The Boston Red Sox could be on the verge of their biggest pitching gamble in years. Reports says they are preparing a five-year, $110 million extension for Garrett Crochet. He is a pitcher with elite power however, limited starting experience. This is not just a routine contract—it is a bet on upside over certainty. The approach could reshape Rox’s rotation. However, with the talent’s value rising, waiting could prove riskier. If the team needs him, now is the time. So, is this deal a valid approach or a gamble? One needs to break it down.

Alex Cora’s interest in Crochet is driven by talent and necessity. Drafted by the White Sox in 2020, he made a quick effect in relief before transitioning into a starting role. Despite missing 2022 because of Tommy John surgery, the 2024 Comeback Player of the Year award winner’s 2023 return highlighted flashes of dominance. By 2024, Crochet was an All-Star, with 209 strikeouts over 146 innings with a 3.58 ERA. Such numbers prove the power, however, Boston Red Sox’ situation makes this move more urgent.

The Rox are running out of options. Lucas Giolito’s hamstring injury and Brayan Bello’s delayed beginning have hit their rotation. Eying on Richard Fitts and Quinn Priester is not a winning equation for a team focusing on contend. In such a situation, Crochet fills a gap with high strikeouts, proven resilience and a enhancing ceiling.

That is why the team is acting now. The Boston is continuously offering a five-year, $110 million extension, focusing on to lock in a vital ace before his price skyrockets. This is a strategic approach. The Athletic’s Tim Britton backs this approach, saying that securing the talent now safeguards a future bidding war. The team is betting on power over past workload—however, is the risk valuable?

There is no guarantee the talent trusted as a full-time starter. In 2024, his strike out rate was 35.1 percent. This track record in relief is powerful, however, he has yet to prove durability over a full season. Still, the Boston Red Sox appears committed. Garret crochet himself has acknowledged the team’s interest, saying, “it is an honor to be considered a key part of Boston’s future. I am excited about the possibility of contributing to a championship-caliber team“. Such a mutual interest is visible, however, now the Boston needs to decide—do they go all in?

How The Boston Red Sox deal stacks up in the MLB market

If the Boston Red Sox hesitate, other teams could jump in. He has attracted the Mets, Yankees, Phillies, Orioles and Reds—teams thinking to add a frontline lefty to their rotation. If Crochet dominates in 2025, team, like, the Dodgers and Mets could escalate their pursuit. This will push his value larger. Look at Carlos Rodón’s free agency—injury risks did not stop him from landing a $162 million deal. This could happen with Crochet. After securing Max Fried, the Yankees could be out. However, the Mets remains aggressive suitor. The Boston Red Sox has the prospect capital to outbid others, however, will the team act before the market explodes?

Rox’s track record with pitcher extensions is not that good. The Chris Sale deal was $145 m for 5 years. It looked effective initially, however, injuries turned it into a nightmare. Before that, the Jon Lester contract saga saw the team lowball their ace, just to watch the star thrive elsewhere. The lesson? Timing is everything. If the front office commits to Crochet now, the team needs to structure the deal effectively—perhaps adding performance-based incentives. The power is there, however, history highlights that betting large on a young star is never without risk. Rox’s front office needs to get this one right.

The Red Sox face a pivotal decision—secure Crochet now at $110 million and risk losing him later. Such a move could stabilize their rotation. This can backfire too. What is your take? Does Boston need to lock in their future ace? Is this gamble too soon?