Should Milwaukee Trade Tyler Herro? 4 Ideas to Move the Bucks' Newly Acquired Guard

The Milwaukee native was traded back to his hometown last week before the NBA Draft, but there is a strong belief that he could once again be on the move. The Bucks were rumored to have interest in bringing in a third team to acquire Herro before they shutdown trade talks that weren't directly between Miami and Boston.

Now the expiring $33M shooting guard is going to have decent value on the open market, but because his contract is only for the remainder of the season, team's might be hesitant to spend a lot for his talents.

Here are four trades that I think could make sense for the recently acquired shooter.

Toronto Raptors

Apr 9, 2026; Toronto, Ontario, CAN; Miami Heat guard Tyler Herro (14) drives to the basket against Toronto Raptors guard Jamal Shead (23) during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

The Toronto Raptors are a team that could use another ball handler that can create for himself and for others. In the 2026 NBA Draft, the Raptors walked away with another wing in Allen Graves out of Santa Clara, and late in the second round selected Jaden Bradley, the senior point guard out of Arizona.

Here is the trade idea that the Bucks and Raptors could make, especially after having rumored interest in Ja Morant, who was recently traded to the Portland Trail Blazers, and LaMelo Ball, who recently swapped to the Minnesota Timberwolves.

Trade Idea

Toronto Receives: Tyler Herro and Kevin Porter Jr.

Milwaukee Receives: Immanuel Quickley, Gradey Dick, and a second-round pick

Quickley is under contract for the next three seasons and Gradey Dick is on an expiring contract and fell out of the Raptors playoff rotation. The Raptors could then look to move on from RJ Barrett for Kawhi Leonard if they have Herro at the two and Porter Jr,. at the one.

New Orleans Pelicans

The New Orleans Pelicans are one of the most confusing teams in the league as they can either try and build a stronger team, or sell off on some of their better pieces and acquire assets.

In this trade scenario, they are buying low on Tyler Herro and looking at how a Dejounte Murray/Tyler Herro backcourt duo would look. Here is the trade:

Trade Idea

Milwaukee Receives: Jordan Poole and three second-picks in 2030, 2031, and 2032.

New Orleans Receives: Tyler Herro

The Bucks make this move because they get three valuable second-round picks from the Pelicans, a team that is looking to bolster their depth with this group. The Bucks have no desire to retain Jordan Poole, so they can choose to buy him out, waive him completely, or hold onto his contract up to the trade deadline, and then trade him for a player or two that a team wants to offload for salary cap relief. The team looking to offload salary for the expiring deal will likely have to add more second-round picks.

Denver Nuggets

The Denver Nuggets are a team that is looking to make a move and there is one trade idea that makes sense for them to get better and gives them a different look

Trade Idea

Denver Receives: Tyler Herro, A.J. Green, Kevin Porter Jr. and Jericho Sims

Milwaukee Receives: Cameron Johnson, Christian Braun, Zeke Nnaji, a 2031 first-round pick swap, and a 2033 second-round pick

The Denver Nuggets get off their wing core of Cameron Johnson and Christian Braun for three guards and a center. Sims is a solid depth piece center with athleticism, Herro and Porter Jr. are two ball handlers who can also score on their own, A.J. Green's world goes from good to great after playing alongside Giannis, he now gets to space the floor with the best passer in the NBA, Nikloa Jokic.

Johnson is an expiring contract that will likely have a good amount of value at the trade deadline for a team looking for wing depth. Christian Braun's contract is lengthy with four years remaining, but he's 25 years old and still has plenty of room to grow as a player. They also get a 2031 first-round pick swap from Denver for this move, and there is a world where the Nuggets are without Jokic in that season, making the ability to swap picks that season extremely valuable.

Portland Trail Blazers

On Monday afternoon, the Portland Trail Blazers acquired Memphis' Ja Morant, adding yet another point guard to their team. The latest reporting from Shams Charania, ESPN insider, was that the Trail Blazers were out on trading for Jaylen Brown, and that Morant was their big move.

This means that Portland now has Ja Morant, Jrue Holiday, Damian Lillard and Scoot Henderson on the roster. As Portland is looking to get better and make it deeper into the playoffs, trading one of their point guards for a shooting guard makes good sense.

Trade Ideea

Milwaukee Receives: Jrue Holiday, a 2027 second-round pick, and 2029 second-round pick

Portland Receives: Tyler Herro

This move brings a franchise favorite back to the city of Milwaukee, and gives the Bucks two more second-round picks. Portland turns four point guards into three, and adds a terrific scorer and former All-Star.

Holiday's defensive minded approach and leadership will help mentor young players in Milwaukee, especially the newly drafted Nate Ament and Brayden Burries. He has two years under contract, and a player option for the 2027-28 season. Team's that are looking to win-now could also have intrigue in Holiday at the trade deadline.

Final Thoughts

If Milwaukee finds the right deal for Tyler Herro they should strongly consider trading him, but should not rush to make a move. Once free agency settles, there could be more players available that make sense for the Bucks to offload Herro for.

There is also a world in which Herro fits with the Bucks for the next handful of years and could be the veteran for this new-look team. What the Bucks do with the local standout will be one of the more fascinating stroylines to watch this offseason and season.

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