Gambling Twitter Explodes • DraftKings Co-Founder RANT • UFC Tax Push | Circle Back

Gambling Twitter Explodes • DraftKings Co-Founder RANT • UFC Tax Push | Circle Back

May 21, 2026 · 1h 14m

About this episode

The episode discusses a viral rant by DraftKings co-founder Matt Kalish and its implications for the gambling industry.

DraftKings co-founder Matt Kalish set Gambling Twitter on fire after a viral rant about prediction markets, sharp bettors, retail gamblers, and the future of sports betting. Jacob Gramegna, Joey Knish, Storm Pig, and Porter of BA Analytics react to the entire situation, break down the backlash, and discuss what the conversation says about the current state of the gambling industry. The crew also dives into the viral “Sports betting will be dead in 5-10 years” take, whether traditional betting research still works, and why so many bettors feel the space is changing rapidly. The show also covers Dana White asking President Donald Trump to help reverse the 90 percent limit on gambling loss deductions for US taxpayers, why the gambling tax issue has become a major talking point across the industry, and plenty more betting discourse from the week. Circle Back LIVE airs every Thursday at 4 PM ET on Circles Off, part of The Hammer Betting Network, hosted by Jacob Gramegna with rotating guests from the sports betting and analytics space. 📅 New episodes of Circle Back LIVE every Monday at 1 pm ET and Thursday at 4 pm ET. Plus, watch for additional content every Wednesday, ranging from…

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