How the Bucks’ negotiations with Giannis Antetokounmpo’s aging teammates could clear the Cavs’ path to contention

Cavs, Bucks

Giannis Antetokounmpo will never let the Bucks be bad. But can Milwaukee toe the line between building around him now and planning for the future? AP

CLEVELAND, Ohio -- Giannis Antetokounmpo wanted to defend Jimmy Butler, and after the Greek Freak missed his chance, his coach got fired.

That’s not to say Antetokounmpo requested the change. He doesn’t solicit such drama like some other NBA superstars. But the Bucks still cater every move to his needs because he is that good. Milwaukee won at least 63% of their games in all five seasons under Mike Budenholzer, and its front office knew which employee (hint: not the coach) played a larger role in that success.

So when a reporter asked Antetokounmpo whether Milwaukee adjusted well enough to defending Butler, who averaged 37.6 points per game during a 4-1 series win over the Bucks, you can bet Milwaukee’s front office listened close to his answer.

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“No, we didn’t,” Antetokounmpo said. “I think Jrue (Holiday) did his best man, but at the end of the day, he gets tired. He’s got to rebound the ball, he’s got to pass the ball, he’s got to score the ball, he’s got to guard Jimmy. You get tired. Maybe we could’ve done some double teaming more, make him pass the ball, maybe switch the matchup for a while, give Jrue a break. But I don’t think we as a team made the right or as many adjustments as we could against him.”

Would he have liked to defend Butler more himself?

“Yes,” Antetokounmpo said.

The Bucks fired Budenholzer one week later, not solely because Antetokounmpo critiqued him in a press conference, but not without the superstar’s approval. In Milwaukee, the right move is what keeps Antetokounmpo satisfied, which is why the decisions they face this summer are so complicated.

To stay in title contention, the Bucks must keep forward Khris Middleton (player option) and center Brook Lopez (unrestricted free agent). But signing either player to a contract too expensive or long could hinder Milwaukee’s long-term plans. And with two years until Antetokounmpo must decide on his own player option, the Bucks can’t afford to hinder either timeline.

That makes their offseason another for the Cavs to monitor this summer. Cleveland can’t match the Bucks’ standard (five straight one seeds) now, but Milwaukee’s looming decisions could loosen its foothold in the East.

The Aging Co-star Conundrum

Brook Lopez finished second in Defensive Player of the Year voting and accumulated the second-most win shares (eight) of his career last season. He will also turn 35 next season, and basketball reference counts just 40 seasons (by 20 players) where a 35-year-old has contributed to winning at Lopez’s 2022-23 clip.

Ten of those 20 players are big men, who generally age better than guards, but Milwaukee can’t know when Lopez might meet his drop off, which makes it hard to calculate the right salary (and length) on a contract. The Bucks will face competition for Lopez, too. Teams like the Rockets, who project to have $47 million in cap space this summer, need the defense and shooting Lopez provides, and they can pay a prettier premium than Milwaukee.

Speaking of premiums, Middleton can opt into a $40-million player option if he would rather wait a year to re-negotiate his value. But he also might prefer long-term security over risky cash grab, and that’s where his contract talks could turn tricky.

Middleton was, at his peak, the closer for a Bucks team that won the 2020-21 NBA title. But since then, he’s missed 74 of a possible 181 games with wrist and knee injuries that both required surgeries. And even when he was healthy last season, he posted the worst field goal percentage of his career (43.1%).

He bounced back in the playoffs, during which he averaged 23.8 points, 6.4 rebounds and 6.2 assists on 46.5% shooting against the Heat (five games). But he had his knee surgery after that series, and he turns 32 this summer.

The question concerning both Middleton and Lopez: Can Milwaukee offer a contract that satisfies its free agents’ long-term interests while protecting its own?

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Retain or Re-tool

The short answer above is they have to. Unless the Bucks cut or trade every player they employ besides Antetokounmpo and Holiday, they can’t create the flexibility to add costly replacements for Lopez and Middleton If they did strip the roster, they’d be picking from a fickle free agent market -- top options include James Harden, Kyrie Irving and Draymond Green -- or trading picks and players (including Holiday?) for a disgruntled star, leaving little room to sign role players.

Signing Lopez and Middleton locks in a supporting cast around Antetokounmpo that will only decline with age, however, and it could push Milwaukee toward the “super tax” salary cap apron, which harshly penalizes teams for spending $17.5 million over the luxury tax line (The Bucks are $16 million below that apron when accounting for Lopez’s $20-million cap hold and Middleton’s $40-million player option).

If teams exceed the apron, they can’t use their mid-level exception, which is a valuable tool for expensive, contending teams hunting for role-playing free agents. They can’t trade their first-round pick seven years ahead, which could hurt their ability to bundle picks for stars. And they can’t sign buyout players (among other penalties), who often sign cheaper contracts with contenders after their original team waives them.

These sacrifices are worth it if your team is winning big. But given the uncertainty surrounding Middleton and Lopez’s future performance, Milwaukee will likely factor the apron into their negotiations with each player.

Cavs’ perspective

No matter which direction Milwaukee chooses, the Cavs can seize an opportunity.

If the Bucks lose Lopez and/or Middleton, the East’s top seed grows weaker. Neither player can be replicated by a low-cost option, and we saw this postseason how messy the conference’s power struggle can be when the Bucks are weakened.

If the Bucks keep both players, they would muddy Cleveland’s immediate path to contention as well as their own future. In three years, the Cavs might be the best version of themselves. Meanwhile, Lopez and Middleton will be 37 and 34, respectively. Will they still be good enough to support Antetokounmpo then?

Milwaukee will never be a bad team as long as it employs its star, which is why it works so hard to keep him happy. But co-stars like Lopez and Middleton are the difference between good and best in the East, a title that the Bucks have held (by record) for half a decade. Milwaukee can’t afford to lose them now or keep them for too long, which puts the East’s pole position in a precarious state.

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