- 10 - nature of severance or retirement benefits to compensate her for past services for which she was undercompensated. In order for a payment to be deductible as compensation, it must have been made with the intent to compensate. See Paula Constr. Co. v. Commissioner, 58 T.C. 1055, 1058 (1972), affd. without published opinion 474 F.2d 1345 (5th Cir. 1973). This is a question of fact decided on the basis of all the facts and circumstances of the case. See id. at 1059. Further, we are mindful that transactions involving closely held corporations and their controlling shareholders demand close scrutiny. See id. at 1058. While the Pension Agreement does recite that Barbara “during many * * * years * * * accepted compensation at a rate substantially less than her services would have commanded on the open market” and that petitioner intends to “appropriately compensate” Barbara’s past service with a retirement pension, there is no other evidence in the record that Barbara’s compensation for past services was less than market rate or that the value of the payments provided in the Pension Agreement approximated the past undercompensation. Cf. Estate of Wallace v. Commissioner, 95 T.C. 525, 553-554 (1990) (taxpayer must show past undercompensation and that current payments remedy that undercompensation), affd. 965 F.2d 1038 (11th Cir. 1992); Avis Indus. Corp. v. Commissioner, T.C. Memo. 1995-434 (same). Indeed, the available evidence points to the contrary conclusionPage: Previous 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 Next
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