Platinum Tax Defenders: Since the IRS raised the annual gift tax .com/ sites / deborahljacobs //03/22/ dont - gamble-with-gift - tax - returns). Deborah L. Jacobs, a tax attorney and writer at Forbes, explains: property as he or she wishes to a spouse without triggering the gift tax. still working on our tax returns don't miss the Oct. 16 extended deadline. April 18 calendar page; click image to go to IRS website "The Gambler's Guide to Taxes. And yes, I claim my winnings on my tax return. "If I gamble online, it's overseas, and I don't have to pay tax on it. . of the material in this article is based on an article I wrote for Chuck Humphrey's excellent website, Gambling jeffok.com.