After a stunning collapse in the first round of the NBA Playoffs to the Miami Heat, the Milwaukee Bucks have a lot of decisions to make this summer. The team with the best record in the league shockingly failed to live up to expectations, and change is imminent.
One of the most important choices the Bucks will have to make this offseason will be centered around Khris Middleton and the handling of his contract situation. Middleton will be entering the final season of the five-year contract he signed with Milwaukee in 2019 if he opts into his deal.
It is important to note that he has a player option for the upcoming season in 2023-24. If he were to decline his player option, he would become an unrestricted free agent and would be free to sign with any team in the association. With that being the case, there are a few teams that could sign Middleton away from the Bucks this summer.
These 3 teams could steal Khris Middleton from the Milwaukee Bucks
1. Houston Rockets
It is important to remember that any team looking to sign Khris Middleton this summer will need to have ample cap space free to do so. He will be earning a base salary north of $40 million next season, so any team taking him on will have to be certain they believe he is worth the price tag, even on an expiring contract.
With that said, one team that absolutely fits the bill would be the Houston Rockets. They will have the most cap space in the NBA this summer, with a projected $55 to $60 million on the table. On the surface, it may seem ridiculous for Middleton to take his talents from a championship-level team in Milwaukee to the bottom dwellers in Houston. But don’t be so sure.
With the Rockets reportedly being open to moving Jalen Green in favor of adding a star player, Middleton could be exactly what they are looking for. Add in rumors of James Harden having interest in potentially returning to Houston, and the stars could be aligning for the Rockets to make a run at signing Middleton in the near future.

2. Oklahoma City Thunder
Another team that could have a lot of cap room this summer is the Oklahoma City Thunder. Provided they end up waiving all their non-guaranteed players, the Thunder should be able to create enough room to bring on Middleton and his $40 million salary.
OKC is a team that has gained a reputation for taking on bad contracts in order to get back draft picks. If they were to gain Middleton’s services, it would presumably not be through trade, so no picks would be involved here. But what they would get is a high-level scorer that could help them reach the level of playoff contender in the Western Conference.
Middleton would fit in quite well with the Thunder while having Shai Gilgeous-Alexander feed him the ball. His steady shooting would be huge in providing help for SGA offensively, and he could be an effective mentor to up-and-coming players like Jalen Williams.
Having already reached the play-in tournament after being projected to win less than 25 games in 2022-23, the Thunder certainly surprised some teams this year and has to feel they are a piece or two away from becoming a real threat out West. One of those pieces could be last year’s second-overall pick, Chet Holmgren. Throwing in Khris Middleton to the Thunder’s lineup would make them a force to be reckoned with.

3. Portland Trail Blazers
Like the Milwaukee Bucks, the Blazers are another team with a major sense of urgency surrounding their offseason. With time potentially ticking down on Damian Lillard’s time in Portland, the front office is being forced to make moves to revamp their roster. If they don’t, they could end up losing their franchise point guard.
Rather than draft well and hope for the best, the franchise is going to be doing everything it can to bring in veteran win-now players that fit well around Lillard. How they decide to handle Jerami Grant’s situation will dictate how much room they will have for another big contract, but there is little doubt Khris Middleton would fit well in Chauncey Billups’ system.
With Portland lacking consistent shot-makers outside of Lillard last season, Middleton would be a huge boost for a team that is desperate to get back to the status of a playoff contender. The Blazers are also badly in need of more perimeter defense, something that Middleton would be able to bring to the floor from day one as well.
In the event that Khris Middleton declines to pick up his player option, there is always the option that he could re-negotiate his contract with the team and remain in Milwaukee, but the Bucks should definitely be keeping their eyes on these teams as potential party-crashers.
Stay tuned for more Milwaukee Bucks analysis.

