Ira Winderman: Comparative analysis creates cold-cash realities for Heat, Tyler Herro

Ira Winderman, South Florida Sun Sentinel on Aug 10, 2025

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MIAMI — Unlike Jimmy Butler a year ago, when July meant go time with his extension window, there is considerably more breathing room for the Miami Heat this offseason when it comes to Tyler Herro, whose extension window does not open until Oct. 1 (and closes on Oct. 20).

On one hand, that allows for comparative analysis.

On the other hand, that allows for comparative analysis.

To wit:

Over the past week, New York Knicks guard Mikal Bridges agreed to a four-year, $150 million extension. The simple math: $37.5 million annual average.

Also this past week, San Antonio Spurs guard De’Aaron Fox agreed to a four-year, $229 million extension. That math: $57.3 million annual average.

For his part, Herro on Oct. 1, the three-year anniversary of his previous extension, becomes eligible for a maximum three-year, $149.7 million extension. That math: $49.9 million annual average.

There assuredly are plenty of ways to parse those three sets of numbers.

Bridges, who turns 29 later this month, has never been an All-Star or All-NBA selection, and has been to one NBA Finals (2021) since being drafted in 2018.

Fox, who turns 28 in December, was an All-Star in 2023 and third-team All-NBA that year, with his lone playoff appearance ending in the first round (2023) since being drafted in 2017.

Herro, who turns 26 in January, was an All-Star this past season, has never been All-NBA and was on teams that twice advanced to the NBA Finals (2020, playing a major role; 2023, injured) since being drafted in 2019.

Of those three, Herro is the only one to have won a major NBA award, named Sixth Man of the Year in 2022 (Bridges made first-team All-Defensive in 2022).

So is Herro closer to Bridges’ salaries in an annual extension?

Closer to Fox’s payday?

Or somewhere in between?

To that end, a veteran NBA scout with decades of experience this past week was asked a simple question by the Sun Sentinel to anonymously rank (since he is not at liberty to discuss players on other teams) Bridges, Fox and Herro as players, regardless of the amount of salary realized in extensions.

His response:

“1. Tyler Herro. 2. De’Aaron Fox. 3. Mikal Bridges. Bridges is clearly the third. Not quite the defender he’s cracked up to be. He is better in that area than the other two, but not enough to move him up. The other advantage he has is his durability. Herro is the best shooter, most efficient offensive player and has shown he can make plays. Fox has infrequently shot it well and is a poor defender, but is a productive scorer/playmaker. I think, after last year, Herro and Fox would be at least ‘No. 3s’ on contenders; a little less sure about Bridges. I always tend to favor the better offensive player.”

So — whoa — Herro up there in the Fox stratosphere?

“That,” the scout said of Fox’s extension, “was a big overpay, for sure.”

And that’s where comparative analysis tends to become more nuanced, because it often can be as much about a team’s situation as a player’s value.

For the Knicks, Bridges is asked to be nothing more than a fourth option, behind Jalen Brunson, Karl-Anthony Towns and OG Anunoby. Plus, this is New York’s locked-in, win-now roster, what they have been building toward for years.

For the Spurs, Fox can be extended an overpay while Victor Wembanyama, Dylan Harper and Stephon Castle are on rookie-scale deals, none of those three players are among the top five salaries for San Antonio.

But for the Heat, where the team stands when a Herro extension would kick in for 2027-28 remains an abstract. Beyond Bam Adebayo, nothing but great unknowns, with all due respect to the youthful potential of Kel’el Ware, Nikola Jovic, Kasparas Jakucionis, Jaime Jaquez Jr., etc.

In 2027-28, Adebayo will be earning $52.6 million on his locked-in extension. Would Herro and Adebayo, at a combined $100 million-plus be enough as leading men?

And then there is the element that stood so evident in the April record-setting playoff humiliation at the hands of the Cleveland Cavaliers — of Herro simply not being up to the defensive challenge at postseason moments of truth.

Say what you want about Bridges in the Knicks’ hierarchy, but he won’t be played off the floor on either end in the postseason.

In that regard, a Herro contract along the lines of Bridges deal would be reasonable considering the tradeoff of needed offense for defensive deficiency.

But something even close to what Fox received from the Spurs and it could feel like being locked into play-in purgatory.

Still, there is a risk in a waiting game on both sides. Without an extension in that three-week October window, Herro could return to the table for a four-year, $206.9 million extension next summer ($51.7 million average). Further, should he make one of the three All-NBA teams this coming season, he would then be eligible for a five-year, $380 million supermax contract ($76 million average!).

With Bridges and Fox, the week’s extensions opened eyes for comparative analysis.

For the Heat and Herro, that could prove eye-opening, with the potential need for dual compromise.