The Milwaukee Bucks are in a complex situation regarding Khris Middleton, given how much money they owe him in the next few years, so much so that his current contract is listed as one of the worst NBA deals this upcoming season.

According to Eric Pincus of Bleacher Report, the Milwaukee Bucks “overinvested” in Middleton by giving him nearly a $100 million extension last year because of his declining production.
“The Bucks may not have the right makeup of players to win another title despite boasting top-end talent like Giannis Antetokounmpo and Damian Lillard. Middleton was a huge part of the team’s 2021 title, but he hasn’t been at full strength the last couple of years,” Pincus wrote.

“By no means is he a bad player (quite the opposite), but Milwaukee is overinvested in Middleton as their third-best player when he hasn’t been able to be that on a day-to-day basis for the past 1-2 years,” he added.
Khris Middleton signed a three-year, $102 million deal in 2023, with $93 million fully guaranteed and another $9 million in bonus incentives. He will earn roughly $31.7 million in 2024-25 and has a $34 million player option in 2025-26 before becoming an unrestricted free agent in the summer of 2026.
Khris Middleton plans to shed “injury-prone” label with the Milwaukee Bucks
The Milwaukee Bucks haven’t lived up to their playoff contender status due to injuries to their key players, including Khris Middleton. Last season, the three-time NBA All-Star only averaged 15.1 points, 4.7 rebounds, and 5.3 assists on 49.3 percent shooting from the field in 55 regular season appearances.

Middleton underwent surgeries to fix his ankles in the offseason, and according to him, he is fighting his way back to 100 percent fitness to help his team.
“I take a lot of pride in taking care of my body since day one that I’ve been here. So, no, I don’t think I’m injury-prone at all,” Middleton said in an interview with The Athletic’s Eric Nehm. “I’ve just had unfortunate incidents that have happened on the basketball court, which is a wrong place, bad time type of thing.”
