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transactions. Sec. 165(d); sec 1.165-10, Income Tax Regs.
Respondent determined that petitioner failed to substantiate
deductions that he claimed for gambling losses on his 1989 and
1992 income tax returns.
Petitioner bears the burden of proving error in respondent's
determination. Rule 142(a); INDOPCO, Inc. v. Commissioner, 503
U.S. 79, 84 (1992); Welch v. Helvering, 290 U.S. 111, 115 (1933).
Specifically, petitioner bears the burden of establishing that he
sustained the gambling losses that he claimed on his 1989 and
1992 income tax returns. Rule 142(a); Schooler v. Commissioner,
68 T.C. 867, 869 (1977). The issue is factual and must be
decided on the evidence presented. Green v. Commissioner, 66
T.C. 538, 544 (1976).
Section 6001 requires taxpayers to keep books and records
adequate to substantiate their income and deductions. See sec.
1.6001-1(a), Income Tax Regs.
If the trial record provides sufficient evidence that a
taxpayer has incurred a deductible expense, but the taxpayer is
unable to adequately substantiate the amount of the deduction to
which he or she is otherwise entitled, the Court may, under
certain circumstances, estimate the amount of such expense and
allow the deduction to that extent. Cohan v. Commissioner, 39
F.2d 540, 543-544 (2d Cir. 1930). However, in order for the
Court to estimate the amount of an expense, we must have some
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