The Milwaukee Bucks are in a tough spot as they enter the post-Giannis era. With no first-round pick in the upcoming 2027 NBA Draft, no clear next franchise player, and a ton of mediocre trade assets, Milwaukee faces a difficult rebuild. This could force the Bucks to absorb bad contracts to recoup assets and lay the foundation for a smoother rebuild. For the Toronto Raptors, this makes them a natural trade partner if Bobby Webster is looking to improve their roster this season.
Myles Turner was often a name linked to the Raptors as a potential trade target, but Jakob Poeltl put those talks to rest in Toronto’s recent game against Milwaukee. However, another Bucks player Webster and the Raptors' front office should be targeting is guard Tyler Herro.
The former All-Star has struggled to stay healthy over the past couple of seasons, but that hasn’t been an issue since he joined his hometown team. A healthy Herro would be a massive upgrade over Immanuel Quickley as a shooter and shot creator, while also providing a much stronger offensive presence with the ball in his hands.
If Toronto attached a first-round pick to Quickley, the Bucks would have a reason to consider it. While Herro has been a fun story for them, they need to position themselves better for the future, and adding draft capital is the best way to do that.
Tyler Herro could give the Raptors the Immanuel Quickley upgrade they need
When you think about what Toronto needs at the guard spot, a few things come to mind: knockdown shooting, the ability to play on and off the ball, and playoff experience. Herro checks all three of those boxes. Replacing IQ’s sub-33 percent three-point percentage with Herro’s 38.0 percent three-point clip would really help a Raptors team that is bottom five in three-point percentage. His gravity as a shooter could also open things up more for the Raptors' forwards and wings to get to the rim more easily.
From a general scoring and production standpoint, Herro’s averages of 21.6 points, 4.1 rebounds, and 4.3 assists per game this season would also be a big upgrade over IQ’s current production.
Obviously, the one thing Herro doesn’t have working for him is that he isn’t a natural point guard, which has been part of the issue with the Immanuel Quickley experience. However, during his time with the Heat, we saw him play point guard in stretches, and he’s always been a very capable playmaker, averaging 5.5 assists per game during his 2024-25 All-Star season.
For the Bucks, this deal would strictly be about adding more draft capital to bring in more young talent to surround Brayden Burries and Nate Ament. While it’s unclear whether Milwaukee views Herro as part of their future, Toronto offering a first-round pick could give the Bucks a compelling reason to move him, even if it means taking on Quickley's contract.
I understand on paper Herro for IQ doesn’t sound like a drastic upgrade, but we’ve seen Herro reach heights in his career that Quickley has flat-out never come close to. He'd also bring valuable playoff experience from his time with the Heat, including being part of two NBA Finals runs. The one hold-up from the Raptors side may be that trading for Herro would likely mean extending him after this season. But he’s also in the prime of his career, and committing to him long-term feels like less of a risk than trading for and extending some of the older potential IQ upgrades on the market.
It’s far from a perfect trade, but being able to upgrade Quickley’s spot at the cost of one future first-round pick would be worth it for the Raptors.
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