Lee B. Arberg and Melissa A. Quinn - Page 16




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          Whether to permit such an amendment to conform pleadings to the             
          evidence is a matter within the sound discretion of the Court.              
          E.g., Commissioner v. Estate of Long, 304 F.2d 136, 142-144 (9th            
          Cir. 1962); Estate of Quick v. Commissioner, 110 T.C. 172, 178              
          (1998); Bhattacharyya v. Commissioner, T.C. Memo. 2007-19.  It is           
          well settled both that amendment under Rule 41 may be allowed at            
          any time in a Tax Court proceeding through entry of decision and            
          that an affirmative defense may properly be pleaded through the             
          vehicle of a motion to conform under Rule 41(b)(1).  E.g.,                  
          Commissioner v. Finley, 265 F.2d 885, 888 (10th Cir. 1959), affg.           
          O’Shea v. Commissioner, T.C. Memo. 1957-15 and T.C. Memo. 1957-             
          16; LeFever v. Commissioner, 103 T.C. 525, 538 & n.16 (1994),               
          affd. 100 F.3d 778 (10th Cir. 1996); Stromsted v. Commissioner,             
          53 T.C. 330, 340 & n.5 (1969); Pierce v. Commissioner, T.C. Memo.           
          2003-188.                                                                   
               The touchstone in evaluating whether to allow an amendment             
          to conform pleadings to the evidence is the existence of unfair             
          surprise or prejudice to the nonmoving party.  E.g., Foman v.               
          Davis, supra at 182; Estate of Quick v. Commissioner, supra at              
          178-180; Kroh v. Commissioner, 98 T.C. 383, 387-389 (1992);                 
          Markwardt v. Commissioner, 64 T.C. 989, 998 (1975); Bhattacharyya           
          v. Commissioner, supra; Pierce v. Commissioner, supra.  Such                
          surprise or prejudice, in turn, rests largely on evidentiary and            
          other considerations bearing on the nonmovant’s opportunity to              







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