Gary Kondler on taxes for gamblers

Gary Kondler on taxes for gamblers

From Gambling With an Edge by Bob Dancer & Richard Munchkin

December 25, 2025 · 55 min

About this episode

Bob and Richard discuss gambling taxes with expert Gary Kondler, exploring the implications of recent tax laws 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…

People in this episode

Hosts: Bob Dancer, Richard Munchkin

Guest: Gary Kondler

Topics covered

  • gambling taxes
  • W2Gs
  • sports betting
  • professional gamblers
  • S corp benefits
  • IRS regulations

Keywords

  • gambling taxes
  • W2G
  • session win/loss
  • sports betting
  • S corp
  • professional gambler
  • IRS

Mentioned in this episode

Organizations: Kondler & Associates, IRS, Kalshi, Tax Notes

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