How the Milwaukee Bucks are set up to contend under new CBA restrictions

LAS VEGAS – When the 2023-24 Milwaukee Bucks take court for the first time this season, much will look familiar. Champions Giannis Antetokounmpo, Khris Middleton, Jrue Holiday, Brook Lopez, Pat Connaughton and Bobby Portis anchor a team that will once again have title aspirations .

Grayson Allen, Jae Crowder and Robin Lopez are veterans who have experience with most of that championship core.

Continuity remains a theme, and it has paid dividends for the Bucks for the last five seasons to the tune of a 69.3% winning percentage in the regular season and a 60% clip in the postseason.

But following the team's free agent signings this summer, including Middleton and Brook Lopez, there is a bit of continuity off the court that is interesting.

First, Crowder, Robin Lopez and Malik Beasley are all on one-year, or expiring, contracts. Allen's contract is also in its final season.

Giannis, several other Bucks players, can become unrestricted free agents following 2024-25 season

But most notably, the deals for Connaughton, Portis, Middleton and Brook Lopez all align with Antetokounmpo’s. They all can become unrestricted free agents after the 2024-25 season, and all but Lopez have player options for 2025-26.

“There is, without a doubt, an intentionality to try make sure that we maximize where we’re at right now with this team and always having an eye toward the future to try to figure out what the next version of this team looks like,” Bucks general manager Jon Horst told The Journal Sentinel.  “That doesn’t necessarily mean that there’s major changes to the roster or there is or there isn’t, it just means that we gotta have an eye toward that and continue to look at how we’re going to build this two, three, four, five years down the road because the whole goal has always been to sustain our success over a long period of time.”

But with a league ecosystem hyper-focused on player movement, attention has already turned to the Bucks and the future of their two-time MVP.

Giannis able to sign maximum extension with Bucks before season begins

Antetokounmpo is eligible to sign another maximum extension before the season begins, though signing it would be somewhat precedent setting – no player his age and with two full seasons of team control left has done such a thing.

Since the creation of the “supermax” extension in 2017, only one player has signed an extension two years before his original max deal expired: Damian Lillard. Lillard did so in 2022, but his situation was much different than Antetokounmpo’s as the Portland point guard was about to turn 32 and had just missed 53 games with an abdominal injury that required surgery.

(Stephen Curry, the first person to sign a supermax, signed his current max extension in Golden State in 2021 when he was 33 years old, one year before becoming a free agent.)

“I know from a media standpoint it’s ‘hey, he’s extension eligible in September’ but at the end of the day he still has three years left on his contract with the player option year at the end,” said ESPN front office and salary cap expert Bobby Marks. “If Giannis had two years left and he was about to become a free agent and he didn’t sign an extension, then I’d be like well, I would be a little more concerned there. It doesn’t really concern me as much because he’s got length on this contract. I think we just talk about it because now there’s a window for him to go out there and do that.”

Bucks looking to the future

Of course, the Bucks would love for Antetokounmpo to sign an extension before the season. But even if he waits, the parallel contracts and infusion of draft picks MarJon Beauchamp, Andre Jackson Jr. and Chris Livingston have set the Bucks up to reboot their roster around Antetokounmpo and any potential max extension that he agrees to years down the line.

This is despite the fact the Bucks are in the second tax apron for this season. Under the new CBA, a team can face harsh roster-building restrictions if it exceeds that second apron multiple times over a four-year period -- something that they now may be able to avoid and still keep their title window open.

“It lines them up to have some flexibility for the post-Khris/Brook years but with Giannis and possibly Jrue still on the team, without getting into that deadly second apron for too many years in a row,” said a league salary cap expert unaffiliated with the Bucks.

Marks agreed.

“I think that’s a big reason why Brook’s contract is two years and Khris’ number is lower and we’ll see what happens with Jrue here,” Marks said. “I think it’s a big reason why they went out and got the two draft picks in the second round because you have to have back-end guys.

"You have to have this young infrastructure of players and if you don’t have the draft pick capital it’s hard because you’re spinning the minimum wheel every year, you’re cycling through six or seven guys every year and that is extremely hard to do. That’s why you need MarJon and then Andre and then Chris eventually to play a role. Those guys will need to play a role just because of where these rules are going to be.”

This article originally appeared on Milwaukee Journal Sentinel: How the Bucks are set up to contend under new CBA restrictions