Gary Trent Jr. signing continues trend of overpaid Milwaukee Bucks

It seems like the Milwaukee Bucks have constantly found themselves in the headlines so offseason, whether it's for good or for worse.

Of course there was the massive trade involving the Bucks sending Giannis Antetokounmpo to the Miami Heat, but recently another move by Milwaukee has gotten people's attention.

The Bucks decided to bring back guard Gary Trent Jr. Saturday afternoon, on a four-year, $64 million deal.

Free agent guard Gary Trent Jr. has agreed to a four-year, $64 million deal to stay with the Milwaukee Bucks, Klutch Sports CEO Rich Paul and agent Lucas Newton tells ESPN. pic.twitter.com/hZMDvuA816
— Shams Charania (@ShamsCharania) July 11, 2026

A surprisingly large deal for player who only averaged 8.1 points per game on 38.7% shooting from the field in 65 games. Trent's minutes and production has taken a dip in his second season with Milwaukee, and now returns to a jam-packed guard room.

The decision to add another guard to a team that has multiple guards was questionable, but on a fully guaranteed deal worth $64 million with no options is confusing.

Looking at other deals around the league, shooters such as Tim Hardaway Jr. or Luke Kennard who were more productive than Trent last season, signed for less.

It's not the first time the Bucks made an offseason move that left people scratching their head, as the deal has brought up memories of other shocking deals that the Bucks have made over the years.

Matthew Dellavedova - Four years, $38.4 million

In 2016, Milwaukee brought in guard Matthew Dellavedova on a four-year, $38.4 million deal after he just came off of winning the NBA Finals with the Cleveland Cavaliers. It was through a sign-and-trade that sent the draft rights of Albert Miralles and cash considerations to Cleveland.

The gritty Australian made a name for himself during the 2015 playoffs by taking on the assignment of guarding MVP Stephen Curry in the Finals, and did everything in his power to try and slow him down.

His effort caught the eyes of the Bucks, and they decided to pay a solid price for the guard. Dellavedova played for Milwaukee for three years and averaged 6.0 points, 1.8 rebounds and 4.2 assists per game.

While it was a career high tenure for him with the Bucks, Dellavedova was nothing more than a backup in his time, and he was eventually traded back the Cleveland in a three-team trade that also involved the Washington Wizards.

The Bucks would receive George Hill, Jason Smith, and a 2021 second-round pick and after three years, Dellavedova's time was finished in Milwaukee.

Miles Plumlee - Four years, $52 million

In that same offseason, the Bucks also threw a sizable contract to center Miles Plumlee to bring back to Milwaukee after acquiring him in a three-team trade during 2015. He appeared in 19 games for the Bucks in first season and averaged 3.2 points and 2.4 rebounds per game.

After averaging only 3.2 points per game, Milwaukee decided to extend Plumlee and signed him to four-year, $52 million contract.

The salary cap in 2016 had a massive increase that year, and as a result, multiple role players such Plumlee and Dellavedova signed big contracts. Plumlee would only play in 93 more games for the Bucks before he was traded in 2017 to the Charlotte Hornets for Spencer Hawes and Roy Hibbert.

Dan Gadzuric - Six years, $36 million

Milwaukee drafted Dan Gadzuric in the second round with the No. 34 overall pick from UCLA. In his first three seasons he averaged, 5.8 points and 5.9 rebounds per game, while shooting 52.5% from the field.

After averaging career-high 7.3 points, 8.3 rebounds and 1.3 blocks per game in that third year, the Bucks decided reward the big man with a six-year, $36 million contract.

However, the regression for Gadzuric came right after he inked the new deal and with the addition of the No. 1 overall pick in Andrew Bogut, the production the Bucks got in the few years prior started to decrease.

He continued to play for Milwaukee for the next five seasons where he would only average, 4.2 points and 3.5 rebounds per game. Gadzuric, would later be traded to the Golden State Warriors in 2010 along with Charlie Bell, in exchange for Corey Maggette and a second-round draft pick.

And of course, there was the decision to waive guard Damian Lillard in 2025 and stretch the remaining $113 million of his contract over the next five seasons to sign center Myles Turner to a four-year, $107 million deal.

Turner just finished his first season with the Bucks where he averaged 11.9 points, 5.3 rebounds and 1.6 blocks per game, on 44% shooting from the field and 38.3% from three.

While Turner is still on the roster, the center has been involved in trade talks after Antetokounmpo was traded to the Heat.

The Bucks have overpaid for players in the past, and it looks like Trent could be another example for the franchise.

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