If The Red Sox Don’t Extend Garrett Crochet, Then Trading For Him Was A Big Picture Mistake

Let’s take a look at the stat lines of a couple of left-handed pitchers over the last five years. Each has been traded in the last 13 months:

In addition to both of these guys being exceptional when on mound and not being able to toe the rubber very often, they both have two years of team control left before they can make the decision to test free agency.

One of them was traded by the Red Sox in exchange for Vaughn Grissom; the other was traded to the Red Sox in exchange for Kyle Teel, Braden Montgomery, Chase Meidroth and Wikelman Gonzalez.

Yes, we’re talking about Chris Sale and Garrett Crochet.

Now, the point of this exercise isn’t to tell you that Crochet is Chris Sale, because he’s not. Once you get beyond the things listed above and the White Sox to Red Sox connection, there’s some pretty massive differences including age, body type, and the brand of injury setbacks. But what I am concerned about when it comes to this exercise is the matching number of years of team control left for each player, because that has the potential to destroy just about everything that makes Crochet the more valuable long-term, championship building block.

Crochet avoided arbitration on Thursday, agreeing to a one year, $3.8 million dollar deal. He will be arbitration eligible one more time in 2026 before possibly becoming a free agent at the end of that season.

Sale, meanwhile, has one year left on his deal at $22 million, but then there’s a team option for $18 million in 2026, which will undoubtedly get picked up if 2025 goes anything like his 2024 campaign.

In other words, without any big moves, there’s a decent chance both Crochet and Sale hit free agency at the same time a little less than two years from now. And if that happens, the Red Sox have grossly mismanaged the situation.

Regardless of where you fall on Sale, he represents a short-term rotation wild card piece with an extremely high boom or bust potential. Just last year he was both the Cy Young winner and a guy who couldn’t go when the Braves needed him most in the Wild Card round against the Padres (where the two starting pitchers they did use in that series went a COMBINED 3.1 innings pitched, giving up 8 runs).

In the short-term, both Crochet and Sale are high ceiling-enigmas, with carrying almost the same Cy Young odds for the 2025 season (Crochet +700 and Sale +800). What makes Crochet unique, and ultimately so much more expensive in a trade, is his long-term high-ceiling and the possibility to lock him down through that window before he proves he can put it all together. They are one extension away from possibly getting him at an incredible value.

However, if the Sox don’t land the extension half of the parley, many of the best aspects of the trade go away. The long-term upside value will be lost. Without an extension, it doesn’t matter that Crochet’s just 25 right now. He could be pitching in another uniform at 27.

Photo by Maddie Malhotra/Boston Red Sox/Getty Images

We can look at this from another perspective. In trading Kyle Teel, Braden Montgomery, Chase Meidroth and Wikelman Gonzalez, the Red Sox gave up what could potentially amount to 24 years team control (6 years for each player if they all make and stay in the majors, and that’s before you even consider that the overall number could be closer to 28 years total if the White Sox manipulate their service clocks). For this haul, the Red Sox got back a guy in Crochet who is only under control for two more years, but might be willing to double, triple, or quadruple that figure depending on the extension offer.

That’s an incredibly bold move by Craig Breslow and company! It’s the kind of move the Sox haven’t made in years, and it’s even bolder when you consider Crochet’s pitched in a grand total of 12 big league games in which he’s thrown more than five innings. (The context there being the White Sox used him as a reliever when he first came up and then he went for Tommy John surgery.)

To their credit, the front office saw a guy they think has ace potential, and moved an enormous amount of prospect capital to land him. But here’s the thing: If you believe in Crochet enough to part with those prospects, then you also need to believe in Crochet enough to pay him a large extension. You’re going to get a discount on what an ace would cost on the free agent market, but you’re still going to have to pay. Simply put, if you’re willing to give up what it takes to trade for Boardwalk, then you also need to be willing to pay what it takes to put hotels on it. The overall strategy just doesn’t work in the grand scheme of things unless you complete the second leg of the process.

It’s one thing if you don’t want to pay to put hotels on the green monopoly, or in this case pay the price for free agent pitching like Blake Snell, Corbin Burnes and Max Fried (all between the age of 30 and 32). But if you’re not willing to pay for Crochet in 2027 and beyond after you made it clear you believe in him enough to move 4 of your top 15 prospects in your system, then what the hell are you doing?

It’s hard to fully gauge the Crochet acquisition right now because I still view it as incomplete without the extension. If they get that piece done and everything breaks right, they might end up with a younger, better, and cheaper ace stretched across the same timeline where Roman Anthony, Kristian Campbell, and Marcelo Mayer are all under team control. That would be an incredible maneuver by the Sox!

And who knows, they might even be smart by waiting deeper into the offseason to get this done as so much of the MLB books are now about the AAV of a contract and how it relates to the luxury tax (oddly, also the spot on the Monopoly board next to Boardwalk). Perhaps the Sox can play more games with the AAV numbers after they know where a couple of other offseason moves land them and pinpoint exactly how to massage things to get the final tally they need. Riveting stuff, I know, but unfortunately it matters.

Given the recent run of disgraceful seasons from this franchise though, they don’t deserve the benefit of the doubt on that. Not until an extension is on the books. What we know for now is a deal is not done, Opening Day is less than three months away, and Crochet’s price tag could skyrocket if he makes even a handful of starts and pitches well. The window exists now, and it’s likely going to close shortly.

We’ve reached the point in the game where the Red Sox have to spend some serious long-term money to tie it all together, and so far, they still haven’t been willing to do that. We’re not quite down to the buzzer yet, but the clock sure is ticking. Get it done!