Gary Kondler on taxes for gamblers

Bob and Richard sit down with Gary Kondler to talk about taxes for gamblers after the big beautiful bill. It may not be as bad for some of us as we all thought. Spoiler alert - but some gamblers are just screwed. Show Notes [00:00] Introduction of gambling tax expert Gary Kondler from Kondler & Associates [01:36] W2Gs under the new tax law [05:24] Reconciling W2s with session win/loss [09:43] An example of casino gambling profit and discussion of similar case law [18:04] Sports betting example [20:46] Could a day of betting across different sportsbooks be considered a single session? [24:28] Arbitrage bettors versus poker players [27:06] What type of gambler would benefit from creating an S corp [30:00] Casino generated win/loss statements [31:54] Should clients file on time or file an extension? [37:49] IRS layoffs [40:57] How can listeners contact Gary? [42:45] Brian Camp’s legal opinion [44:55] Kalshi and other predictive markets [47:48] Professional versus non-professional gambler [51:34] Does filing with losses affect the professional gambler classification? Links: Kondlercpa.com

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Gary Kondler on taxes for gamblers is an episode from Gambling With an Edge by Bob Dancer & Richard Munchkin.

This episode is 54:35 long.

This episode was published on Dec 25, 2025.

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