The Milwaukee Bucks front office is currently trying to spin a masterclass in roster-building contradiction. Per a report by Spotrac's Keith Smith, a Bucks executive made the organization's extension priorities crystal clear when it comes to keeping their big haul in Tyler Herro, which is absolutely head-scratching when you consider the deal they just absorbed from Gary Trent Jr. and his camp.
“That’s something we’ll talk about with his reps. We’d love to get something done, provided it makes sense for both Tyler and us,” a Bucks front office executive said of both Herro and Jaime Jaquez Jr. “For Jaime, it’s the same thing. He’s in a different spot because of restricted free agency. But, in an ideal world, you get those things taken care of now. That way everyone can just play the season without the future weighing on them."
Milwaukee's Tyler Herro plans make zero sense along with Gary Trent Jr. signing
Wanting to lock down a 26-year-old scorer makes a certain degree of sense in a vacuum. But when you zoom out and look at the financial and roster carnage left behind by the Gary Trent Jr. signing, that stance on Herro starts to look downright indefensible.
The Gary Trent Jr. deal already didn't make sense from the start after the season he just had with Milwaukee. After an excellent campaign the year before as a flamethrower from behind the three-point line, Trent had the worst statistical season of his career in 2026 with the Bucks, averaging just 8.1 points per game on 38.7 percent shooting from the field. It was, by all accounts, an absolute dud of a season, punctuated by his eventual removal from Doc Rivers' rotation by season's end.
So it should come as no surprise that fans were up in arms over his four-year, $64 million extension with Milwaukee, which is now being investigated by the association, and rightly so. But compounding matters even worse is that Trent's presence will likely take away opportunities from the young Bucks, who are, according to Smith's report on Spotrac, the future of the franchise.
“We’ve got a lot of vets who are going to play. But behind them are kids who are going to push them. We should have a really competitive camp this year. From talking to the guys, everyone feels energized and ready to go. We’re excited to get back to work already in the fall," one Bucks executive was quoted as telling Smith.
Herro and Trent Jr. may take away from the development of young Bucks guards
If the Bucks are keeping both Trent and Herro in town, that can only mean fewer shots for the likes of Burries, Jakucionis, and Rollins, which goes against everything a rebuild is supposed to be about. Burries in particular should have already forced the Bucks into a difficult decision concerning Herro, and this stance is the total opposite of what this writer would have expected.
Keeping Herro around instead of flipping him for more assets would have been easier to swallow without Trent Jr.'s monster deal, considering he's already endeared himself to fans with his familiarity with team lore. But with Trent, it's just hard to justify for a team that should be dead set on developing young talent as much as possible.
Of course, having both guards, who are the closest the team now has to established veterans, can also help by way of mentorship for these young guards still finding their footing in the league. But the reality is that Milwaukee has been staring at a logjam in their backcourt for a few weeks now. And with training camp upon us, there's still little that indicates the front office has found clarity on what to do about that.
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