Projecting Khris Middleton’s Next Contract With Milwaukee Bucks

After filling the open head coach position, determining how to retain Khris Middleton’s services is second on the Milwaukee Bucks’ offseason to-do list.

By now, you probably know he has a $40.4 million player option for the 2023-24 season. An option he must make a decision on by June 21st. There are basically five choices he and the Bucks have:

1. Accept the player option and play the season on a one-year deal (unlikely)
2. Accept the player option and sign a contract extension of up to four years and $220.6 million (a $55.15 million average salary)
3. Decline the player option and sign with a new team in free agency
4. Decline the player option and re-sign (this would happen on or after July 1st and be worth up to five years and $272 million)
5. Decline the player option and sign an extension (this would happen on or before June 30th and be worth up to four years and $204 million with the caveat that 2023-24 couldn’t be for less than the option he declined)

His play and injury situation further complicates the situation. He’s coming off his worst statistical season since the Bucks’ rise to prominence in 2018, averaging 15.1 points, 4.2 rebounds and 4.9 assists per game while posting a measly 49.9 percent effective field goal percentage.

He showed flashes of his old self, especially in the postseason when he bookended their upset loss with 33-point performances. However, he also put up a couple of stinkers during the series, displaying signs of struggling to handle and shoot the ball.

The inconsistency he showed throughout 2022-23 is a major concern for a 31-year-old looking for another big payday on a multi-year contract.

Of course, I’d be remiss if I didn’t mention the injuries he was battling last year as well. It seems to stem from the 2022 All-Star break when Middleton initially hurt his wrist. He reportedly played through that pain before suffering an injury to his left knee against the Chicago Bulls in last year’s playoffs. That forced him to miss the final three games of the series and the entire semi-final round against the Boston Celtics.

In the offseason, Middleton decided to address both the knee and the wrist issues, putting him on the shelf for most of the summer. He didn’t make his season debut until December 2nd, but only lasted seven games before being unable to play due to his left knee.

After sitting out for another five weeks, he returned on January 23rd and slowly worked his way back into game shape. With Milwaukee being extremely cautious with him, he didn’t play 30 minutes in a single game until March 7th and never played in a back-to-back.

In a game against the Bulls on April 5th—just days before the end of the regular season—he landed awkwardly on his right knee and was unable to finish the game. This was the knee he historically had issues with dating back to college (other than his playoff injury last year). There were questions about his postseason availability and how much he could help the Bucks in the first round. In 34.6 minutes per game, he averaged 23.8 points, 6.4 rebounds and 6.2 assists per game while shooting a 54.1 percent effective field goal percentage.

That postseason push may have reinstilled some confidence in the Bucks’ organization.

If Middleton leaves in free agency, Milwaukee won’t suddenly have $40 million to spend in free agency or on other players. Due to their position with the luxury cap, that’s lost money that walks out the door when he does.

He may not be worth anything close to that much anymore, but Milwaukee is backed into a corner. Their best shot at winning a title next year is to bring back the same core, hire a coach with a fresh perspective and make some tweaks to the role players.

Giannis Antetokounmpo is under contract for two more years with a player option for the 2025-26 season. Jrue Holiday has a player option that runs through the 2024-25 season. It makes sense to also bring Brook Lopez back on a deal that runs through the 2024-25 season. Do you see what I’m getting at with Middleton?

The best path forward for both sides may be to add an extra year of protection for Middleton while negotiating the amount of annual money down from the current $40.4 million. Doing it this way means he would have to hit unrestricted free agency on July 1 before re-signing with the Bucks.

Contract Projection: Three years for $90 million with a player option on the third year