Khris Middleton Milwaukee Bucks
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Khris Middleton is re-signing with the Milwaukee Bucks for three years and $102 million, according to ESPN's Adrian Wojnarowski. Middleton, who spent his rookie season with the Detroit Pistons but has been a Buck ever since, declined a $40 million player option earlier in the offseason in order to give himself the choice to explore free agency. However, his return to the Bucks was never really in doubt. He was reportedly a part of the meetings that led to Adrian Griffin being hired as Milwaukee's head coach, and now, he will return to the team that helped him become a star.

Middleton came into the league as a wing with 3-and-D upside, but over time, he grew into one of the best all-around forwards in basketball. He made three All-Star teams with the Bucks, but more importantly, he served as Milwaukee's late-game shot-creator during their run to the 2021 championship. 

Teammate and friend Giannis Antetokounmpo won Finals MVP for his work in that series, but publicly praised Middleton as his long-time co-star from the podium. With Antetokounmpo eligible for an extension this offseason, keeping Middleton was essential for Milwaukee as it hopes to convince arguably the best player in the world to stay with the Bucks.

However, a long-term commitment to Middleton isn't without its risks. Middleton suffered an MCL injury in the first round of the 2022 postseason against the Chicago Bulls. He didn't return, and Milwaukee lost a seven-game heartbreaker to the Boston Celtics. He struggled to get healthy last season, averaging 15.1 points in 33 games for the Bucks. Middleton will turn 32 this offseason, and his long-term durability is far from a sure thing.

But Middleton managed to average 23.8 points per game in Milwaukee's first-round loss to the Miami Heat, and more importantly, the salary cap essentially prevented the Bucks from adequately replacing him if he had left. The Bucks had the NBA's best record last season, and keeping that roster together was a priority as they pursue their second championship with this core. Now, their All-Star forward's future in Milwaukee has been assured.