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to the extent of his winnings1 of $1,800, and (4) made deductible
cash charitable contributions of $600. Expenses of these types
are deductible, if at all, as itemized deductions. Secs. 62(a),
63(d), 165(a), 165(d), 164(a)(1) and (2), 170(a)(1).
A taxpayer must keep records sufficient to establish the
amounts of the items required to be shown on his Federal income
tax return. Sec. 6001; sec. 1.6001-1(a), (e), Income Tax Regs.
In the event that a taxpayer establishes that a deductible
expense has been paid but is unable to substantiate the precise
amount, we generally 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.
Cohan v. Commissioner, 39 F.2d 540, 543-544 (2d Cir. 1930). We
cannot estimate a deductible expense, however, unless the
taxpayer presents evidence sufficient to provide some basis upon
which an estimate may be made. Vanicek v. Commissioner, 85 T.C.
731, 743 (1985).
Deductions for charitable contribution are subject to
further substantiation requirements. Sec. 170(a)(1). Generally,
a deduction for charitable contributions must be substantiated
with written records. Sec. 1.170A-13, Income Tax Regs.
Deductions for contributions of $250 or more are disallowed in
1Under sec. 165(d), a taxpayer’s losses from gambling are
deductible only to the extent of the taxpayer’s gains from
gambling.
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Last modified: May 25, 2011