3
Discussion
I. Facts
For most of his adult life, Mr. Feshbach has worked as an investment professional, both as a money manager and a private investor.
4
But he
hasn’t gone at
it alone. Essentially since they married, Mrs. Feshbach has been
, in her words, an extension of Mr. Feshbach’s professional
ventures, albeit at their home.
5
Beginning in the 1980s, Mr. Feshbach began using an investment strategy known as
“
selling short against the box.
”
This strategy served one primary purpose: delaying the recognition of taxable income. And unlike selling short generally
—
which involves an investor
’s
selling stock that he (or a broker on his behalf) borrows from another with the hope that the stock price will fall before the investor is required to buy identical stock to return to the person whose stock the investor sold
—
selling short against the box is in one way a far safer bet. An investor who sells short against the box borrows matching shares of an appreciated stock that the investor presently owns. The investor then sells the borrowed shares and posts the owned shares as collateral, thereby creating a long and short position in the same security. (Days long ago, the investor would place the owned, collateralized shares in a safe-deposit box
—
hence
the phrase “against the box.”
6
) This maneuver creates a neutral position, whereby any change in one position is always offset by an opposite, but balanced, change in the other position.
“You can’t lose; you can’t win,” Mr. Feshbach explained.
7
And here’s the upside:
selling short against the box locks in the built-in gain on the owned shares. Of course, an investor could similarly
4
Adv. Doc. No. 154 at 60:7-9.
5
Adv. Doc. No. 155 at 128:18-22.
6
S.K.
S
INGH
,
B
ANK
R
EGULATIONS
121 (2009).
7
Adv. Doc. No. 154 at 85:4.
Case 8:11-ap-00803-CPM Doc 170 Filed 10/17/17 Page 3 of 40