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sold his A&W drive-in restaurant.
Since 1981, when petitioner opened Richard’s restaurant in
Hartford, he has operated it through an S corporation known as
Kedd, Inc. (Kedd). At all relevant times, petitioner was presi-
dent and owned 50 percent, and his spouse Melanie Mason (Ms.
Mason) was the secretary and the treasurer and owned 50 percent,
of the stock of Kedd.
In 1987, petitioner opened a second Richard’s restaurant in
New Castle, Indiana (New Castle). Petitioner operated the
Richard’s restaurant in New Castle through another S corporation
known as TRM, Inc. (TRM). During the year at issue, petitioner
and Ms. Mason each owned 50 percent of the stock of TRM. Some-
time thereafter, TRM ceased doing business because the Richard’s
restaurant located in New Castle was not profitable, and TRM was
generating losses.
From 1993 through at least the year at issue, petitioner
owned 100 percent of the stock of another S corporation, Prints
Unlimited, Inc. (Prints Unlimited), which operated an art gal-
lery. Sometime thereafter, Prints Unlimited, which was generat-
ing losses, ceased doing business.
At least during 1995 and 1996, petitioner was heavily
involved in investing in the stock market, which took a lot of
his time. During those years, petitioner purchased varying
numbers of shares of stock in at least 48 companies, which he
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