Analysis: Garrett Crochet extension is huge gamble that Red Sox had to make

What a difference a few days makes.

Last week Garrett Crochet and Red Sox officials were publicly throwing in the towel on extension talks. The left-hander had set an Opening Day deadline for any deal, and when Thursday came and went with no agreement it seemed as though a new contract would have to wait until the winter.

Now? Crochet and the Red Sox will be together through the rest of the decade and beyond.

Monday night Crochet and the Red Sox reached an agreement on a new six-year, $170 million contract extension that will run from 2026-31 and includes an opt out after 2030. The deal is the second largest contract in Red Sox history for a pitcher behind only David Price’s seven-year, $217 million deal signed prior to 2016, and it is the largest in MLB history for a pitcher with four years of service time.

It is also a huge gamble for the Red Sox, but one the club had to make.

The Red Sox paid a substantial price to land Crochet in the first place, trading away four prospects to the Chicago White Sox, including top-100 prospects Kyle Teel and Braden Montgomery. Crochet is regarded as one of the top young pitchers in baseball, but with only two years of team control remaining failing to lock him up for the long haul would have been a massive organizational failure.

Prior to the deal a worst-case scenario might have seen Crochet sign with another team in free agency two years from now while Teel and Montgomery each emerged as stars with the White Sox. Now the Red Sox can at least count on having Crochet through his prime years.

Still, the extension presents some risk.

For all of his talent, Crochet’s track record is relatively short. He has only pitched one full season as a starting pitcher, and since making his MLB debut in 2020 he’s logged just 224 innings total. There is no guarantee he will continue to pitch at an elite level, and even if he does there is always a possibility he could get hurt.

Even knowing all of that, the Red Sox have good reason to believe Crochet will be worth the money and then some.

Last year Crochet struck out 209 batters in 146 innings, and he could have thrown even more had the White Sox not limited him to around four innings per start throughout the second half to protect him from overuse after he nearly doubled his career-high in innings thrown by the All-Star break. His advanced metrics are off the charts as well, and entering the season he was among the betting favorites to win the AL Cy Young Award.

Most importantly, Crochet is only 25 years old. Most elite pitchers don’t hit the open market until their late 20s or early 30s, and when they do they often command huge dollars despite being near the point where history suggests a decline should be imminent.

Crochet will be a bargain by comparison at less than $30 million a year on average, and he should just be getting started.

The initial trade to land Crochet this past December was the first concrete indicator that the Red Sox were actually serious about competing after years of empty words. Deals with Walker Buehler and Alex Bregman in free agency followed, and now by extending their new ace the Red Sox have put the finishing touches on a potentially transformative offseason.

History will ultimately judge this deal by how Crochet performs in the future, but at this moment in time it’s hard to see the extension as anything other than a massive win. The Red Sox no longer have to worry about going into next season with Crochet’s pending free agency looming over the franchise, and had the two sides tabled negotiations until next winter there’s a good chance Crochet could have raised his price tag significantly in the meantime.

Best of all, the Red Sox have ensured that Crochet will remain atop the club’s rotation throughout what they hope will be a long period of sustained championship contention. Any team that aspires to play deep into October needs a No. 1 guy, and now the Red Sox have theirs.

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