Despite Paul Pierce’s ’20 Mile’ Regret, Ex-NBA Star Doubles Down on Celtics With Bold Luxury Wager

Ever felt the sting when your arrow spins around and hits you right back? Hurts the ego, doesn’t it? That’s probably what Paul Pierce’s dealing with right now. The guy flexed hard on his Boston Celtics, making a bold bet before Game 2 against the Knicks. Now, guess who’s walking the same risky path? It’s Chandler Parsons.

Paul Pierce went all in on his Boston Celtics before Game 2 against the New York Knicks. The former Celtics star showed wild confidence, betting big on his squad during FS1’s Speak. Sadly for Pierce, the Celtics came up short again, dropping a nail-biter 91-90 at home. And man, it left Pierce in an awkward, regrettable spot after the final buzzer. Before tipoff, he made a bold promise that quickly came back to haunt him. “If the Celtics lose Game 2 at home, I promise you, I’m walking here tomorrow, 15 miles. I’m walking here. In my robe, no shoes on, barefoot… I’m telling you right now.” Pierce added confidently. Safe to say that aged like milk.

To top it off, the distance from Pierce’s house to the studio is actually 20.2 miles. Yeah,  let’s hope his feet survive that barefoot trip. Now, Chandler Parsons is stepping into the same mess Pierce did, just with a shinier wager. This time, it’s not a 15-mile walk. It’s a luxury watch on the line. On a recent Run It Back podcast episode, Parsons made a bold call about the Knicks-Celtics series. “I’d be more surprised at a sweep or gentleman’s sweep for the Knicks than the Boston Celtics winning 4-straight and winning in 6,” Persons said. 

Right now, the Knicks are sitting comfortably with a 2-0 lead in the series. Host Michelle Beadle wasn’t buying that take and tossed a playful challenge Parsons’ way. “Would you like to put a friendly wager on that?” she asked, raising the stakes for the conversation. The prize?  “One of your watches vs something I pick out of my house.” Beadle proposed with a grin. Parsons didn’t back down, and the two sealed the bet with a virtual handshake.

“I’d be more surprised at a sweep or gentleman’s sweep for the Knicks, than the Boston Celtics winning 4-straight and winning in 6.”

Chandler Parsons is betting Michelle Beadle one of his watches on the outcome of this series @MichelleDBeadle | @TeamLou23 | @ChandlerParsons pic.twitter.com/VNHA8azkUo

— Run It Back (@RunItBackFDTV) May 8, 2025

Now, fans are hyped to see how this bet plays out. Will Parsons’ bold prediction pay off with a Celtics comeback and six wins? Or will he, like Paul Pierce, pay the price for getting a little too cocky? Only time and a few playoff games will tell.

Paul Pierce Signals He’s Ready to Pay the Price for His Bold Challenge

To his credit, Paul Pierce didn’t back down from his bold promise. After the Celtics’ heartbreaking one-point loss at home, most people expected him to quietly let it slide. But no, Pierce actually followed through and took fans along for the entire ride.

He fired up his Instagram story early in the morning, ready to start his dreaded 15-mile walk. Now, he did fudge the details a little. Pierce originally claimed he’d hit the road at 3 a.m., but that didn’t exactly happen. Instead, around 5 a.m. PT, the former Celtics star posted a video of himself leaving his house.

And yes, just like he promised on Speak, he was wearing a robe with no shoes. Looking half-asleep and already regretting his life choices, Pierce told fans he’d check in throughout the journey. From there, he stayed true to his word, sharing multiple updates as he made his long, painful trek. The videos showed him walking through empty streets, probably questioning every decision that led him to this bet.

Pierce even cracked jokes, trying to keep his spirits up as the miles dragged on. To be fair, credit where it’s due, a lot of people talk big, but few actually follow through. Say what you will about Pierce’s prediction, but the man owned up to his mistake in the most hilarious way possible.

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