The Bucks brought Tyler Herro back to Milwaukee last week before the NBA Draft, but that may not be the end of the story.
There’s already a strong sense that the Milwaukee native could be on the move again. The Bucks were said to have interest in bringing a third team into talks for Herro before they shut down trade discussions that weren’t directly between Miami and Boston. Now the expiring $33 million shooting guard sits in a spot where he should draw real attention on the open market, though the short term on his deal could make teams cautious about paying up.
If Milwaukee does decide to move him, there are a few paths that make some sense.
Toronto is one possible fit. The Raptors could use another ball handler who can create for himself and for others, especially after taking Allen Graves out of Santa Clara in the 2026 NBA Draft and then using a late second-round pick on Arizona senior point guard Jaden Bradley.
In that framework, the Bucks and Raptors could work out a deal built around Tyler Herro and Kevin Porter Jr. going to Toronto, with Milwaukee getting Immanuel Quickley, Gradey Dick, and a second-round pick back. Quickley is under contract for the next three seasons, while Dick is on an expiring deal and fell out of Toronto’s playoff rotation.
The Raptors could also look to move on from RJ Barrett for Kawhi Leonard if they had Herro at the two and Porter Jr. at the one.
New Orleans is another team that could come calling. The Pelicans are in that messy middle where they could either try to build something stronger or break pieces off and collect assets.
In this scenario, they’d be buying low on Herro and imagining a Dejounte Murray-Tyler Herro backcourt. The trade idea sends Herro to New Orleans, while Milwaukee gets Jordan Poole and three second-round picks in 2030, 2031, and 2032.
The Bucks wouldn’t have any interest in keeping Poole long term, so they could buy him out, waive him, or hold the contract until the trade deadline and then flip him for another player or two if a team needs salary relief. If that happens, the team taking on the expiring money would probably need to add more second-round picks.
Denver offers a much bigger swing. The Nuggets are looking for a move that changes the look of their roster, and this one would do it.
In that deal, Denver gets Tyler Herro, A.J. Green, Kevin Porter Jr. and Jericho Sims.
Milwaukee would receive Cameron Johnson, Christian Braun, Zeke Nnaji, a 2031 first-round pick swap, and a 2033 second-round pick. The Nuggets would be reshaping their wing group, sending out Johnson and Braun for three guards and a center.
Sims gives them a useful depth center with athleticism, Herro and Porter Jr. bring shot creation, and A.J. Green would get a big boost playing next to Giannis, with the floor spacing now working alongside Nikola Jokic.
Johnson’s expiring deal could carry value at the deadline, Braun still has four years left and is only 25, and the 2031 pick swap could matter a lot if Denver is without Jokic by then.
Then there’s Portland, which just changed its guard picture in a major way. On Monday afternoon, the Trail Blazers acquired Memphis’ Ja Morant, and Shams Charania reported that Portland was out on Jaylen Brown, with Morant being the big move.
That leaves the Blazers with Ja Morant, Jrue Holiday, Damian Lillard and Scoot Henderson on the roster, and if they want to get deeper into the playoffs, moving one of those point guards for a shooting guard starts to make sense. In the proposed deal, Milwaukee would get Jrue Holiday plus a 2027 second-round pick and a 2029 second-round pick, while Portland would land Herro.
That would bring a familiar face back to Milwaukee and give the Bucks two more second-rounders. For Portland, it would turn four point guards into three and add a proven scorer and former All-Star.
Holiday’s defense and leadership would also give the Bucks a veteran voice for newly drafted Nate Ament and Brayden Burries, and he still has two years left on his deal plus a player option for 2027-28.
Milwaukee doesn’t need to rush anything. If the right Herro deal comes along, the Bucks should consider it, but the market could shift once free agency settles and more players become available.
There’s also a real chance Herro ends up fitting with the Bucks for the next few years and becomes the veteran presence for this new-look group. However this plays out, he’s one of the most interesting names to watch in Milwaukee this offseason and into the season.
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