https://www.w2gmatch.com/videos/90-percent-gambling-loss-rule-verdict https://www.w2gmatch.com/videos/90-percent-gambling-loss-rule-verdict.jpg The King of the Casinos vs. the 90% Gambling Loss Rule Jack, King of the Casinos, takes the stand: he won a million, he lost a million, so they're even. His own CPA, Penny, has the 2026 rule, and the ruling is short. Jack and Penny were first introduced as Larry and Diane, the names you may still see or hear in this film. General information, not tax advice. https://www.youtube-nocookie.com/embed/1PdCpPVXvpc 24 2026-10-05 yes no W2gMatch no 90% rule gambling losses gambling taxes 2026 One Big Beautiful Bill gambling phantom income tax comedy https://www.w2gmatch.com/videos/high-roller-nature-documentary-90-percent-rule https://www.w2gmatch.com/videos/high-roller-nature-documentary-90-percent-rule.jpg A Wildlife Crew Films a High Roller. His CPA Ruins the Shot. The High Roller: A Natural History. A wildlife crew observes him in his habitat. He keeps no records. The crew's rule is never to intervene. His CPA does not work for the crew. Jack and Penny were first introduced as Larry and Diane, the names you may still see or hear in this film. General information, not tax advice. https://www.youtube-nocookie.com/embed/ziAliN1e2TU 25 2026-10-05 yes no W2gMatch no gambling records session log 90% rule gambling losses win loss statement tax comedy https://www.w2gmatch.com/videos/cpa-matches-last-w2g-irs-transcript https://www.w2gmatch.com/videos/cpa-matches-last-w2g-irs-transcript.jpg A CPA Matches the Last W-2G Like It's a Title Game Las Vegas, 2:07 a.m. One W-2G left unmatched against the client's IRS transcript, and it gets called like the final seconds of a title game. Then Penny explains what the same night means in tax year 2026. Jack and Penny were first introduced as Larry and Diane, the names you may still see or hear in this film. General information, not tax advice. https://www.youtube-nocookie.com/embed/uwNT8g8nvRI 30 2026-10-05 yes no W2gMatch no W-2G IRS transcript CPA tax reconciliation 90% rule gambling losses accountant comedy https://www.w2gmatch.com/videos/week-in-gambling-ep-1-vegas-matt-mr-hand-pay-slot-queen https://www.w2gmatch.com/videos/week-in-gambling-ep-1-vegas-matt-mr-hand-pay-slot-queen.jpg Vegas Matt, Mr. Hand Pay, Slot Queen: The Week in Gambling (Ep. 1) with Jack and Penny Episode 1 of the weekly recap. Jack names the week: Vegas Matt at $500 a spin and $14,000 on the Don't, Mr. Hand Pay in Arizona, Slot Queen at craps, Stacey's red-screen run, Cowboy Slots, Low Budget High Limit, Gamble Smart, Unabated, PokerNews and Circles Off. Penny lands the tax line each moment carries, the two of them trade the board of wins and losses, and she leaves Jack three habits that keep more of a win. Then a preview of next Friday. Jack and Penny were first introduced as Larry and Diane, the names you may still see or hear in this film. General information, not tax advice. https://www.youtube-nocookie.com/embed/fzp6ambFaZA 134 2026-10-05 yes no W2gMatch no Vegas Matt Mr. Hand Pay Slot Queen Stacey's High Limit Slots Cowboy Slots Low Budget High Limit Slots Gamble Smart Unabated PokerNews Circles Off week in gambling slot machine jackpot handpay high limit slots gambling taxes W-2G win loss statement Jack and Penny The Week in Gambling https://www.w2gmatch.com/videos/fanduel-win-loss-statement-for-taxes https://www.w2gmatch.com/videos/fanduel-win-loss-statement-for-taxes.jpg FanDuel Win/Loss Statement for Taxes: Where to Find It (2025 & 2026) Jack asks where his FanDuel win/loss statement is; Penny names it, the Player Activity Statement, and gives the route: Your Play, Activity Statement, set January 1 to December 31, Download Statement. It is not a tax form, and FanDuel does not send it to the IRS; the W-2G and 1099 PDFs are separate, in the Tax Center. Then the free session tracker every account gets. General information, not tax advice. https://www.youtube-nocookie.com/embed/8nNU256b7UQ 41 2026-10-05 yes no W2gMatch no FanDuel win loss statement FanDuel taxes FanDuel player activity statement FanDuel W-2G sportsbook taxes gambling taxes 2026 Jack and Penny https://www.w2gmatch.com/videos/caesars-rewards-win-loss-statement https://www.w2gmatch.com/videos/caesars-rewards-win-loss-statement.jpg How to Get Your Caesars Rewards Win/Loss Statement Jack asks where his Caesars Rewards win/loss statement is. Penny's route: sign in at caesars.com, choose Win/Loss Statement, accept the terms and click Generate, with pop-ups allowed. The statement covers play on the Caesars Rewards card, so card in every visit. Then the free session tracker every account gets. General information, not tax advice. https://www.youtube-nocookie.com/embed/9KUnaiJorb4 32 2026-10-05 yes no W2gMatch no Caesars Rewards win loss statement Caesars win loss statement Harrah's win loss statement casino win loss statement W-2G Jack and Penny https://www.w2gmatch.com/videos/kalshi-taxes-which-1099 https://www.w2gmatch.com/videos/kalshi-taxes-which-1099.jpg Kalshi Taxes: Which 1099 Do You Get? Jack asks which 1099 a prediction market sends. Penny: for event contract gains, none, and they are still taxable. The narrator lists the forms Kalshi does send: 1099-MISC for rewards, 1099-INT for interest, 1099-B or 1099-DA for some crypto. Keep the PnL statement; the IRS has not said how event contracts are taxed. Then the free session tracker every account gets. General information, not tax advice. https://www.youtube-nocookie.com/embed/1pZXcmVuZcc 41 2026-10-05 yes no W2gMatch no Kalshi taxes Kalshi 1099 prediction market taxes Polymarket taxes event contracts taxes 1099-DA Jack and Penny