Sep 21, 2023, 08:00 AM ET

Milwaukee Bucks star Giannis Antetokounmpo becomes eligible to sign a contract extension on Friday, his first chance to recommit to the franchise since he signed a supermax extension before the 2020-21 season.

Antetokounmpo still has two years remaining on his contract, plus a player option for a third year, but his timeline toward free agency is ticking quickly. For now, Antetokounmpo, 28, remains committed to the Bucks, but he has reiterated this offseason that his loyalty to the organization is contingent on the team remaining in championship contention.

Every season of Antetokounmpo's career comes with heightened expectations. Already a two-time MVP, he averaged a career-high 31.1 points, 11.8 rebounds and 5.7 assists during the 2022-23 season and finished third in MVP voting.

Yet, the Bucks are coming off a disappointing finish in last year's postseason, going from the No. 1 overall seed in the playoffs to losing in five games to the Miami Heat in the first round, a series in which Antetokounmpo missed two games because of a back injury.

Milwaukee is about to enter one of the most pivotal stretches in franchise history. From the moment Antetokounmpo becomes eligible to sign an extension until the day he signs it or signals his intentions not to, all eyes around the league are going to be monitoring his contract status closely.

Tim Bontemps, Jamal Collier and Bobby Marks teamed up to break down the biggest questions facing Antetokounmpo and the Bucks as they enter this crucial period.

What is his current contractual status?

Antetokounmpo signed a five-year, $228 million supermax extension in December 2020 and is under contract for this season and next, with a player option for the 2025-26 season. If he declines it, he would become an unrestricted free agent for the first time.

2023-24: $45.6M
2024-25: $48.8M
2025-26: $51.9M (Player option)

The $45.6 million salary this season represents 33.55% of the Bucks' salary cap, below the maximum salary for a player that has 10 years of service or more. That is a result of the salary cap remaining flat in 2020-21 and increasing only 3% in 2021-22, the first year of the extension, due to revenue losses during the COVID-19 pandemic. Antetokounmpo will be the seventh-highest paid player in the NBA this season, behind Stephen Curry, Kevin Durant, Nikola Jokic, LeBron James, Joel Embiid and Bradley Beal.

What extension is he eligible to sign?

With two years remaining on his contract before he can be an unrestricted free agent, Antetokounmpo is eligible to sign a three-year extension worth roughly $169 million.

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The extension, however, is worth only $117 million in new money because his $51.9 million player option would be replaced with a salary starting of $52.2 million in 2025-26.

The extension could increase to $186 million if the salary cap increases by 10% in both 2024-25 and 2025-26. The NBA sent a memo to teams in late June, projecting the cap increasing 4.4% in 2024-25.

Because Antetokounmpo is considered to have two years left on his contract (the player option does not count), the deadline for him to sign an extension is Oct. 23, the last day before the start of the regular season.

Is he better off waiting to sign next summer?

In many ways, yes.

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First, he can see where Milwaukee's roster stands, just as he did before signing his current contract, when he waited for the Bucks to trade for Jrue Holiday before committing his future to Milwaukee. How the Bucks finish in 2023-24 will also be a significant factor.

Second, he can guarantee himself significantly more money, as he can sign a four-year extension worth roughly $234 million (could increase to $258 million if the cap increases 10%) next summer, as opposed to a three-year extension this year. He can sign that extension any time from July 6, 2024 through June 30, 2025.

Has he said anything about signing an extension?

For years, Antetokounmpo had expressed an interest in remaining in Milwaukee for his entire career.

"Kobe [Bryant] did it. Tim Duncan did it. Dirk Nowitzki did it. I just want to be one of those guys ... that stays for the city, play for the city for 20 years," Antetokounmpo told ESPN in 2018.

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However, his tune changed dramatically during an interview with the New York Times last month, in which Antetokounmpo made it clear his loyalty would come with conditions.

"Next summer it would make more sense for both parties. Even then, I don't know," Antetokounmpo said about signing an extension. "I would not be the best version of myself if I didn't know that everybody's on the same page, everybody's going for a championship, everybody's going to sacrifice time away from their family like I do. And if I don't feel that, I'm not signing."

He backed that up last week on the "48 Minutes" podcast, saying "I'm a Milwaukee Buck, but most importantly I'm a winner. ... If there is a better situation for me to win the Larry O'Brien [Trophy] I have to take that better situation."

How have the Bucks approached this?

Antetokounmpo's stance has been steadfast for years: He expects to be on a team that is consistently in contention for championships. After last season's stunning first-round exit, the Bucks fired coach Mike Budenholzer and replaced him with former Toronto Raptors assistant Adrian Griffin. Milwaukee also re-signed longtime franchise pillars Khris Middleton and Brook Lopez. Middleton's contract purposely aligns with Antetokounmpo's: two years, plus a player option in 2025-26.

Antetokounmpo's public comments last month will most likely put significant pressure on the franchise to win this season, and the Bucks enter the 2023-24 season with the fourth-best odds to win the title according to Caesars Sportsbook.

"Giannis and I are on the same page," Griffin said during a charity golf outing on Sept. 11. "He wants to win, and I want to win. It's that simple. I respect him. I respect what he's accomplished in this league. We're here together to win. I have no problem with that. I think it's a great partnership. We're going to lead the team together."

What is the state of the rest of the Bucks' roster?

With Middleton and Lopez locked up for the next couple of seasons after signing new deals this summer, the other big question to answer regarding Antetokounmpo's supporting cast is Holiday, who can become an unrestricted free agent next summer. Holiday will also be eligible for a contract extension beginning Feb. 22. A four-year, $223 million extension would start in 2024-25 and would see Holiday earn $61.6 million at the age of 37 in 2027-28. Because of the Over-38 rule, Holiday is not allowed to sign a five-year contract with Milwaukee if he declines his player option and becomes a free agent in 2024.

The Bucks would have only the $12.9 million non-taxpayer midlevel exception to replace Holiday if he leaves in free agency, so if Milwaukee wants to remain a title contender moving forward, it will almost certainly have to keep Holiday in the fold.

How much longer will this team be in championship contention even if Antetokounmpo stays?

It's unclear. The Bucks have won 271 games since the start of the 2018-19 season, the most in the NBA in that span. They've been to two Eastern Conference Finals, won the title in 2021, and had advanced in the playoffs for four consecutive seasons prior to last season's shocking first-round upset.

That said, changes could be on the horizon. There isn't a single player who has a contract for the 2025-26 season on the roster, though several players (Antetokounmpo, Middleton, Bobby Portis and Pat Connaughton) all have options for that season.

Beyond that, it's a group of talent that is aging out of its prime. Lopez is 35. Holiday is 33. Middleton is 32. And there isn't much youth coming up behind them on the roster, an understandable consequence of being a veteran team chasing a championship that has sacrificed draft capital in trades to improve the roster, most notably for Holiday.

Milwaukee has already traded its 2025 and 2027 first-round picks, and the New Orleans Pelicans own swap rights on the picks in 2024 and 2026. The Bucks only have one first-round pick (either 2029 or 2030) available to trade. To make matters worse, Milwaukee has one second-round pick (2024 from Indiana) in the next seven years.

How does the new collective bargaining agreement impact Milwaukee?

The Bucks have a projected $182 million payroll this season and were not allowed to use the $5 million taxpayer midlevel exception because they were considered a second-apron team. The same rule holds true next offseason if the Bucks are once again over the second apron, which they project to be if they retain Holiday.

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The longer the Bucks remain above the second apron, the more restrictive the penalties become, including the inability to send cash in a trade, the inability to aggregate contracts for trade matching purposes, and the potential freezing of future draft picks.

That could make it considerably more difficult to build a championship roster around Antetokounmpo as some of those restrictions take effect in future years, unless the Bucks find a way to lower their overall payroll without sacrificing talent.

What happens if Antetokounmpo won't extend his contract next summer?

To find the closest analog to Milwaukee's situation, consider the situation the Oklahoma City Thunder found themselves in with Kevin Durant from 2014 to 2016.

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There were no financial incentives for Durant to extend with his original team, and so he reached unrestricted free agency and subsequently signed with the Golden State Warriors in 2016. That decision ushered in the idea of the supermax contract extension in the collective bargaining agreement that went into effect in 2017, which was designed to give teams like the Bucks some level of clarity on what a star of Antetokounmpo's magnitude will decide to do before he can leave the team for nothing as a free agent.

No player of Antetokounmpo's stature in the intervening six years has been in this position and not signed an extension. While Milwaukee could bank on Antetokounmpo preferring the financial incentives to sign next summer to convince themselves not to trade him this season, if things go wrong -- for example, if Holiday doesn't extend or re-sign and the team has another disappointing finish -- the Bucks could at least begin exploring trade options for Antetokounmpo with an eye towards retooling the roster for the future.

Which other teams are keeping a close eye on the Antetokounmpo situation?

It's still early, so Milwaukee hasn't crossed the bridge of trading Antetokounmpo just yet, but when a player of his talent level has question marks about his future, teams around the league begin to act accordingly in case he becomes available. A lot could hinge on whether he makes specific requests, like playing in a larger market, as some players have when asking for a trade recently.

A few preliminary teams, who at the very least, will be watching this situation closely, could include the New Orleans Pelicans, Toronto Raptors, Brooklyn Nets, New York Knicks and Golden State Warriors, according to Zach Lowe and Ramona Shelburne during a recent episode of the Lowe Post podcast. Each of those teams have a combination of intriguing young players and valuable draft picks available that could be packaged in the kind of trade it would theoretically take to land Antetokounmpo.

Giannis antetokounmpo milwaukee bucks contract extension questions

2023-09-23 21:00:39