Tyler Herro does not seem like an obvious match for a rebuilding team like the Chicago Bulls, but look a little closer and the fit becomes clear: The Bulls desperately need Herro's shot creation, and they field a roster uniquely suited to cover for his defensive shortcomings.
It's a trade that would actually make sense for Herro, Chicago and the Milwaukee Bucks.
Milwaukee landed Herro as the centerpiece of the deal that Giannis Antetokounmpo to Miami. The 26-year-old, who grew up about 12 miles away from Fiserv Forum, has averaged at least 20 points and four assists since his his third year in the NBA. He has a Sixth Man of the Year Award and an All-Star berth under his belt.
He's also, however, missed significant chunks of time due to injury, is a liability on defense and is due a hefty payday this summer. It's not hard to see why the Bucks aren't sold on keeping him long-term.
The Bulls should have fewer concerns.
Tyler Herro makes sense with the Chicago Bulls roster
Any argument for a Herro trade — or any trade, really — comes with an obvious disclaimer: The Bulls are in the early stages of a lengthy rebuild project, and any win-now move would be irresponsible. But Herro fits nicely with Chicago's roster right now, and he still will five years from now.
Outside of Josh Giddey and 33-year-old Norman Powell, the Bulls are woefully short on playmakers and shot creators. Tre Jones can run an offense off the bench, Matas Buzelis is improving and ... well, that's pretty much it for now until/unless rookies Caleb Wilson and Dailyn Swain find their footing.
Herro would change the equation as soon as he stepped foot in the Windy City.
The former Kentucky star continues to develop into a three-level scorer. His field-goal percentage jumped from 44.1 percent in 2023-24 to 47.2 the following year and 48.0 percent last season. Over that same period, he shot 38.1 percent from three on an average of 8.1 attempts. He's an elite free-throw shooter who connected on 91.7 percent last season and 87.8 percent for his career.
It's also important not to overlook his emergence as a playmaker. Herro averaged a career-high 5.5 assists in 2024-25 when he played 77 games, and his assist-to-turnover ratio has improved each of the last five seasons.
His ability as a scorer and secondary playmaker would give the Bulls two things they don't have much of, and at 26, he's not wildly outside of Chicago's timeline; he should still be under 30 by the time the franchise is hitting the postseason again.
The Bulls can cover for Herro's weaknesses
Herro is, admittedly, a poor and slight defender who consistently gets targeted by opposing offenses. The Bulls have antidotes for that, however, in Buzelis and Caleb Wilson.
Buzelis is already one of the NBA's elite weakside shot-blockers; the 21-year-old finished sixth in the league in blocks last year, tied with Raptors forward Scottie Barnes, who's widely considered one of the game's premier defenders.
Wilson is a 6-foot-10 athletic freak (in a good way) who has the physical tools to be one of the most effective and versatile defenders in the league as a rookie.
That pair should be able to erase perimeter mistakes for the next decade-plus, as long as they stay healthy. They're ideal complimentary pieces to have alongside poor defenders like Herro and Giddey.
Acquiring Herro — and handing him a ton of money — would surely be a divisive move. But it actually makes more sense than you might think.
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