After Mary’s death, her executor filed an estate tax return which described Peter’s signed acknowledgement as a “[p]romissory note dated May 3, 1995, in the face amount of $771,628” that “is wholly uncollectible and worthless” because “Peter P. Bolles is insolvent.” The estate tax return also failed to report the additional amounts transferred to or for Peter’s benefit as gifts made to him during Mary’s life. After reviewing the estate tax return and the history of payments, the Internal Revenue Service disputed how the transfers from Mary to Peter were reported on the return and sent Mary’s executor a notice of deficiency, claiming: (1) if any amounts were loans, the return needed to account for any outstanding amounts by adding them to the gross estate, and (2) if any amounts were gifts, the return would need to reflect such amounts as “prior gifts.” As the parties were unable to come to an agreement as to which payments were loans and which payments were gifts, the executor resorted to the Tax Court to resolve the issue., The Tax Court held that because the note was properly structured and administered, the note was correctly characterized as a loan, and not a gift or partial gift/loan. The Tax Court granted summary judgment for the nonpayment of gift tax and granted partial summary judgment for the underpayment of estate tax. Takeaways. Barbara Galli v., In a recent tax court case, Estate of Bolles v. Commissioner, T.C. Memo. 2020-71, 119 T.C.M. (CCH) 1502 (June 1, 2020), the court recognized that where a family loan is involved, an actual expectation of repayment and an intent to enforce the debt are crucial for a transaction to be considered a loan. Many people use trusts and gifts as estate .