Gambling With an Edge Gary Kondler on taxes for gamblers
Dec 25, 2025
Gary Kondler, a gambling tax expert and CPA, shares insights on navigating the complex landscape of gambling taxes after new law changes. He explains why the recent tax bill might not be as disastrous as many feared, discussing strategies for tracking W-2Gs and reconciling session wins with totals. Gary highlights when creating an S corp can be beneficial for gamblers and warns about the unreliability of casino-generated win/loss statements. He emphasizes the importance of meticulous recordkeeping to avoid audit triggers and provides advice on filing strategies.
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Reconcile W-2Gs Early
- Do track your W-2G total and reconcile it with IRS wage-and-income transcripts after June.
- Use ID.me to download transcripts and amend returns if necessary to avoid audit flags.
Keep Session Records Tied To W-2Gs
- Do record session-level wins and losses and keep disclosure statements tying them to W-2Gs.
- Use court-case methods to report true net income while documenting the W-2G gross total.
10% Reduction Applies To Sessions
- The 10% reduction from the new law can be applied to session-method losses, not necessarily W-2G totals.
- Use Stallenberger to calculate reductions on summed session losses rather than gross receipts.