- 6 -
Heininger, 320 U.S. 467, 475 (1943). An expense is ordinary
under section 162 if it bears a reasonably proximate relationship
to the operation of the taxpayer's business. Deputy v. du Pont,
308 U.S. 488, 495-496 (1940); Gill v. Commissioner, T.C. Memo.
1994-92, affd. without published opinion 76 F.3d 378 (6th Cir.
1996). An expense is necessary if it is helpful and appropriate
in promoting and maintaining the taxpayer's business. Carbine v.
Commissioner, 83 T.C. 356, 363 (1984), affd. 777 F.2d 662 (11th
Cir. 1985).
Taxpayers must substantiate amounts claimed as deductions by
maintaining the records necessary to establish their entitlement
thereto. Sec. 6001; Hradesky v. Commissioner, 65 T.C. 87, 90
(1975), affd. per curiam 540 F.2d 821 (5th Cir. 1976).
Where a taxpayer establishes his entitlement to a deduction,
but does not establish the amount because of the lack of
documentary evidence, the Tax Court should estimate the amount
allowable, Cohan v. Commissioner, 39 F.2d 540, 543-544 (2d Cir.
1930), provided there is enough evidence in the record to provide
a rational basis for an estimate, Williams v. United States, 245
F.2d 559, 560 (5th Cir. 1957); Vanicek v. Commissioner, 85 T.C.
731, 743 (1985).
In Cohan v. Commissioner, supra at 543, the Court of Appeals
for the Second Circuit recognized that the expenses of an
impresario in entertaining actors and crew members were
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