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Middleton declined a $40 million player option for next season to become a free agent at the start of the summer.
Injuries have plagued Middleton since the 2022 playoffs, as he missed Milwaukee’s final 10 playoff games with a sprained MCL. Last season he required surgery on his left wrist, which sidelined him for the first 20 games of the 2022-23 season. He returned on December 2, 2022, playing in six of seven games before missing 18 straight games with a sore right knee.
Middleton, who turns 32 in August, had successful surgery on his right knee shortly after Milwaukee’s first-round exit in the 2023 playoffs. He averaged nearly 24 points and 6.2 assists in that series, a five-game losing streak for the Miami Heat.
In 2021-22, Middleton’s last fully healthy season, he averaged 20.1 points, 5.4 rebounds and 5.4 assists and was named to his third All-Star team.
Middleton spent 10 seasons with the Bucks, transitioning from role player to All-Star and one of the faces of the franchise alongside Giannis Antetokounmpo. He had several big playoff performances in 2021 en route to the team’s first title in 50 years and moved into seventh place on Milwaukee’s all-time scoring list.