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This Court has looked to cases decided under rule 15(a) of
the Federal Rules of Civil Procedure for guidance on the
interpretation of Rule 41(a). Kramer v. Commissioner, 89 T.C.
1081, 1084-1085 (1987). Like Rule 41(a), rule 15(a) of the
Federal Rules of Civil Procedure mandates that leave to amend
"shall be given freely when justice so requires."
The decision of whether a motion to amend the pleadings
should be granted is within the sound discretion of the Court.
Zenith Radio Corp. v. Hazeltine Research, 401 U.S. 321, 330
(1971); Foman v. Davis, 371 U.S. 178, 182 (1962). The exercise
of our discretion, however, must be controlled by sound reason
and fairness. Law v. Commissioner, 84 T.C. 985, 990 (1985).
Petitioners maintain that Rule 39 requires a party to
include in his or her pleadings any matter consisting of an
avoidance or affirmative defense. The underlying rationale for
this Rule is to provide the opposing party ample opportunity to
address the related issues. There is no doubt that estoppel and
its various counterparts, such as quasi-estoppel and equitable
estoppel, are affirmative defenses within the meaning of Rule 39.
Petitioners, however, fail to properly consider Rule 41 or the
appellate mandate in this case. In appropriate circumstances we
may permit the movant to amend the pleadings so as to include a
previously omitted affirmative defense. See Flint v.
Commissioner, T.C. Memo. 1991-405; Lilley v. Commissioner, T.C.
Memo. 1989-602, affd. without published opinion 925 F.2d 417 (3d
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