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expenses were incurred, and if so, through substantiation, the
amounts paid and hence allowable as deductions.
When a taxpayer establishes that he/she has incurred
deductible expenses but is unable to establish the exact amounts,
we can estimate the deductible amounts, but only if the taxpayer
presents sufficient evidence to establish a rational basis for
making the estimates. See Cohan v. Commissioner, 39 F.2d 540,
543-544 (2d Cir. 1930); Vanicek v. Commissioner, 85 T.C. 731,
742-743 (1985). In estimating the amount allowable, we bear
heavily on the taxpayer whose inexactitude in substantiating the
amount of the expense is of his own making. See Cohan v.
Commissioner, supra at 544. However, without a rational basis
for making the estimate, any allowance we make would amount to
unguided largesse. Williams v. United States, 245 F.2d 559, 560-
561 (5th Cir. 1957).
In the case of expenses paid or incurred with respect to
certain listed property, section 274 overrides the Cohan
doctrine, and those expenses are deductible only if the taxpayer
meets the stringent substantiation requirements of section
274(d). Sanford v. Commissioner, 50 T.C. 823, 827-828 (1968),
affd. per curiam 412 F.2d 201 (2d Cir. 1969).
Section 274 contemplates that no deduction may be allowed
for specified expenses on the basis of any approximation or the
unsupported testimony of the taxpayer. Sec. 1.274-5T(a),
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