Khris Middleton, Bucks Agree to New 3-Year, $102M Contract in Free Agency

The Milwaukee Bucks won't be shaking things up after agreeing to a three-year, $102 million contract with Khris Middleton, according to ESPN's Adrian Wojnarowski.

Middleton declined his $40.4 million player option in June. The move wasn't surprising since he was poised to secure a massive long-term deal wherever he signed. It didn't rule out a return to Milwaukee, either.

Yahoo Sports' Jake Fischer reported on June 15 the Bucks "by all accounts" were looking to retain Middleton and unrestricted free agent Brook Lopez. HoopsHype's Michael Scotto reported on June 18 that was the expectation around the league and that the 6'7" forward could potentially earn $130 million over four years.

Middleton's value didn't take much of a hit despite his disappointing 2022-23 season. He missed the start of the year while recovering from wrist surgery and battled knee trouble before having surgery to address that issue after the Bucks were bounced from the playoffs.

In 33 regular-season games, the three-time All-Star averaged 15.1 points and 4.9 rebounds while shooting 31.5 percent from beyond the arc. His performance improved in the playoffs as he put up 23.8 points per game and connected on 40.6 percent of his threes in the first round.

To the extent there was any uncertainty over Middleton's future, it stemmed largely from how this offseason is Milwaukee's chance to make any sort of consequential pivot while Giannis Antetokounmpo is under his current contract.

The organization already fired head coach Mike Budenholzer and replaced him with Adrian Griffin in the wake of a bitterly disappointing postseason. Maybe the front office was starting to have reservations about Middleton and Jrue Holiday's suitability as the co-stars alongside Antetokounmpo as well.

The other factor to consider is how keeping this core together will be very expensive at a time when the collective bargaining will further hamstring the teams deepest into the luxury tax.

Middleton and Lopez reached the open market this summer, with Holiday eligible to opt out in another year.

Retaining all three means the Bucks will be boxed in roster-wise for the foreseeable future, and The Athletic's Eric Nehm explained how the effects of the CBA might already show themselves:

"That is why every single dollar is going to matter this offseason and why the negotiation on every deal the Bucks make will be critically important to Horst. If the Bucks end up bringing back Lopez and Middleton, Horst may need to consider trading one of their mid-level earners — Portis ($11.71 million), Connaughton ($9.42 million), Allen ($8.93 million) — before free agency begins to cut down the team's salary and keep the Bucks under the second salary-cap apron."

When Middleton, Lopez and Holiday are all north of 30 years old, perhaps getting a bit younger could ultimately widen a championship window.

In reality, general manager Jon Horst may not have had much of a choice.

By letting any one of Middleton, Lopez or Holiday walk, the Bucks risk going backward, and even a temporary setback could have significant ramifications for Antetokounmpo's future. He'll presumably opt of his final year in 2025.

There's nothing to indicate the two-time MVP is a serious flight risk, and his nuanced comments after the season ended illustrated how he doesn't view success in binary terms.

Still, Milwaukee can't take Antetokounmpo's loyalty for granted. And while he may not operate with a championship-or-bust mindset, he'll want to be on a team that can consistently put him on solid footing to chase a second title.

Keeping Middleton on the roster was the most sensible decision for Horst because there was almost no path to replacing him with a star of similar value. The only hope is that the 31-year-old can avoid the injury problems that have limited him the last two seasons.