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disclosures must adequately apprise the Commissioner of the
nature and amount of the relevant item. Sec. 6501(e)(1)(A)(ii).
The question of whether the taxpayer adequately disclosed an item
on the return is a factual question. Whitesell v. Commissioner,
90 T.C. 702, 707-708 (1988).
The purpose of extending the period of limitations under
section 6501(e) is to level the playing field when the taxpayer’s
omission of income places the Commissioner at a disadvantage in
discovering errors. Colony, Inc. v. Commissioner, 357 U.S. 28,
36 (1958). Interpreting a prior version of section 6501(e), the
Supreme Court stated that Congress extended the period of
limitations to allow the Commissioner additional time “to
investigate tax returns in cases where, because of a taxpayer’s
omission to report some taxable item, the Commissioner is at a
special disadvantage in detecting errors. In such instances the
return on its face provides no clue to the existence of the
omitted item.” Id. To adequately apprise the Commissioner, “The
statement must be sufficiently detailed to alert the Commissioner
and his agents as to the nature of the transaction so that the
decision as to whether to select the return for audit may be a
reasonably informed one.” Estate of Fry v. Commissioner, 88 T.C.
1020, 1023 (1987). While a taxpayer’s disclosure must be more
substantial than supplying the Commissioner with “a ‘clue’ which
would be sufficient to intrigue a Sherlock Holmes”, the
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