Worst 2026 NBA Free Agent Signings: Bucks’ Bizarre Gary Trent Jr. Deal Leads List

NBA free agency isn’t the monumental event it used to be on the league’s calendar. The biggest superstars in basketball no longer hit the open market like they once did and the balance of power tends to shift on the trade market rather than during the free agency period. Overall, teams have also gotten way smarter about which players they spend big money on. This offseason proved teams are more cognizant than ever of how long they’re willing to spend big money on those players, too, with numerous free agents signing contracts that are only guaranteed through the first year or so.

In fewer words, long gone are the days of GMs throwing around money like candy as they try to build out their roster in free agency. We just don’t see $50 million forked over to a Tyler Johnson anymore, or $75 million to an Allen Crabbe. Front offices are more risk-averse and far less willing to bet piles of money on potential when it comes to free agents.

That does not mean every signing is a home run nowadays, however. While there were some great deals struck in 2026 free agency, there were a few that stood out as particularly questionable signings—whether it was due to the overall value of the deal, a player’s fit on a roster or a combination of the two. These deals won’t age as poorly as their predeccesors due to the new free agency environment, but there’s a very real chance they are remembered as mistakes nonetheless.

With free agency largely over (outside of the looming LeBron James decision), let’s dig into the worst signings of the 2026 offseason so far.

Gary Trent Jr., Milwaukee Bucks

Contract: Four years, $64 million

Trent’s deal came late in free agency and was, by far, the biggest head-scratcher of this year’s signings. The Bucks are in for a few bad seasons as they pick up the pieces from the end of the Giannis Antetokounmpo era so giving a bad contract to Trent is not really a big problem. He may even offer a valued locker room voice Milwaukee wanted to retain as it enters a period of transition. There are a lot of ways to explain why the Bucks bothered to keep him around. But for this price? It’s genuinely baffling in every way.

In 2025–26, the 27-year-old Trent had his worst NBA season since becoming a regular rotation player. He averaged 8.1 points, shot below 40% from the field and pulled down exactly one rebound per game while playing over 20 minutes. Do you know how hard it is to be out there for that long and only find one rebound? Professional basketball players can trip and fall into more rebounds than that. Defensively, he suffered a down year too. Of the 159 players who averaged at least 20 minutes per game and appeared in 60 games last year, Trent ranked 149th in defensive win shares. The only thing Trent did at an NBA level was shoot the three; he hit 36% of his 5.3 triples per night.

In light of all those numbers it’s no exaggeration to say the Bucks re-signed one of the worst role players in the NBA. Which, again, wouldn’t have been a big deal if the salary was low. But instead, Milwaukee felt it necessary to pay him an AAV on par with players like Mitchell Robinson, Tobias Harris and Max Strus—flawed players, but ones with defined NBA skills that have contributed to winning. The Trent deal was so bizarre it led to NBA media members wondering aloud if the league should be investigating the propriety of this deal. That’s usually not a good sign.

A confounding free agency decision that will be remembered as one of the most inexplicable of this era.

Marcus Smart, Houston Rockets

Marcus Smart and Kevin Duran — Smart will be teammates with Kevin Durant next season. | IMAGN IMAGES via Reuters Connect

Contract: Two years, $13 million

Smart is a great fit under Ime Udoka’s defense-first vision. There’s no denying that. But the question I would pose: did the Rockets really need another defensive-minded guard with erratic ballhandling skills?

Of course they didn’t. Houston lost to Smart and the Lakers in the first round because the roster had almost zero shooting or threatening offensive players in general around Kevin Durant. Defense was not the problem—scoring the ball was. Smart offers numerous positive qualities on and off the court but scoring is not exactly one of them. The veteran guard scored 9.3 points and shot 33.1% from deep (as well as only 39.5% overall from the field) last season in Los Angeles while playing alongside three elite offensive talents. It seems pretty unlikely those numbers will get any better with only KD to pull away attention from opposing defenses.

Smart is capable of organizing the offense at this stage in his career but any reps he gets in that regard will only take away from Amen Thompson and Reed Sheppard’s opportunities. Unless, of course, Udoka makes it a point to ensure the young guys get first priority. But his track record at the end of the bench suggests the opposite will happen.

If the Rockets are going to compete, the team needed an injection of offensive firepower. Barring that, the young talent on the roster needs room to grow—a chance to become what Houston is missing through experience and touches. The Smart signing fails to check either box and could prove more damaging to the latter goal than his relatively low salary number would suggest.

Kevin Huerter, Detroit Pistons

Contract: Three years, $27 million

The perception of Huerter is lagging behind his actual play. The veteran wing has been viewed as an archetypical three-and-D role player who isn’t elite in either regard but is at least passable. Which is what made him a solid acquisition by the Pistons at the deadline and a reasonable target to retain in free agency given the team’s overwhelming shooting struggles in the playoffs.

But Huerter doesn’t actually shoot the three that well. He hit 36% of his tries from beyond the arc in 2023–24 but has been on a downward trajectory since then, bottoming out with a 30.8% mark last year. His attempts have decreased with his make percentage. Huerter hasn’t been anything resembling a deadeye shooter in four seasons and offers little on the margins as a rebounder, passer or defender. Yet the Pistons, who won 60 games in the regular season but proved well short of contending status thanks to their offensive woes, gave him $9 million a year anyway as their highest-paid bench player.

Having him around isn’t awful basketball sense. Huerter is a passable connective piece on both ends most nights and at least showed at one time the abilty to be a real threat from beyond the arc. Every team needs dependable veterans off the bench who won’t actively hinder winning efforts. But it’s not clear who Detroit was bidding against with this contract. Huerter is a minimum-salaried player making three times that for unclear reasons.

Norman Powell, Chicago Bulls

Contract: Two years, $45 million

Like the Bucks above, the Bulls are focused on the future but had money to spend this offseason so they gave Powell a sizable deal. It wasn’t a signing made to elevate Chicago to contention. Nevertheless, it’s a lot of money to give a fringe All-Star player, one whose shoot-first tendencies don’t really benefit the young core of the roster.

In a vacuum, Powell has actually earned a $22.5 million salary after the last few years. The veteran has turned into one of the league’s more reliable scorers at the guard position and scored 21.7 points per game on quality efficiency for the Heat last season. He doesn’t contribute much else on the floor and fell out of Erik Spoelstra’s starting lineup by the end of the year but he is undeniably talented when it comes to the main goal of the game: putting the ball in the hoop.

Chicago is just a weird place for him to land. The Bulls are fully embracing the youth movement with Josh Giddey, Matas Buzelis and Caleb Wilson. Giddey already dominates the ball as a great passer who can’t shoot; Buzelis and Wilson will need touches as often as possible to reach their potential. Powell will give them all some extra space to work with but that could have been accomplished in myriad, cheaper ways. He isn’t going to set up his younger teammates with great passing, nor is he a career defender who can pass along tips of the trade.

This smells like a signing Chicago made just to put butts in seats. Which is fine given the money would have gone unspent otherwise. But is it worth the cost of possessions that will be centered around Powell instead of the team’s prized lottery pick and noted developmental project in Wilson? And was it really worth a $45 million commitment through 2028? We don’t think so.

More NBA From Sports Illustrated

Listen to SI’s NBA podcast, Open Floor, below or on Apple and Spotify. Watch the show on SI’s YouTube channel.

Add us as a preferred source on Google