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estopped from relitigating the factual determinations
that the Petitioner controlled Aldergrove partnership
matters in 1991 and that the Petitioner benefitted from
and controlled the funds in the Aldergrove account in
1991.
Although respondent's affirmative defense is broad in one
respect, see supra note 5, respondent restrictively frames the
issue that respondent seeks to preclude petitioners from
relitigating. Since respondent directs our analysis of that
affirmative defense to the facts relating to 1991 and also bears
the burden of proving the applicability of the defense, we must
assume that respondent does not seek to preclude petitioners from
relitigating this Court's findings in Monahan I regarding
petitioner's relationship with Aldergrove and other entities
prior to 1991 (the pre-1991 issues).
(2) The Authority of This Court To Raise Issue
Preclusion Sua Sponte
Issue preclusion is an affirmative defense that must be
pleaded, Rule 39, otherwise, it is deemed to be waived. See,
e.g., Jefferson v. Commissioner, 50 T.C. 963, 966-967 (1968).
Whether a party is precluded from relitigating an issue requires
particularized analysis, and, thus, respondent must be deemed to
have waived the defense of issue preclusion with respect to the
pre-1991 issues even though respondent has properly raised that
defense with respect to the Aldergrove issue. This Court,
however, need not always accept waivers of the defense of issue
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