Middleton averaged 15.1 points (44/32/90 shooting splits), 4.9 assists and 4.2 rebounds in just 24.3 minutes over 33 games for the Bucks this past season. He missed the first 20 games of the year due to offseason surgery on his left wrist and another 18 games over the winter with a sore right knee, which required arthroscopic surgery after Milwaukee's disappointing first-round playoff loss to the Miami Heat.
A sprained left MCL also cost Middleton the final 10 games of the 2022 playoffs, when the defending champion Bucks lost a seven-game series to the Boston Celtics in the Eastern Conference semifinals.
Prior to his recent string of injuries, Middleton was the silent assassin to two-time NBA MVP Giannis Antetokounmpo's flame-throwing supernova, averaging a 20-6-5 on 46/39/88 shooting splits over a five-year span from 2017-22 that included three All-Star nods. Middleton averaged 23.6 points (44/34/89 splits), 7.6 rebounds and 5.1 assists in 40.1 minutes per game on Milwaukee's 2021 run to the title.
"Khris is core to who we are and really all the success we've had,” Bucks general manager Jon Horst said during his post-draft news conference. "Our goal is always to sustain our success and continue to compete and have a chance to win and be in position to win, year in and year out. We hope to have him back."
Middleton turns 32 years old in August and declined a player option for the final season of the five-year, $177.5 million maximum contract he signed with the Bucks in 2019. That decision signaled some urgency to secure another high-paying deal before his current trend of injuries could phase him into another chapter of an 11-year career that began as a Detroit Pistons' second-round draft pick out of Texas A&M in 2012.
The concern is that Middleton has already entered another phase of his career. The Bucks had to weigh that against the championship desires of Antetokounmpo, who is two years from his own player option and could grow frustrated with Milwaukee's intertwined roster-building and financial decisions at any time.
In the weeks leading up to their title victory together, Antetokounmpo told Middleton, "The day you retire is going to be the toughest day in my career because I've been with you the whole time, and it’s been an unbelievable journey." Antetokounmpo and Middleton have been together since joining the Bucks in 2013.