Addressing the Uncertain Future of Khris Middleton

The Bucks’ 2022–23 season ended much earlier than many basketball fans anticipated, and with that premature exodus came some uncomfortable questions.

Obviously, the top priority is finding the replacement for recently-dismissed head coach Mike Budenholzer—and that search is narrowing as we speak. However, just below that, we get into the debate on Khris Middleton’s future with the squad.

By most accounts, Middleton has been the most valuable non-Giannis player in the current era of Bucks basketball. In his 10 seasons with the squad, he has tallied three All-Star appearances, and his 24 points per game in the 2021 NBA finals were pivotal to the Larry O’Brien Trophy returning to Milwaukee.

It’s also worth mentioning that Middleton has been paid handsomely for his efforts. He inked a five-year, $177.5 million contract ahead of the 2019–20 season. He is entering the final year of that deal, which has a player option. If he opts in, he will earn $40.4 million in the upcoming season.

Despite his notable contributions to the team, it makes sense that Milwaukee could be looking in another direction in the future. In the two playoff runs since the 2021 title, Middleton has not been a consistent Robin to Giannis’ Batman in terms of availability and performance. His age is also a factor, as he will be 32 the next time he steps on a basketball court.

With that said, let’s examine some potential scenarios for Middleton’s future:

Middleton stays

There are several reasons why it makes sense for the Bucks to keep Middleton around. First and foremost, he has a strong relationship with Giannis and the organization. Secondly, he has been a solid contributor to the team when healthy. Lastly, the Bucks’ cap situation makes signing a player capable of replacing Middleton’s production in free agency impossible.

There are ramifications if he stays too, though. If he opts in to the final year of his deal, the Bucks’ payroll would already be as high as $157.4 million with only eight players under contract. This would stretch the Bucks very thin in terms of filling out the rest of the roster, and the team runs a risk of losing Brook Lopez, who is an unrestricted free agent.

It is also possible that Middleton declines the player option. It seems unlikely that he will find a higher yearly salary on the open market, but crazier things have happened. Since he’s on the wrong side of 30, he could be looking for a deal that provides financial certainty for years to come. Milwaukee could still be in the works for an extension, but his yearly salary would likely take a hit compared to his current deal.

The Bucks find a trade partner

Middleton would be an appealing option for several teams. With the Bucks’ tight cap situation, they are definitely in a position to listen to offers.

Houston Rockets: For Middleton to opt in to the last year of his deal and be traded, a team would have to be willing to stomach his high salary and the possibility of him leaving in free agency in the 2023–24 offseason. This seems fairly unlikely, but a few teams have the financial chops to make a risky move like this. The Rockets have emerged as a team capable of this maneuver.

They have the most favorable cap situation in the league heading into next season, with 11 players under contract and a projected $65 million in available cap space. The Rockets have talented players like Jalen Green, Jabari Smith Jr., and Alperen Sengun who could be trade bait in a move like this. They also have the fourth overall pick in this year’s draft. After three dreadful tank-a-thon seasons, it makes sense for them to add a prominent veteran like Middleton as they enter the Ime Udoka era. A cocktail of youngsters—let’s say Green and Josh Christopher—or one plus the 2024 first-round pick that Houston acquired from Brooklyn seems like a relatively fair price. This trade would free up about $28 million in salary for the Bucks.

This situation is far from perfect for either party, though. While the Rockets have talent, calling their assets “young” would be an understatement. Hell, Houston’s roster has an average age of 22 years old (which could be even lower if they didn’t have 30-year-old Frank Kaminsky and 34-year-old Boban Marjanović on the bench). These players do not have experience playing winning basketball, and the Bucks are in a position to win now. Regardless of talent, blowing up the current lineup to pair Giannis with shot-chuckers who aren’t old enough to drink legally would be a massive risk.

Another issue that could stifle this trade would be pushback from Middleton. Although he does not have a no-trade clause, would Middleton want to leave a perennial contender like Milwaukee for an unfinished product like Houston? As bright as the future could be in the Space City, I wouldn’t hold my breath on that.

Indiana Pacers: If Middleton declines his player option, the Bucks would be in the position to execute a sign-and-trade, which would give them more realistic trade partners. One of these prospects is the Indiana Pacers.

Given Milwaukee’s needs, it feels almost guaranteed that a trade involving the Pacers would include Buddy Hield. He’s overpaid sure, but he has a career 3-point percentage north of 40 and has been a rumored trade piece for the last year. A package including Hield, a 2023 first-round pick, and two role players—in this case, bigs Daniel Theis and Isaiah Jackson—would free up $9.3 million in salary and give the Bucks some much-needed depth at the center position.

This trade is possible, but it runs into a few of the same problems as the Houston hypothetical. Firstly, this scenario requires Middleton to be willing to leave Milwaukee for Indiana. A lineup featuring Middleton, Tyrese Haliburton, Myles Turner, and Bennedict Mathurin would be interesting, but it still feels like a squad destined for a playoff exit.

More importantly (at least for Milwaukee), are we confident that this trade would keep the Bucks in a position to contend? As much as the Bucks would love a knockdown veteran like Buddy, he is known for being a stiff non-factor on the defensive end. If the Bucks hypothetically faced Miami in another elimination game next year, would this lineup make you more or less confident? Personally, I’d be more comfortable running it back with Khris.

Middleton opts out, leaves in free agency

This would be a bonafide nightmare for the Bucks. Regardless of Middleton’s future in Milwaukee, the team cannot afford to watch him walk away for nothing. He’s far too valuable.

There’s no reason to panic, though. This feels like the least likely option of the three, given Middleton’s relationship with the team and his high salary for the 2023–24 season. However, this is a business at the end of the day, and if the Bucks are not willing to give him a favorable extension, he could look elsewhere.