Dan Orlovsky loses brutal UConn-Michigan bet to Taylor Lewan

ESPN’s Dan Orlovsky, a proud UConn alum, had more on the line than just the national championship against Michigan Monday night.

Prior to the NCAA men’s basketball title game, Michigan alum Taylor Lewan proposed a friendly wager with Orlovsky. And because Michigan won, Orlovsky now needs to wear a dangle earring with a block M for one full month during every one of his media appearances. If UConn won, Lewan would have needed to dye his hair Husky blue.

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

It’s not the most exciting friendly bet ever, but it sure beats the time former New York mayor Eric Adams attempted to wager a vegan cheesecake with Philadelphia’s mayor ahead of the Divisional Round playoff matchup between the Giants and Eagles a few years ago.

The real question is, why did Orlovsky agree to these terms? He has to wear the earring for an entire month, but Lewan would have only had to dye his hair once within a two-week period? Lewan could have dyed his hair Husky blue and had it washed out before his next media appearance. And with UConn entering the game as the underdog, Orlovsky should have been able to negotiate better terms.

Another Michigan alum, Adam Schefter, joined ESPN Radio’s Unsportsmanlike Tuesday morning, where he proudly reported the details of Orlovsky’s wager. Chris Canty, however, noted Dan Orlovsky infamously isn’t great at paying his bets, noting he took over a year to fulfill a lost wager with their morning radio show.

.@danorlovsky7 doesn’t have the best track record with paying off bets… @AdamSchefter @BussinWTB | @ZipRecruiter https://t.co/arz0ncAb0d pic.twitter.com/qRZNJoGAn7

— UNSPORTSMANLIKE (@UnSportsESPN) April 7, 2026

If Dan Orlovsky wants to take it, there’s an easy way out of this bet too. The contract never stated what month Orlovsky needs to show up to his media appearances with an “M” earring, it only says that if he misses a day, the timeline will restart. If he starts paying the wager today, that means Orlovsky is going to need to wear the earring for almost daily appearances on Get Up, First Take, NFL Live, and even the NFL Draft. But nothing in the “contract” prevents him from paying off the bet in July, when Orlovsky makes only a handful of media appearances, if any at all.