NBA Free Agency 2023: 3 landing spots for Khris Middleton you never thought of

Mar 16, 2023; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Khris Middleton (22) looks to pass against Indiana Pacers guard T.J. McConnell (9) in the second quarter at Fiserv Forum. Mandatory Credit: Benny Sieu-USA TODAY Sports
Mar 16, 2023; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Khris Middleton (22) looks to pass against Indiana Pacers guard T.J. McConnell (9) in the second quarter at Fiserv Forum. Mandatory Credit: Benny Sieu-USA TODAY Sports /
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Feb 6, 2023; Portland, Oregon, USA; Milwaukee Bucks forward Khris Middleton (22) shoots the ball over Portland Trail Blazers forward Jerami Grant (9) in the first half at Moda Center. Mandatory Credit: Jaime Valdez-USA TODAY Sports
Feb 6, 2023; Portland, Oregon, USA; Milwaukee Bucks forward Khris Middleton (22) shoots the ball over Portland Trail Blazers forward Jerami Grant (9) in the first half at Moda Center. Mandatory Credit: Jaime Valdez-USA TODAY Sports /

Khris Middleton could have one of the most unpredictable markets in free agency. These three destinations haven’t been mentioned in rumors but could work.

Khris Middleton will be one of the most interesting free agents to monitor this summer. The three-time All-Star is the ideal modern NBA wing. He is an elite 3-point shooter, who can average 20+ points per game without being ball-dominant. He is also an above-average defender with championship experience. In summary, Middleton is the exact type of player any team could use.

So, every team should be fighting to give him a max contract, right? Well, it is not that simple. Middleton has struggled with injuries over the last couple of years. Last season, it clearly affected his game. He averaged 15.1 points per game and shot only 31.5 percent from 3 (his lowest mark since his rookie season).

In the postseason, he bounced back. In five games, he averaged 23.8 points per game, while shooting 40.6 percent from deep.

Nevertheless, signing the 31-year-old to a long-term deal still carries some risk. Middleton opting out of his $40.4 million player option, signals that he is likely seeking long-term security.

Are the Milwaukee Bucks willing to lock themselves into their current core for the next four years? Can Middleton find a max contract somewhere else? There are a lot of possibilities here.

Let’s take a look at three under-the-radar landing spots for Middleton.

Wild-card landing spots for Khris Middleton: 3. Portland Trail Blazers

The Blazers have been linked to almost every available star over the past month. It is no secret that they would like to pair another star with Damian Lillard. Middleton may not be in the same tier as Paul George or Jaylen Brown, but he would allow the team to preserve some of their young talent. In a potential sign-and-trade, the Blazers would not have to include Scoot Henderson or Shaedon Sharpe.

Middleton would also be a seamless fit alongside Lillard. Lineups with Lillard, Sharpe, Middleton, Grant, and a capable shooting center would give the Blazers shooting and size across the floor.

Here is a potential deal:

Financially, Simons and Nurkic have to be included for the deal to work. Combined, their salaries are worth $40.9 million next season, so the Blazers could offer Middleton about $40 million annually.

Still, is this the best move? Simons is only 24 years old and put up better numbers than Middleton last season. He averaged a career-high 21.1 points along with 4.1 assists. One could argue that Simons is a future All-Star on a manageable contract.

Conversely, is this enough for the Bucks? It depends on how much they value Simons. Nurkic is a solid center, but his three-year, $54.375 million contract hampers his trade value.

Regardless, if the Blazers are truly in win-now mode, this is the perfect trade to appease Lillard.