The Miami Heat and contract extensions are a tale of two opposite narratives. Of course, these narratives have precedence. Pat Riley has always been cautious with extensions, seeing how the rumors play out in the minds of the players as a window looms. As team president of the Miami Heat, he’s known for running a tight ship—respecting talent, but never letting anyone, no matter how big the name, operate above the culture he’s built. Doubts? Whether it’s LeBron, Dwyane Wade, or more recently, Jimmy Butler, Riley’s negotiation style is firm and unflinching. He’ll show respect, but not desperation. Recall the Jimmy Butler case, which led to one of the most storied player-team fallout in NBA history. For Bam Adebayo, it’s proved more fruitful than originally thought. So if you’re Miami, you’d be hoping Tyler Herro turns out to be the latter.

The Boy Wonder’s been a Heat boy since his inception in the NBA in 2018. And since then, season-by-season improvements have followed. But if you’re a Miami fan, you’ve seen this movie before. Jimmy Butler was their Jimmy Buckets. Since landing in South Beach in 2019, he’s been the fire in their veins, the walking definition of “Heat Culture.” From dropping 40-point triple-doubles in the 2020 Finals to carrying the 8-seed Heat on his back in 2023 like a man on a mission, Jimmy was making statements. But he didn’t see the end game coming this soon. No one expected him to down tools and protest against the club to let him go until it actually happened. If anything, Tyler has profited the most. And somehow, this was to be the most unexpected fact.

Back when they had their 10-game losing streak in March, Herro talked about his drop in performance after Butler’s exit. “I’m not getting any open looks… I’m pretty sure I shoot high 40s on open catch-and-shoot threes or open threes. I just haven’t gotten any good looks in the last about three months. … When Jimmy [Butler] was here, he created three to five threes for me per game, where he would drive and kick it to me. But we don’t really have anyone right now that’s doing that,” said Herro to the Miami Herald.

Little did he know that move would slowly morph him into a South Beach icon. He’s since become the spearhead in the Heat’s resurgence into a play-ins spot. And after a commanding victory against the Hawks, they now face a conference-topping Cavs beckon. But big moments call for big players, and Tyler Herro will be going into the daunting first-round playoff series with a point to prove- he’s not the “fragile” boy Pat Riley picked him out to be in the last off-season. Oh, and he also wrote a small history for Miami, after they became the first 10th-place team in either conference to make the playoffs through the play-in.

But two futures await the Boy Wonder for the coming season- he can either play the patience game or cash in for a smaller yet quicker pen-to-paper deal. Let’s break down the deals now, with insights from Ira Winderman’s reports to the Sun Sentinel.

Tyler Herro faces $207 million extension dilemma at Heat

Herro played just 42 games last season. And after an injury-riddled campaign, Heat president Pat Riley was the first to call him out on it. “He’s been fragile a little bit and broke his hand last year… and there isn’t anybody who works harder at his game…. But he’s got to make some adjustments.” Fast forward to this season, and he has flipped the script with 77 games so far. He’s since clapped back at the prez and showed his quality by taking the team’s offensive responsibilities in stride, averaging almost 24 points per game.

So two contract offers await him. “Based on Tyler’s current contract, he will be eligible for a three-year, $150 million extension that would start in 2027-28 at a salary of $46.2 million. So it comes down to whether the Heat view Tyler going forward as a $50 million player. But also appreciate that if Tyler opts to wait, he would be eligible to extend in the 2026 offseason for $207 million over four seasons, to be tacked onto the end of his current deal,” said Ira Winderman of the Sun Sentinel.

It’s all a game of patience. Herro’s extension window doesn’t open till October. So this gives Heat a chance to consider off-season transfers too. Shelling out a cool $200 mil isn’t an easy decision to make at all, so Miami will have to view all their potential options on the table to make sure that there’s maximum value-for-money in Herro’s case.

Tyler’s their second-best-paid player this season. And the latter contract extension will make Bam Adebayo topple for the top spot. So if you were in Tyler Herro’s shoes, what would you do? Cash in quickly to secure your future, or play the longer, riskier game and potentially profit more, later?