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Jack, King of the Casinos, keeps learning the 2026 rules the hard way, and his CPA keeps explaining them. Each film links to the answer page that states the rule with its sources.
General information, not tax advice. New films on YouTube @W2gMatch.
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.
The fact behind the joke, and the transcriptThe 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.
The fact behind the joke, and the transcriptLas 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.
The fact behind the joke, and the transcriptEpisode 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.
The fact behind the joke, and the transcriptJack 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.
The fact behind the joke, and the transcriptJack 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.
The fact behind the joke, and the transcriptJack 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.
The fact behind the joke, and the transcriptEvery W-2G matched to the transcript and the statements, in one workpaper. First client file free.
For CPA firmsCreators and media: the films are free to share, clip and play on air, with downloads in the partner kit.
Free on every account
Say it
Speak or type the night. The AI box fills the entry.
Pick the place
One tap finds the casino near you and your players card.
Snap the W-2G
It reads the form and files it to the right tax year.
Your sessions, places and W-2Gs are filed as you go. At tax time, hand it off: the assistant reconciles them with your casino statements and IRS transcript in one file.