New Blockbuster Three-Team Trade Proposal Sends Tyler Herro To Boston, Anfernee Simons to Miami

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While there are still some notable restricted free agents out there, the NBA free agency period has settled down for now, and the landscape for the NBA is taking shape for next season.
After trading for Kristaps Porzingis and drafting Asa Newell, Atlanta reached a pair of huge free agent signings on the first day of the free agency period. The Hawks signed Wolves guard Nickeil Alexander-Walker to a four-year, $62 million deal in a sign and trade that sent a 2027 2nd-round pick (via CLE) to the Wolves. Then, the Hawks signed free agent guard Luke Kennard to a one-year, $11 million deal. Not only that, but they got an unprotected first-round pick from the New Orleans Pelicans in a draft-night trade. Given the massive injuries in the Eastern Conference next season, it seems that the Atlanta Hawks are going for it and making moves to put themselves in a position to contend. One area they could still use some depth is at small forward, a third center. or another ball-handler. They have one roster spot remaining after signing last year's second-round pick Nikola Durisic to a standard contract and reportedly signing Magic forward Caleb Houstan to a one-year deal.
Miami seems to be stuck in the middle, a place where most NBA teams don't want to be. They seem to be just good enough to make the playoffs as a lower seed, but they are not a real NBA Finals threat. They are also not bad enough to get a real valuable lottery pick either. The Heat seem to be trying to have as much money free as possible for the next couple of offseasons, but one move they might want to consider is moving Tyler Herro before his contract potentially makes him unmovable. Herro will be eligible to sign a three-year, $149.7 million extension on October 1, but if he passes on that extension, he could sign a four-year, $206.9 million extension during the 2026 offseason. It could also be bigger if he were to make All-NBA. Is he worth that contract? Will Miami want to offer him $206.9 million? Things could get dicey between the two and while it might seem crazy, could Miami go ahead and look to deal Herro? What is his trade value around the league? It might not be as high as you think, as the league seems to be low on the type of player that Herro is, which is a tremendous offensive player, but one that struggles on defense. Again, I don't think they move Herro, but it is not as crazy as it may sound.
Boston appears to be taking a gap year in 2025-2026. They are not tanking exactly, but they have cut costs to get under the second apron. With Jayson Tatum likely out for the upcoming season, Boston still has the talent to make the playoffs, but they are not championship contenders. Will they look for ways to continue cutting salaries to get further under the aprons? They have holes in the frontcourt to address and have been rumored to be shopping Anfernee Simons after acquiring him from the Trail Blazers in the Jrue Holiday trade.
So how about a trade where each of these teams tries to fill a need?
It should be noted that this is just a speculative and fun exercise to see what kind of moves can be made, not what I think the Hawks or any other teams should do or will do. That is all.
Hawks Receive: Sam Hauser
Celtics Receive: Tyler Herro
Heat Receive: Anfernee Simons, Jordan Walsh, an unprotected 2026 1st round pick swap (via BOS), and an unprotected 2027 1st round pick (via BOS)

Why the Hawks do this trade: They get one of the elite shooters in the NBA and round out their roster. Hauser is one of the best movement shooters in the NBA and would give Trae Young another elite shooter to put around him. That has been one of the Hawks objectives this offseason and getting Hauser would make their roster one of the best in the Eastern Conference.
Why the Hawks don't do this trade: This move would put them into the luxury tax and owner Tony Ressler has not paid it since becoming the owner. Hauser would fit the team perfectly, but are the Hawks willing to pay the luxury tax? That would be the only thing standing in their way.
Why the Celtics do this trade: They get Herro and set themselves up to make the playoffs this season and when Tatum comes back, they become the Eastern Conference favorites again. A lineup of Herro, Derrick White, and Jaylen Brown is a great trio to have and while this roster still has holes, they are undoubtedly better than what they would be with Simons.
Why the Celtics don't do this trade: It comes down to if the Celtics want to pay Herro an extension. Boston showed the willingness to have an expensive team if they are competing for a championship, but this roster still needs a lot of work at center and on the bench, even when Tatum comes back. They would be restricted in their finances if Herro gets the extension he wants, but maybe he takes a discount.
Why the Heat do this trade: This is about future flexibility. Simons is not as good as Herro, but he is fine as a one year stop gap. Miami gets two extra first-round picks to use in a trade if needed, but they continue to clear their finances for future years.
Why the Heat don't do this trade: Is this enough for Herro? These are not premium picks and Simons is unlikely to be a part of their future plans. They would get worse in the short term and unless there are premium free agents waiting to come to Miami, it would be unwise to move Herro for this package.
This deal is very unlikely and the Heat probably say no, but it is an interesting hypothetical give the all three franchise's current needs.
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Jackson Caudell has been covering Georgia Tech Athletics For On SI since March 2022 and the Atlanta Hawks for On SI since October 2023. Jackson is also the co-host of the Bleav in Georgia Tech podcast and he loves to bring thoughtful analysis and comprehensive coverage to everything that he does. Find him on X @jacksoncaudell
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