The Raptors have a clear lane if they want to shake up their guard rotation, and Tyler Herro looks like the kind of swing that could actually move the needle.
Milwaukee’s situation is awkward enough to make a deal possible. The Bucks are heading into the post-Giannis era with no first-round pick in the upcoming 2027 NBA Draft, no obvious next franchise player, and a pile of trade assets that don’t exactly scream long-term reset. That kind of spot can push a team toward taking on money and collecting draft capital, which is why Toronto should be paying attention if Bobby Webster wants to upgrade the roster this season.
Myles Turner had been the name most often tied to the Raptors, but Jakob Poeltl shut that conversation down in Toronto’s recent game against Milwaukee. Herro, though, is a different story. He’s the Bucks guard the Raptors should be chasing.
A healthy Herro would give Toronto more than just a new name at the position. He’d be a real step up from Immanuel Quickley as both a shooter and a creator, and he’d bring more punch when the ball is in his hands. That matters for a Raptors team that needs help everywhere it can get it on the perimeter.
The fit is easy to see. Toronto needs guard play that can stretch the floor, work on and off the ball, and hold up in the playoffs.
Herro checks those boxes. Quickley is sitting below 33 percent from three, while Herro is hitting 38.0 percent from deep this season.
For a Raptors team that ranks bottom five in three-point percentage, that kind of shooting would change the geometry of the offense. It would also make life easier for Toronto’s forwards and wings, opening more driving lanes to the rim.
The scoring gap is there, too. Herro is averaging 21.6 points, 4.1 rebounds, and 4.3 assists per game this season, which would be a clear boost over Quickley’s current output.
The obvious concern is that Herro isn’t a pure point guard, and that has already been part of the Quickley issue in Toronto. Still, Herro has handled point guard duties in stretches with the Heat, and he’s shown he can make plays. During his 2024-25 All-Star season, he averaged 5.5 assists per game.
From Milwaukee’s side, the logic would be simple: add draft capital and keep building around younger talent like Brayden Burries and Nate Ament. If Toronto is willing to attach a first-round pick to Quickley, that could be enough to get the Bucks to listen, even if they have to absorb his contract in the process. Herro has been a fun story for them, but if the goal is to set up the future, a first-rounder is the kind of return that gets attention.
There’s also the question of what comes next for Toronto if it makes the move. Trading for Herro would likely mean extending him after this season.
That’s the part that could make the Raptors hesitate. But Herro is in the prime of his career, and locking him in feels like a safer bet than chasing some of the older Quickley alternatives on the market and then paying them long term.
It isn’t a perfect deal. But if Toronto can upgrade Quickley’s spot for the price of one future first-round pick, that’s the kind of move worth considering.
In Other News...
Raptors Frontcourt Question Could Define Their Next Big Kawhi Era Move
The Raptors have already made their biggest splash by bringing Kawhi Leonard back from the Clippers, and now the conversation around the roster has shifted to what comes next. For a team trying to turn a headline move into a real push, the frontcourt has quickly become the area to watch, with the need for another impact big man hanging over the rest of the offseason.
One name that has surfaced in that discussion is Domantas Sabonis, the Kings center whose skill set would immediately change Torontos interior outlook if the two sides ever found common ground. Nothing has been confirmed, but the speculation alone says plenty about where the Raptors see their next opening, and whether they can pair Leonards return with the kind of frontcourt upgrade that makes the move feel complete. [Read more 🡒]
Gradey Dick Is Giving Raptors Fans A Tough Trade Debate
Gradey Dicks move from Toronto to the Clippers has turned into one of those deals Raptors fans cant quite stop revisiting. Since landing in Los Angeles during the 2025-26 season, hes found the kind of consistent run that was harder to come by in Toronto, helped in part by injuries on the Clippers roster, and the extra minutes have started to show up in his production.
The shooting numbers have climbed with the opportunity, including a career-high field goal percentage and a better touch from three-point range, which only sharpens the debate over what Toronto gave up and what it might have to consider later. Dicks contract is set to expire after this season, and with restricted free agency looming, his next step could end up mattering just as much as the trade itself. [Read more 🡒]
Raptors Face A Risky Dejounte Murray Question At Point Guard
Dejounte Murrays name has suddenly become part of the Raptors conversation, even though nothing is close to finalized. ESPNs Shams Charania reported that the Pelicans guard wants out of New Orleans and that his agent and team officials are working toward a resolution, which has naturally opened the door to speculation about where he might land. Phoenix has already surfaced as one possible destination, but the broader league chatter has also prompted a look at how Murray would fit in Toronto, where point guard remains a position the front office has to keep evaluating.
For the Raptors, the appeal is obvious enough: Murray brings a track record as a productive lead guard, and his profile would address a real need if the team ever got serious about adding another ballhandler. The complication is just as obvious, though, because his injury history and the uncertainty around his current situation make this a risky question rather than a clean fit. For now, it is still only a hypothetical, but it is the kind of hypothetical that tends to linger when a team is trying to sort out its long-term backcourt direction. [Read more 🡒]