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College BasketballFootballDan Orlovsky

Dan Orlovsky facing hilarious punishment for losing bet backing UConn

April 6, 2026 by Renzo Pocholo Salao • Comments
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Dan Orlovsky smiles

Dan Orlovsky was unexpectedly one of the biggest losers of how this year’s NCAA Tournament ended.

Orlovsky, a former UConn quarterback, made an unwise wager with Michigan alum Taylor Lewan. The two \ backing their respective alma maters in their very public bet ahead of Monday’s UConn-Michigan national championship clash.

Lewan shared the details of their bet on X just before Monday’s game tipped off.

“Michigan wins, Dan Orlovsky must wear a single dangle earring on the right side with a Michigan block M for 1 full month on all media sports or otherwise. IF he forgets a day, the month timeline restarts,” Lewan posted.

“If UConn wins, Taylor Lewan must dye his hair husky Blue once. Failure to do so within a two week period he must keep it husky blue for the rest of the calendar year.”

Contract details:

Michigan wins, Dan Orlovsky must wear a single dangle earring on the right side with a Michigan block M for 1 full month on all media sports or otherwise. IF he forgets a day, the month timeline restarts.

If UConn wins, Taylor Lewan must dye his hair husky… https://t.co/eTN0IjXHFE

— Taylor Lewan (@TaylorLewan77) April 7, 2026

Unfortunately for Orlovsky, Michigan pulled away Monday with a resounding 69-63 win, leading UConn throughout the entire second half. For his sake, hopefully Orlovsky gets to keep the earring after serving his punishment. Perhaps that could have some value on an episode of “Pawn Stars.”

It hasn’t been a good week for Orlovsky, who also got hammered for his take on Lamar Jackson that aged terribly.

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