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restructure the transaction with the benefit of hindsight in
applying the substance over form doctrine. Id. at 542; see also
Commissioner v. Natl. Alfalfa Dehydrating & Milling Co., 417 U.S.
134, 149 (1974) (“while a taxpayer is free to organize his
affairs as he chooses, nevertheless, once having done so, he must
accept the tax consequences of his choice, whether contemplated
or not, * * * and may not enjoy the benefit of some other route
he might have chosen to follow but did not”); Estate of
Rosenblatt v. Commissioner, T.C. Memo. 1977-12 (“We cannot treat
lightly the formal manner in which properties are held, lest we
subject legal titles to unnecessary uncertainties and complicate
the administration of law.”).
The estate has not produced sufficient credible evidence to
show that the ownership of the property is different from the
form set forth in all the relevant documents and, therefore, has
not proved that the substance of the transaction was different
from its form. The evidence offered on the estate’s behalf is
Joseph S. Maniglia’s testimony and that of his spouse and his
accountant. At trial, Joseph S. Maniglia stated that “Every real
estate broker on Charles Street in Boston knew I was one of the
owners of that building.” We agree that, as the trustee of the
Fam-Trust, Joseph S. Maniglia would be the legal holder of title
to the property. However, the estate does not appear to
appreciate the fact that as trustee, Joseph S. Maniglia would
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