What’s next for Bucks? Milwaukee must balance current title window with long-term ambitions in critical summer

Only one member of the 2020-21 NBA champion Milwaukee Bucks is still alive in the 2022 playoffs, and as you likely knew, he no longer plays for the Milwaukee Bucks. After winning the title, Milwaukee had two key free agents to try to re-sign. Bobby Portis was willing to take a discount to stay with the Bucks. P.J. Tucker was not. So Milwaukee filled Tucker’s salary slot with Portis and returning free agent George Hill, and Tucker received a warm welcome from one of Milwaukee’s biggest rivals: the Miami Heat. Tucker’s Heat will now face the very Boston Celtics team that knocked Milwaukee out of the playoffs for a chance to return to the NBA Finals.

Should the Bucks have retained Tucker? Yeah, probably. There was no apparent basketball or collective bargaining issue preventing a reunion. Milwaukee could have kept him through Bird Rights. The only cost would have been financial. The small-market Bucks are already paying a hefty luxury tax bill. Adding Tucker’s $7 million salary to their present cap sheet would have cost almost $40 million once taxes were factored in. That was untenable to ownership, so in a Game 7 in which they shot 4-of-33 from behind the arc and could play Portis just 22 minutes due to his defensive deficiencies, they had no Tucker alternative to turn to. If Tucker was still a Buck, Milwaukee’s entire roster might be joining him in the Eastern Conference Finals.

But losses like Tucker’s are relatively common among contenders. Champions crumble through compromise. Rosters get older. They get more expensive. Role players want to be treated like starters. Starters want to be stars. The realities of the basketball business chip away at the NBA’s best teams until entropy turns them into mere shells of their former selves. 

We’re not quite there with the Bucks yet. Tucker or no Tucker, Milwaukee probably wins this series and maybe even the championship if Khris Middleton is healthy. But the compromises are already starting to accumulate. Milwaukee traded for Grayson Allen in part as a hedge against losing Donte DiVincenzo. Allen was willing to sign the sort of extension they were comfortable paying a low-end starting shooting guard. DiVincenzo wasn’t. DiVincenzo, when healthy (which he never was for Milwaukee this year) is a sturdy defender and capable ball-handler. Allen was neither of those things in this series. Milwaukee lost this series by 55 points. They lost Allen’s minutes by 48.

The shooting guard that actually led Milwaukee to the title is also eligible for free agency this offseason. After strong showings in back-to-back postseasons, Pat Connaughton appears likely to decline his player option and hit the open market. Milwaukee could re-sign him. Doing so might cost the Bucks Portis, who also has a player option. Milwaukee has four players making a combined $126 million next season and is already flirting with the tax line before new deals for Portis and Connaughton are even factored in. They’re going to draw a line somewhere.

This entropy robs winners of the players they’ve won with, but it’s even crueler to those that remain. The Bucks are getting old. Aside from Giannis Antetokounmpo, they have team control over just three players in their 20s next season: Allen, Luca Vildoza and Rayjon Tucker. The trio of Middleton, Jrue Holiday and Brook Lopez was good enough to buttress Antetokounmpo’s title chase last season. They likely would have been this season, and if the band stays together next year, Milwaukee is going to be among the favorites.

But Lopez is 34, on an expiring contract and had to overcome back surgery to play for Milwaukee this postseason. Holiday has missed 10 or more games in six of his past eight seasons. Middleton is eligible for an extension this offseason that would tack an additional $152.5 million onto the $78 million he is already owed.

The Bucks would be more than justified in paying that. Just ask Phoenix how fleeting championship windows can be. Milwaukee’s is open for the time being. A couple of bad years on the backend are a price worth paying for an extended window. The Bucks already have one title. They might get a second or third with this group.

But lingering here is the reality that Antetokounmpo is probably going to outlast every other existing Buck. Milwaukee has three years of team control over the best player in the world at the age of 27, and when that time is up, he’s said himself that it’s no longer a given that he stays put. “Me and my family chose to stay in this city that we all love and has taken care of us—for now,” Giannis said in an interview with GQ in November. “In two years, that might change.” 

In two years, Antetokounmpo will be 29 on an expiring contract playing for a team paying max money to two potential future Hall of Famers likely on the decline. This isn’t to drum up the sort of free agency hysteria that preceded his last contract extension, but rather, an acknowledgment of the simple fact that a two-time MVP is probably going to keep wanting to win into his 30’s, and if the Bucks keep letting entropic agents like Father Time and the almighty dollar gradually weaken their supporting cast, they’re going to have a hard time convincing Antetokounmpo that they can give him the roster he deserves for as long he deserves it.

That’s the needle Milwaukee is going to have to try to thread at some point. They have to find a way to extend their current window without closing it, to get younger and cheaper without getting much worse. Doing so is going to require some appetite for risk.

Exploring Lopez trades might be worthwhile. Even at his advanced age, he’s an exceedingly rare big man. The list of elite rim-protectors that can also space the floor is short. Those that can do so with the capability of scaling up as an interior scorer and surviving as a perimeter defender are rarer, and at the reasonable price of $14 million for next season, the Bucks could likely score multiple assets for a player without whom they survived for most of the regular season. The ideal solution here, even removing the higher-end outcomes, is something like the trade San Antonio made for Kawhi Leonard once upon a time: a deal in which the Spurs recognized their need for youth and turned an established veteran (Hill) into a mid-first-round pick they could use on someone they viewed as a long-term fit.

The bigger dice roll would be sniffing around Middleton’s market before he gets locked into a long-term extension. Milwaukee just came one game away from beating Boston without him, and he’d likely fetch a package that could reshape the Bucks for years. Is Portland desperate enough to give Damian Lillard a winner that it would dangle Anfernee Simons and its lottery pick? The Kings are probably desperate enough to make the playoffs to give up Harrison Barnes and their own pick, depending on where it lands. Such a deal would rely on Milwaukee falling in love with someone else’s young player or a draft prospect. It would also represent perhaps the biggest gamble a general manager has made since Sam Presti traded James Harden. The Bucks know, for a fact, that the trio of Antetokounmpo, Middleton and Holiday can win a championship. Teams simply don’t break such groups up without feeling extremely confident in what’s behind Door No. 2. Without a top-five pick or proven youngster coming back to Milwaukee, the risk here outweighs the reward.

But some risk is going to be necessary, because Milwaukee’s supporting cast is probably going to continue to degrade without a significant infusion of young talent. The Bucks will have a few traditional opportunities to find it this offseason. They’ll have the No. 24 pick in June’s NBA Draft before forking over three of its next five selections thanks to the Jrue Holiday trade. Winners typically use their mid-level exceptions on proven veterans. The Bucks could use it to take a swing on a younger free agent. The Bucks gave 23-year-old Jordan Nwora every opportunity to earn a rotation spot early in the season. If he’s re-signed, they could give him another chance next year.

This is a first-world problem. Most teams would kill for any chance to win at the level Milwaukee has over the past several years. Having Antetokounmpo means having the luxury to think in grander terms than most of the league. This iteration of the Bucks is built to win right now. The goal of this offseason will be figuring out how to position the next iteration of the Bucks for similar ambitions, because if they don’t take some step in that direction now, they’re going to start seeing more and more of their players suiting up for other contenders without having any way of replacing them.