Brian Windhorst is uniquely qualified to analyze the Milwaukee Bucks’ decision to waive Damian Lillard in order to acquire Myles Turner.
Not only because of his vast experience covering the NBA, but because the Akron, Ohio, native is also a Cleveland Browns fan.
And there might not be a fanbase that’s better equipped to identify when a franchise is mortgaging its future for a short-term solution than the Dawg Pound is. After all, it was just three years ago that the Browns traded three first-round picks to acquire Deshaun Watson, who they proceeded to sign to an unprecedented fully guaranteed $230 million contract.
Originally, Watson’s contract was set to expire after the 2026 season, but Cleveland’s repeated restructuring of his deal has kept him on the Browns’ books even longer. And Windhorst sees some similarities between that and the Bucks’ decision to waive and stretch Lillard’s contract, which they still owe $113 million of.
“It’s a level of mortgage that really pro sports has never seen before,” Windhorst said on Wednesday’s episode of First Take. “As a Cleveland Browns fan, this is akin to what the Deshaun Watson contract was except for Deshaun Watson wouldn’t even be on the team anymore. Which is pretty much the way it is anyway, but that’s another story for another day.”
Brian Windhorst on the Bucks waiving Damian Lillard to acquire Myles Turner: “As a Cleveland Browns fan, this is akin to what the Deshaun Watson contract was except for Deshaun Watson wouldn’t even be on the team anymore. Which is pretty much the way it is anyway, but that’s… pic.twitter.com/msRdYWFFC3
— Awful Announcing (@awfulannouncing) July 2, 2025
Windhorst was referring to the reality that Watson appears unlikely to play another down for the Browns as he continues to recover from a torn Achilles — the same injury that Lillard suffered in the Bucks’ first-round playoff series loss to the Indiana Pacers in April. Another similarity: the Browns are owned by Jimmy Haslam, who is also a part of the Bucks’ ownership group.
As for Windhorst’s analysis, he’s clearly not a fan of Milwaukee’s decision, which will result in the team taking a $22.5 million cap hit in each of the next five years to pay off the remainder of Lillard’s contract. But he’s also sympathetic to the reality that the Bucks are doing everything they can to keep Giannis Antetokounmpo, a situation he views similarly to the Cleveland Cavaliers’ efforts to retain LeBron James in 2010.
Still, the comparison to the Watson deal speaks for itself, as it’s universally viewed as one of the worst — if not the worst — transactions in sports history. As Windhorst stated on Get Up earlier on Wednesday morning, the Bucks aren’t just robbing Peter to pay Paul; they are “robbing Peter’s 401K to pay Paul’s loan shark bill.”
Brian Windhorst on the Bucks waiving Damian Lillard to sign Myles Turner: “I think it’s robbing Peter’s 401K to pay Paul’s loan shark bill if you want my honest assessment of it.” pic.twitter.com/XWHXIgUFJV
— Awful Announcing (@awfulannouncing) July 2, 2025