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 Larry, King of the Casinos, takes the stand: he won a million, he lost a million, so they're even. His own CPA, Diane, has the 2026 rule, and the ruling is short. Fictional characters. AI-generated video. 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. Fictional characters. AI-generated video. 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/tax-deadline-napkin-records https://www.w2gmatch.com/videos/tax-deadline-napkin-records.jpg His Last Text Before the Tax Deadline Was His Entire Tax Records 11:58 PM, October 15. Larry, King of the Casinos, sends his CPA everything she needs: one photo of a cocktail napkin. Diane's team takes it as seriously as it deserves. Fictional characters. AI-generated video. General information, not tax advice. https://www.youtube-nocookie.com/embed/dMS0uHX60vQ 30 2026-10-05 yes no W2gMatch no tax deadline October 15 extension gambling records W-2G win loss statement CPA humor 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 Diane explains what the same night means in tax year 2026. Fictional characters. AI-generated video. 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 Larry and Diane Episode 1 of the weekly recap. Larry 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. Diane lands the tax line each moment carries, the two of them trade the board of wins and losses, and she leaves Larry three habits that keep more of a win. Then a preview of next Friday. Fictional characters. AI-generated video. 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 Larry and Diane The Week in Gambling