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ATLANTA, GA – OCTOBER 13: ESPN analyst Dan Orlovsky reacts prior to the start of the NFL, American Football Herren, USA game between the Buffalo Bills and the Atlanta Falcons on October 13th, 2025 at Mercedes-Benz Stadium in Atlanta, GA. Photo by Rich von Biberstein/Icon Sportswire NFL: OCT 13 Bills at Falcons EDITORIAL USE ONLY Icon251013176
Imago
ATLANTA, GA – OCTOBER 13: ESPN analyst Dan Orlovsky reacts prior to the start of the NFL, American Football Herren, USA game between the Buffalo Bills and the Atlanta Falcons on October 13th, 2025 at Mercedes-Benz Stadium in Atlanta, GA. Photo by Rich von Biberstein/Icon Sportswire NFL: OCT 13 Bills at Falcons EDITORIAL USE ONLY Icon251013176
When the Michigan Wolverines were set to face the UConn Huskies in the final of the 2026 NCAA Men’s Basketball Tournament, there was more than just a national title on the line for UConn alum and ESPN analyst Dan Orlovsky. He had already put himself in a spot. A wager with Michigan alum Taylor Lewan meant that if the Huskies lost, Orlovsky would have to wear a dangling earring featuring Michigan’s block “M.” Now that the result is in, there is no wiggle room. Orlovsky has to follow through.
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“Dan Orlovsky now has to wear a clip-on dangling Michigan earring for the next month on every show he appears,” ESPN’s Adam Schefter, who is also a Michigan alum, shared the news on X. “If he misses a day, it starts over.”
Dan Orlovsky now has to wear a clip-on dangling Michigan earring for the next month on every show he appears.
If he misses a day, it starts over. pic.twitter.com/dhBj2B1eXo
— Adam Schefter (@AdamSchefter) April 7, 2026
The bet itself had picked up traction in the days leading up to the title game. Lewan laid out the terms clearly. If Michigan lost, he would dye his hair husky blue.
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If UConn lost, Orlovsky would wear a single dangling earring on the right side with Michigan’s logo for a full month across all his media appearances. The reset clause only made it tougher. Miss one day, and the clock goes back to zero.
Even before the game, Orlovsky did not sound fully convinced.
“I’m cautious,” Orlovsky had said before the game. “I’m cautious on it. I’m cautious to accept.”
That hesitation now looks justified. Michigan, the No. 1 seed, took down No. 2 UConn 69-63 and secured its first title since 1989. With that, the outcome of the bet became official. Orlovsky lost, and the terms are no longer hypothetical.
Which brings up the obvious question. Why take the bet in the first place? And now that he has lost it, the bigger question follows naturally. Will he actually go through with it? At least one person is already not convinced that Orlovsky will fully commit to paying off the wager.
Chris Canty believes Dan Orlovsky isn’t great at paying his bets
Once the wager between Dan Orlovsky, who’s recently been under the spotlight, and Taylor Lewan was settled, Adam Schefter joined ESPN Radio’s Unsportsmanlike on Tuesday morning. Speaking with Chris Canty, Schefter, himself a Michigan alum, leaned into the moment and laid out the details of Orlovsky’s bet proudly. Canty, though, added a layer of skepticism right after Schefter finished.
“I will just say this, Dan Orlovsky doesn’t have the best track record when it comes to paying off bets,” Canty told Schefter. “It took him over a year before he paid off a bet with us.”
That naturally brings up the next question. Will Orlovsky actually follow through this time? For now, it is still uncertain. But context matters here. If he starts paying off the wager immediately, he is looking at wearing the earring across near-daily appearances on Get Up, First Take, NFL Live, and even around the NFL Draft.
At the same time, there is a small technical window. The bet never specifies which month the punishment has to be served. That detail could give Orlovsky some flexibility. In theory, it allows him to delay it until a lighter schedule, like July, when his media appearances are far less frequent.
So the situation remains open-ended. Whether Orlovsky pays up now or finds a way to push it down the calendar could end up being a telling moment in how this story unfolds across his media appearances.
