The Bucks Are In a Tough Spot
On the Milwaukee Bucks outlook and why they have a complicated path forward even if they get a generational haul for Giannis Antetokounmpo.
The Milwaukee Bucks have done everything in their power to maximize the present around Giannis Antetokounmpo. Since his ascension to MVP status in 2019, they’ve made several aggressive moves to build a roster capable of contending for a championship. These moves have resulted in seven playoff berths, two Eastern Conference Finals appearances, and an NBA championship.
These moves came at the cost of mortgaging future draft picks as far out as they can. They were risky since one bad year could mean losing a valuable selection. But as long as Antetokounmpo was a Buck, they’d at least be competitive. This is what they were banking on and still are to this day.
Now the Bucks are facing one of the worst-case scenarios with Antetokounmpo starting to lose faith in them. Last week, Shams Charania reported that Antetokounmpo and his agent will begin conversations with the Bucks about whether his fit is best with the Bucks or elsewhere.
This is the second time this year Charania reported on Antetokounmpo’s open-mindedness playing elsewhere. This initial soft-launch trade request was followed up in October with a report that the Knicks are his top and only destination. No trade materialized, so when he had a chance to address the reports in training camp, he didn’t deny them but expressed his commitment to the Bucks for this season.
It appears that non-binding commitment is already wearing thin. The Bucks got off to a strong start to the season with Antetokounmpo carrying the load with MVP-level numbers. They are now 10-15 and losers of 10 of their last 12 games. In that stretch, they lost all six games he missed and are .500 when he’s active.
The Bucks weren’t expected to be contenders this year, but they’re performing worse than what their expectations probably are. Their current standing puts them on the cusp of not securing a top-10 seed for the Play-In Tournament. Things probably won’t get better anytime soon, with Antetokounmpo expected to miss 2-4 weeks with a calf strain.
So far, the Bucks have reportedly not fielded trade inquiries on Antetokounmpo, according to Jake Fischer. They’re right to posture for now, but the noise of the past seven months paints a compelling picture. It feels like he has requested a trade, even if he refuses to explicitly make one. But their path forward is muddled even if they land a megahaul due to their outgoing pick obligations.
The Bucks experienced their first taste of being a true contender in 2019. Antetokounmpo’s supporting cast included co-All-Star Khris Middleton and Brook Lopez, who the league ignored in 2018 free agency. The Bucks were able to sign him for virtually the minimum. They couldn’t re-sign both players in 2019, so they creatively used cap space in 2019 to re-sign both players to contracts higher than their Bird rights allowed.
In 2020, the Bucks were the top seed in the East for a second straight season. They were expected to build off their 2019 Conference Finals run with a trip to the Finals. Instead, they were surprisingly disposed of by the Heat in five games. The series was never close, and it put both head coach Mike Budenholzer’s job certainty and the roster into question.
They needed to make a move. So in the 2020 offseason, they made one of their first aggressive win-now trades in the decade by acquiring Jrue Holiday from the Pelicans. They had few expendable players with positive value to offer, but they included Eric Bledsoe and George Hill primarily as matching salary. The value sent out was unprotected first-round picks in 2025 and 2027 and first-round pick swaps in 2024 and 2026.
The price paid off immediately when the Bucks won the 2021 championship. It was a strange season post-COVID lockdown with many high-profile players getting injured during the playoffs, but it was a championship nonetheless. History will remember the victors over the details of who was or wasn’t available in their path.
The Pelicans knew that any Bucks first-round pick wouldn’t be valuable as long as they had Antetokounmpo, so they wisely negotiated for draft picks as far out as possible. So far, these selections have resulted in the 19th overall pick (2025) and a two-selection rise from the swap (2024). Now the remaining owed selections, particularly the 2027 first-round pick owed to the Pelicans or Hawks, could be of high value with the Bucks projected to finish in the lottery for the first time since 2016.
The Bucks would remain a top seed in the East for the next two years but failed to reach the heights of their 2021 title. The franchise reached a crossroads in 2023 when they were ousted by the Heat again in five games, this time as a one-seed favored by many to reach the Finals. The moves that followed would, in retrospect, mark the beginning of the end of the Antetokounmpo era.
They reacted to the early playoff exit first by firing Budenholzer. They replaced him with Adrian Griffin, who, along with David Blatt, shares one of the shortest tenures coaching a contender in recent history. Doc Rivers has since been in charge, but the constant turnover at the coach position felt like the first sign of some organizational instability.
They also got the chance to acquire Damian Lillard out of the blue and took it. He requested a trade from the Blazers, and it was known publicly that he only wanted to play for the Heat. However, he had little leverage to control his destination since he had just signed a two-year extension the year before that put him under contract through 2027. That benefited a darkhorse suitor like the Bucks.
In exchange, the Bucks sent Jrue Holiday and Grayson Allen to make the salaries work. They also traded whatever draft capital they had left at the time: an unprotected 2029 first-round pick and swaps in 2028 and 2030. They had yet to convey a single draft pick in their Holiday acquisition, and they just went ahead and traded whatever they had left for Lillard.
The move backfired as the fit between Antetokounmpo and Lillard wasn’t as complementary as many projected. But it’s hard to knock the Bucks for making the move. It was a low price to pay for a perennial All-NBA player compared to the cost that inferior players went for recently. You’d be hard-pressed to find a large coalition of NBA personnel who wouldn’t have done this if they were the Bucks.
The trade also led Antetokounmpo to sign a maximum extension. He only had two years left on his deal before he could opt out and become a free agent in 2025. The extension added two more guaranteed years and keeps him under contract until at least 2027. That alone made the Lillard acquisition worth it.
The Bucks would continue to flame out in the first round of the playoffs with Lillard. Both he and Antetokounmpo were limited by injuries in both the 2024 and 2025 playoffs, but it’s hard to envision them making a meaningful run if they advanced.
Even with Antetokounmpo still around, an era of Bucks’ basketball is over with mainstays Holiday, Middleton, and Lopez gone. After three straight first-round exits and the reality that Lillard would miss the 2025-26 season with a torn Achilles, their franchise player is now thinking about his options elsewhere.
The Antetokounmpo extension was a major lifesaver for the Bucks. Not only to remain competitive, but also for a potential trade. The idea is that he’d sustain his trade value by adding more years onto his contract. In a vacuum, a top-3 player in the league is worth multiple draft picks, starting-level veterans, and promising prospects. He should be the type of player who nets a haul reminiscent of what the Nets got for Kevin Durant.
However, the current market may not have the appetite for that. As great as Antetokounmpo is, he’s a player whose game relies on athleticism who just turned 31 years old. He’s also a little more injury prone, having missed at least 15 games per season in four of the past five seasons, including the current one.
According to Brian Windhorst, teams are reluctant to part with multiple first-round picks in one trade. These types of trades were most frequent between 2019-2023, with the Durant deal being the peak of that era. This was never going to happen, but this may have been the time to truly capitalize on Antetokounmpo in a trade.
These trades still happen occasionally, such as the Knicks trading five first-round picks for Mikal Bridges in 2024. The Magic also just traded four first-round picks for Desmond Bane in June. It just takes one team to be convinced they’re a Giannis away from a championship and emptying the cupboard for him. But the demand leaguewide needs to be there for him. It seems inexplicable that Antetokounmpo might not net much more than these players who never even made an All-Star team.
We’ve dissected the Antetokounmpo trade landscape thoroughly on Third Apron. We highly recommend you listen to our two-part series on his trade market, where he discussed his best fits and what offers could look like from these teams. These all assume a trade is consummated ahead of the February 5 trade deadline.
But the Bucks’ overall direction is complicated even if they get a generational haul. It wouldn’t solve the issue that they owe many draft picks to many different teams. Unlike the Nets in their 2024 trade with the Rockets, there is no single trade they could make to regain control of their draft picks.
To recap, they don’t have control of the following picks to the following teams:
2026 first-round pick swap: Pelicans or Hawks
2027 first-round pick: Pelicans or Hawks
2028 first-round pick swap: Blazers or Wizards
2029 first-round pick: Blazers or Wizards
2030 first-round pick swap: Blazers
The one silver lining of all this is that the Bucks could comfortably bottom out for a high draft pick in the 2026 Draft. They don’t need to worry about swapping out a valuable pick because the Pelicans, who currently have the worst record in the league, are so bad. The swap prevents them from getting the first-overall pick, but they’d have a high lottery selection.
After that, the Bucks have no incentive to lose and even fewer incentives to offer these teams to regain control of their picks. What’s also further complicating some of these outgoing selections is that they are encumbered with multiple teams.
For example, the Pelicans traded the least favorable of their own and the Bucks’ 2027 first-round pick to the Hawks as part of the Dejounte Murray deal. Because of this, the Bucks would need to make trades with both the Pelicans and Hawks to regain full control of just their 2027 first-round pick.
The Bucks also traded their 2028 first-round pick swap twice, once to the Blazers in 2023, then again to the Wizards in 2025 as part of the Kyle Kuzma trade. The Wizards also have a stake in the Bucks’ 2029 first-round pick since the Blazers traded them the second-most favorable of the Bucks, Celtics, and their own 2029 first-round pick as part of the Deni Avdija trade. The Bucks would need to make trades with the Blazers and Wizards to regain full control of their 2028 and 2029 picks.
Could this predicament motivate the Bucks to seek a return that maximizes the present? For example, if the Knicks are willing to trade both Karl-Anthony Towns and OG Anunoby for Antetokounmpo, Kuzma, and Bobby Portis, that might be the best offer the Bucks get for remaining competitive now. The Pacers could also make a similar offer centered around Pascal Siakam and other players, if Antetokounmpo is interested in joining them.
The Bucks will naturally want draft picks and talented young players, but maybe they’d compromise on that to remain competitive. It feels like the most likely return is a balance of the two and veterans who can help them now.
They could then reroute pieces of their return to hopefully regain control of their picks or pursue other targets. For example, the Blazers’ return for Lillard and Holiday was underwhelming outside of Toumani Camara, but they were able to salvage it by rerouting a 2029 first-round pick for Avdija. They could acquire an All-Star-level player for Antetokounmpo now, try to compete, then potentially trade him later for draft picks, if he sustains his trade value.
Another issue the Bucks could face in the future is limiting cap flexibility. Lillard tearing his Achilles effectively left them with $54 million in dead money for the 2025-26 season. It likely would’ve cost them their one tradeable first-round pick in either 2032 or 2033 just to get a team interested in taking him on. That seemed like a non-starter with the uncertainty surrounding Antetokounmpo’s future.
Father Stretch My Contract
At the start of free agency, Shams Charania reported that Myles Turner would sign a four-year, $107 million contract with the Milwaukee Bucks. The simplest way to acquire him would be through a sign-and-trade. Otherwise, they needed cap space, meaning they needed to clear $30 million in salary.
Instead, they shocked the NBA world by waiving and stretching the remainder of Lillard’s contract over five years. The move, along with several other trades, resulted in the required cap space to sign Myles Turner. He will naturally also become a trade candidate if Antetokounmpo is traded, but that is TBD.
Either way, it’s not looking like the player the Bucks got in Turner or the potential return they could get for him in a trade will be worth the $22.5 million in dead money over the next five seasons. This could hamper their roster construction if they remain competitive. They’ve spent nearly $220 million in luxury tax penalties this decade and are actively trying to duck the tax. Tax avoidance with 15 percent of a team’s cap tied up in dead money isn’t a winning combination.
This could complicate the Bucks’ efforts in a potential rebuild as well. They could become a team with significant cap space or create large trade exceptions by trading Antetokounmpo and Turner. They could use this cap flexibility to take on bad contracts with draft picks attached, or throw a significant offer sheet at a top restricted free agent. Lillard’s dead money could limit the extent to which they use this hypothetical flexibility.
It’s going to be challenging for the Bucks to gauge the market for Antetokounmpo, field offers, and trade him within two months. They may prefer he finishes out the season with them and use the next six months to gather intel on a potential offseason deal. The market could improve by then, and there are also fewer restrictions than in a midseason trade. For example, teams could make imbalanced trades in the offseason since they could carry up to 21 players at a time.
Antetokounmpo will need to expand his list of preferred destinations to more than just the Knicks for the Bucks to consider trading him now. He may get his wish, but he doesn’t have much leverage to force a trade there since the Knicks won’t have cap space to sign him or enough apron space to sign and trade for him in 2027. On the other hand, he could probably force his way to the Nets or one of the Los Angeles teams since they can create maximum cap space then.
We still have a way to go before Antetokounmpo potentially gets traded. He is effectively in pre-agency with one guaranteed year left on his contract, so he can put his thumb on the scale. But the Bucks will have their work cut out for them in the post-Giannis era.
Catch up on last week’s content on Third Apron media!
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