Dave Portnoy should stick to his day job after this March Madness shot

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Prior to tip-off between Illinois and Houston in the Sweet 16, Dave Portnoy, the founder of Barstool Sports and arguably the biggest sports personality there is, was captured taking what looked like the worst shot to ever be taken on a March Madness court.

Portnoy and other Barstool Sports personalities, including “Big Cat,” were seen putting shots up before the game, all of which should’ve been left unseen.

Outside of his broken shot, Portnoy has bigger things to worry about when it comes to March Madness with his alma mater, Michigan, tipping off against Alabama in the Sweet 16 on Friday Night.

Illinois vs Houston pic.twitter.com/3PDqiZHXA8

— Barstool Sports (@barstoolsports) March 27, 2026

More: Can Purdue make it three years in a row of homecourt advantage in March Madness?

There is also a hefty wager on the line for Portnoy against one of his Barstool employees and Crimson Tide fan, Rico Bosco. If Alabama wins, the boss will double Bosco’s salary and give him a 10-year contract. If Michigan wins, Bosco will need to host a podcast with former Barstool personality Jeff Nadu, who gained notoriety for his rocky relationship with Bosco.

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