Someone with more knowledge of the U.S. tax code than me will be able to explain how he's going to achieve this while funding a new corporation (perhaps he'll s

Someone with more knowledge of the U.S. tax code than me will be able to explain how he's going to achieve this while funding a new corporation (perhaps he'll set up a foundation that owns a corporation, similar to what some endowment funds do to avoid UBTI), but there is no way that he's going to make this gift much smaller by doing it in a way that realizes a taxable gain at the time of gift.