As the NBA’s Feb. 6 trade deadline approaches, few teams are working the phones as hard as the Milwaukee Bucks. Tim Bontemps and Brian Windhorst categorized the Bucks’ deadline desperation as “high,” while Marc Stein reported that they are “as determined as any team on the NBA map” to make a deal.
The Bucks’ eagerness to improve the roster should come as no surprise. Not only is general manager Jon Horst one of the most aggressive executives in the league — as Bobby Marks points out, Horst has made 28 trades since he started the job back in 2017 — but the team’s title window with Giannis Antetokounmpo, Damian Lillard and an aging supporting cast is closing.
The Bucks have won just one playoff series since their championship in 2021 and have been eliminated from the last three postseasons due to injuries: Khris Middleton in 2022, Antetokounmpo in 2023, and Antetokounmpo and Lillard in 2024. This only makes this season more important.
Unfortunately for the Bucks and Horst, it may not be so easy for them to find the kind of deal they want. With just a week remaining until the deadline, let’s take a closer look at where the Bucks stand.
Second-apron issues
The NBA and the NBPA agreed to a new collective bargaining agreement in 2023, which has brought about a number of changes, both on and off the court. One of the biggest in regard to team building is the second apron of the luxury tax, which has added further handicaps to teams with expensive rosters.
That includes the Bucks, who are one of four teams, along with the Boston Celtics, Minnesota Timberwolves and Phoneix Suns, sitting above the second apron of $188.9 million. As a result, the Bucks, and those other teams, have restrictions on what kind of trades they can make:
- The Bucks cannot aggregate salaries to make a trade.
- The Bucks can only take back 100% or less of the salary they send out in a trade.
- The Bucks cannot send out cash in a trade.
That is particularly restrictive for the Bucks, given their salary allocations. Antetokounmpo and Lillard aren’t going to be traded, and only four other players — Khris Middleton, Brook Lopez, Bobby Portis and Pat Connaughton — make more than $2.7 million.
They’ve been most heavily linked to stars such as Jimmy Butler, Zach LaVine and Bradley Beal, but because those players’ salaries are all higher than anyone on the roster save for Antetokounmpo and Lillard, the Bucks cannot actually trade for them at this time.
It seems unlikely they’d move Middleton for someone lesser than that, and likewise, it’s hard to imagine Lopez being dealt, given his importance to their floor spacing and rim protection. Would anyone be interested in Portis? Perhaps, but finding an actual upgrade via a one-for-one trade may be difficult. The same applies to a host of players making $2.7 million or less.
Connaughton to the rescue?
There is an escape plan for the Bucks, though executing it may be difficult. Between salary and potential bonuses, the Bucks are at $195.4 million, which is $6.5 million over the second apron. If they can shed salary to get below the second apron, they would then be allowed to aggregate salaries in a trade.
Their preferred route to doing so would be dumping Connaughton, who is making $9.4 million but fell out of the rotation for nearly two months and is having his worst season since arriving in Milwaukee. Whether the Bucks can find someone to take Connaughton off their hands remains to be seen.
The 32-year-old swingman has been on the decline for a few years and has a $9.4 million player option for next season that he will certainly pick up. A team willing to absorb Connaughton into their cap space would want something for their trouble, especially since he’d be under contract for next season as well.
However, the Bucks don’t have much to offer since they cannot aggregate salaries at this point to add a young player to the deal. Their only other assets are a 2031 first-round pick and a 2031 second-round pick.
There’s no way the Bucks would give up their 2031 first — one of the most valuable future firsts in the entire league — just to dump Connaughton’s salary. If they wanted to get crafty, they could try to trade that first to another team in exchange for multiple first-round picks, à la the recent Phoenix Suns trade. That might give them some more flexibility, but there’s no guarantee they could find such a deal.
Otherwise, it becomes a question of whether their 2031 second is enough to entice a team. To which the answer is… maybe?
Side note: Do you think Horst wishes right now that he could have back the five second-round picks he traded in 2023 for 32-year-old Jae Crowder, who wound up playing 68 games for the franchise?
The million-dollar Middleton question
Let’s say the Bucks are able to find a team to take Connaughton’s salary and they sneak under the second apron, allowing them to package multiple players together for one of the aforementioned big names. Middleton would have to be in such a trade. It’s clear the Bucks have discussed that possibility, but would they actually trade him?
That’s the million-dollar question that could decide their title hopes, not only this season but next.
The case for trading Middleton
Since spraining his knee in the 2022 playoffs, Middleton has only played 120 games between the regular season and playoffs. During that time, he’s undergone numerous surgeries, including procedures on both ankles last summer that cost him the first 21 games of this season. His ankles are an ongoing issue and he remains on a minutes restriction and has been removed from the starting lineup.
Middleton has gone scoreless in two of the Bucks’ last three games and three times in 21 appearances this season — the only three times in his entire career in which he’s played at least 15 minutes and failed to score. Between his health problems and the Bucks’ decision to gear the offense toward the Antetokounmpo-Lillard two-man game, Middleton has become something of an afterthought at times.
Doc Rivers explains why the Bucks are benching Khris Middleton despite his impressive numbers as a starter
Jack Maloney
While the Bucks have certainly played better since their awful 2-8 start, it’s hard to see them winning four consecutive playoff rounds with Middleton in this state. Is he going to be able to play 25-30 minutes per game, every other night for two months during the playoffs? We’ve seen no evidence to say yes. If they can flip him for someone like Butler, LaVine or Beal, that could give them a better chance to contend this season.
The case against trading Middleton
No one has played more games with Antetokounmpo than Middleton. And while past performance shouldn’t always determine what a team does in the present, the institutional knowledge Middleton possesses should not be overlooked. One of the many reasons that last season went wrong for the Bucks is they tried to change too much in too short of a time, and they never got on the same page. Making another blockbuster trade to send out someone with an innate connection with arguably the best player in the world would be another setback for the team’s chemistry, both on and off the court.
Furthermore, Middleton’s postseason history has to be taken into account. They won’t win the title in 2021 without his heroics — both in the Eastern Conference finals when Antetokounmpo was injured and during the Finals — and he showed on multiple occasions last season that he’s capable of rising to the moment even when he’s less than 100% healthy. Sure, Butler has an impressive playoff resume, but LaVine has played four career playoff games and Beal has never been beyond the second round.
Finally, while it’s true that Middleton has had a few stinkers, he’s also had some terrific games and has largely been productive. He’s still a reliable 3-point shooter, an underrated playmaker and helps organize the team. Since he’s returned to action, the Bucks have a plus-5.8 net rating with him on the floor (they are plus-3.4 with Lillard in that same span). As his ankles get stronger and he becomes more accustomed to his new role, his level of play should only improve.
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