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general rule, if the trial record provides sufficient evidence
that the taxpayer has incurred a deductible expense, but the
taxpayer is unable to adequately substantiate the precise amount
of the deduction to which he or she is otherwise entitled, the
Court may estimate the amount of the deductible expense, bearing
heavily against the taxpayer whose inexactitude in substantiating
the amount of the expense is of his own making, and allow the
deduction to that extent. Cohan v. Commissioner, 39 F.2d 540 (2d
Cir. 1930). However, in order for the Court to estimate the
amount of an expense, the Court must have some basis upon which
an estimate may be made. Vanicek v. Commissioner, 85 T.C. 731,
742-743 (1985). Without such a basis, any allowance would amount
to unguided largesse. Williams v. United States, 245 F.2d 559,
560-561 (5th Cir. 1957).
In the case of travel expenses, entertainment expenses, and
expenses paid or incurred with respect to listed property, e.g.,
passenger automobiles, section 274 overrides the Cohan doctrine,
and expenses are deductible only if the taxpayer meets the
section’s stringent substantiation requirements. Secs. 274(d),
280F(d)(4); Sanford v. Commissioner, 50 T.C. 823, 827-828 (1968),
affd. 412 F.2d 201 (2d Cir. 1969); sec. 1.274-5T(a), Temporary
Income Tax Regs., 50 Fed. Reg. 46014 (Nov. 6, 1985).
Section 274(d) specifically provides:
SEC. 274(d). Substantiation Required.--No deduction or
credit shall be allowed–-
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