at 34-36, 38-39. That

fact, combined with other facts, led us to hold in Calloway that

the taxpayer sold his stock when he transferred it to Derivium. 

Id. at 39. We did not hold in Calloway, as petitioners suggest,

that Derivium’s immediate sale of the taxpayer’s stock constituted the sale with respect to which the taxpayer was subject to

tax. Id. In making their argument under section 1042(e),

petitioners are focusing on the wrong transaction, namely,

Bancroft’s immediate sale of the FRNs. The transaction on which

we must focus to address petitioners’ argument under section

1042(e) is Mr. Landow’s disposition by sale of the FRNs to

Bancroft.

On the record before us, we have found that Mr. Landow sold

the FRN portfolio when he transferred that portfolio to Bancroft

pursuant to the Derivium transaction documents. On that record,

we further find that petitioners are required under section
- 47 -

1042(e) to recognize for their taxable year 2003 any gain that

Mr. Landow realized as a result of that sale.

Petitioners also argue that if we were to find, as we have,

that the Derivium transaction constitutes a sale by Mr. Landow of

the FRNs, that sale would constitute a theft and therefore an

involuntary conversion under section 1033(a).38 Consequently,

38Sec. 1033(a) provides in pertinent part:

SEC. 1033. INVOLUNTARY CONVERSIONS.

(a) General Rule.--If property (as a result of its

destruction in whole or in part, theft, seizure, or

requisition or condemnation or threat or imminence

thereof) is compulsorily or involuntarily converted--

* * * * * * *

(2) Conversion into money.--Into money or

into property not similar or related in service or

use to the converted property, the gain (if any)

shall be recognized except to the extent hereinafter provided in this paragraph:

(A) Nonrecognition of gain.--If the

taxpayer during the period specified in subparagraph (B), for the purpose of replacing

the property so converted, purchases other

property similar or related in service or use

to the property so converted, or purchases

stock in the acquisition of control of a

corporation owning such other property, at

the election of the taxpayer the gain shall

be recognized only to the extent that the

amount realized upon such conversion (regardless of whether such amount is received in

one or more taxable years) exceeds the cost

of such other property or such stock. Such

election shall be made at such time and in

such manner as the Secretary may by regulations prescribe. * * *
- 48 -

according to petitioners, they are entitled to purchase replacement property as required by section 1033(a)(2)(A) and thereby

defer under section 1033(a) any gain that Mr. Landow realized as

a result of that sale. 

In Wheeler v. Commissioner, 58 T.C. 459 (1972), we explained

the scope and the purpose of section 1033 as follows:

Congress clearly intended to extend the benefits of

section 1033 * * * only to public takings and casualtylike conversions, and the limitation of its benefits to

involuntary conversions--i.e., those “wholly beyond the

control of the one whose property has been taken”--

reflects that intent.

Id. at 463 (quoting Dear Publ. & Radio, Inc. v. Commissioner, 274

F.2d 656, 660 (3d Cir. 1960), affg. 31 T.C. 1168 (1959)). 

Mr. Landow voluntarily entered into the Derivium transaction

in which he transferred to Bancroft the FRN portfolio in exchange

for $13.5 million in cash and gave Bancroft the right, inter

alia, to sell the FRN portfolio without notice to him and to

retain the proceeds of that sale. 

On the record before us, we find that Mr. Landow’s sale of

the FRN portfolio to Bancroft in exchange for $13.5 million in

cash does not constitute an involuntary conversion, as defined in

section 1033. On that record, we further find that petitioners

are not entitled to defer under that section any gain that Mr.

Landow realized as a result of that sale.39

39In the light of our finding that petitioners are not

(continued...)
- 49 -

We have considered all of the contentions and arguments of

the parties that are not discussed herein, and we find them to be

without merit, irrelevant, and/or moot.

To reflect the foregoing and the concessions of the parties,

Decisions will be entered

under Rule 155.

39(...continued)

entitled to defer under sec. 1033 any gain that Mr. Landow

realized as a result of his sale of the FRNs, we need not and

shall not address petitioners’ argument that they are entitled to

an extension of the period under sec. 1033(a)(2)(B) within which

they must purchase replacement property.