3 Milwaukee Bucks Who May Not Survive The Trade Deadline

Milwaukee Bucks general manager Jon Horst is reportedly working the phones like a man possessed ahead of the NBA trade deadline.

The problem is he’s running out of time, running out of options, and—thanks to the NBA’s new collective bargaining agreement—running out of ways to make a deal happen.

The trade deadline is fast approaching—Thursday, February 6 at 2 p.m. Central—and the Bucks’ financial situation is a mess. Milwaukee is currently $6.5 million over the second apron, which is a massive problem under the new CBA.

For starters, that means they can’t aggregate salaries in a trade. No package deals, no three-for-one swaps. Any deal they make has to be a straight-up, one-for-one swap. That’s a nightmare for a team that desperately needs roster upgrades.

There is a workaround. The Bucks could shed enough salary to get under the second apron, which would allow them to aggregate contracts again. The catch is once they’re under, they have to stay under for the rest of the season, meaning no buyout signings and no two-way contract conversions that push them back over.

Staying above the second apron has long-term consequences, too.

The Bucks are jeopardizing their 2032 first-round pick by staying over the second apron. The new CBA says any team that ends the season over the second apron has its first-round pick frozen seven years in the future. This means they couldn’t trade the selection.

Even worse, Milwaukee would have to finish three of the next four seasons below the second apron to unfreeze that pick. If they don’t, their first-round selection falls to no. 30 in that year’s draft. That’s not ideal for an aging team whose current stars will be way out of their prime by then.

All of this is happening while the Bucks are free-falling in the standings.

Entering Wednesday, Milwaukee is sitting in fifth place in the Eastern Conference, just two games away from the play-in. It’s clear this roster isn’t working as expected.

So, between the financial chaos and the on-court struggles, something has to give. Here are three Bucks who may not survive the trade deadline.

Pat Connaughton

From a financial standpoint, trading Pat Connaughton is the cleanest way for the Bucks to get under the second apron. His $9.4 million salary is right in the sweet spot—dumping it would give Milwaukee the breathing room it needs.

But if it were that easy, Connaughton would already be gone.

For starters, he has a player option for the 2025-26 season worth another $9.4 million. Given how much his production has dropped off, there’s no way he’s declining that option. Any team trading for him has to commit to paying him next year, too.

That’s already bad enough, but it gets worse.

The Athletic’s Eric Nehm reported that league executives estimate it would take three or four second-round picks—or a late first-rounder—just to get rid of Connaughton’s contract.

That’s draft capital the Bucks simply don’t have. The only tradeable picks Milwaukee owns are its 2031 first and second-round selections. If they want to move Connaughton, they have to either attach one of those picks or find a team willing to take on his deal for nothing.

As motivated as the Bucks are to trade him, the odds aren’t great. But if a deal happens, Connaughton is probably the first to go.

Bobby Portis

The Bucks have felt the absence of Bobby Portis in a big way over the past few weeks. Portis has missed six straight games due to personal reasons, leaving Milwaukee with just two bigs—Brook Lopez and Giannis Antetokounmpo.

Uncoincidentally, the Bucks have gone 1-5 in that stretch. Their defense has cratered, their rebounding has taken a hit, and their bench production has plummeted.

If the Bucks are going to trade Portis, they absolutely have to get a big man in return. Not just any big, but an athletic, versatile big who can play alongside both Giannis and Lopez.

That’s been the biggest issue with Portis—he’s a great bench scorer, but defensively, he’s not a natural fit in Milwaukee’s system.

There’s also the contract situation. Portis has a player option for $13.4 million next season, which he’s likely to decline in search of a bigger payday. If the Bucks don’t think they can—or should—pay him, they could try to move him now rather than risk losing him for nothing.

Khris Middleton

This one would hurt. Badly.

Khris Middleton has been everything for the Bucks over the past decade. He arrived as a throw-in from Detroit, grew into an All-Star, helped deliver a championship to Milwaukee, and has been a steady presence through every phase of the franchise’s rise.

But the reality is brutal—Middleton is a shell of his former self.

He still has moments where he flashes his old brilliance, but far too often, he looks slow, ineffective, and defensively vulnerable. He simply can’t create his own shot the way he used to, and defensively, he’s become a liability.

If the Bucks want to make a big move—someone like Jimmy Butler, for example—Middleton’s contract has to be involved.

He’s making $31.7 million this season, with a player option worth $34 million next year. That’s a massive number for a player who isn’t close to the All-Star he once was.

Trading Middleton would be gut-wrenching for Milwaukee. But if the Bucks are serious about making one final big swing in this era, it might be the only move that truly changes their trajectory.