Red Sox Acquire Garrett Crochet in Winter Meetings Blockbuster

“Hey, they won’t have to say ‘we tried’ this time.” I can’t attribute that quote to anyone in particular, but the Winter Meetings were abuzz with variations on a theme. After missing out on Juan Soto and Max Fried earlier in the week, the Boston Red Sox switched gears from free agency to the trade market and found their star. In a blockbuster deal, they’re acquiring Garrett Crochet from the Chicago White Sox in exchange for Kyle Teel, Braden Montgomery, Chase Meidroth, and Wikelman Gonzalez, as Julian McWilliams of the Boston Globe first reported.

This is the biggest trade of the offseason, and it’ll almost surely still occupy that position when next season rolls around. Pitchers like Crochet don’t hit the market very often. He blew the doors off the league in his first year of starting, pairing premium velocity with two excellent secondaries. He threw 146 innings, struck out more than 200 batters, and barely walked anyone while doing so. His strikeout stuff, exploding fastball, and lanky lefty frame call to mind Chris Sale, another Sox-to-Sox trade piece, and with the White Sox in the middle of a gut-renovation rebuild, he was always likely to get traded. The only questions were who for, and which team was most interested in adding him to their rotation.

We’ll cover the ins and outs of the prospects included in the deal in a separate post. Broadly speaking, though, the White Sox got a little bit of everything in their return. Teel is a Top 100 catching prospect approaching major league readiness with impressive speed. Montgomery is a high-risk, high-reward outfield prospect, the 12th pick of the 2024 draft. Gonzalez has mouth watering stuff that took a step back this year, and a sky-high walk rate to match. Meidroth is an on-base genius with questionable power and an uncertain defensive future. The White Sox have so many needs that they don’t have to be choosy about filling particular holes or looking for particular profiles. They just need talent. This return fits well with that best player available mentality.

It’s a different story in Boston. The Red Sox rotation was better than expected in 2024, but it wore down meaningfully throughout the year. Their much-documented new approach – fewer fastballs and more secondaries, basically – coaxed several better-than-expected seasons out of their existing starters, but the league seemed to catch up to the new plan in the second half. Between that regression, some injuries, and Nick Pivetta’s departure in free agency, the Sox didn’t have sufficient horsepower to go toe-to-toe with the best of the AL East.

Crochet changes that. He has best-pitcher-in-baseball upside. He has a late-inning reliever’s fastball, a hard cutter reminiscent of seeing Jacob deGrom’s slider in a mirror, and a nasty sweeping slider that seems to take a sharp right turn just in front of the plate. When he’s cooking, Crochet can slice a lineup apart effortlessly. When teams talk about wanting to build a playoff-ready rotation, Crochet is basically what they’re imagining in the no. 1 spot.

Does he come with some risk? Well, yeah. He hadn’t started a game in the pros before 2024, and the White Sox accordingly treated him with kid gloves in the second half. He didn’t throw a single pitch in the fifth inning after June 30. I would have done the same thing if I were them, to be clear – even in college, Crochet never topped 65 innings in a season, so this year’s 146 was a career high by a mile even with the throttled-down second half. But there’s plenty of uncertainty around his workload, and that’s nothing new.

Crochet went straight from the draft to the majors, and only partially because of the cancelation of the 2020 minor league season. He mixed starting and relieving at the University of Tennessee, and the 2020 White Sox were looking to fortify their pitching staff for the playoffs, so they prioritized getting something out of Crochet right away rather than building him up as a starter. He was so immediately electric that they stuck with that plan in 2021, and he was dominant again. Then he tore his UCL before the 2022 season and missed most of the next two years recovering.

That unique usage history – he’d thrown only 85.1 innings as a professional before last season – makes for some huge error bars around his projected future. He’s been a traditional starter for three months in the past five years, but he was the best pitcher in baseball for those three months, racking up 3.7 WAR in 101.1 innings. Extrapolate that out to a 180-inning workload, even with a little bit of run-prevention regression baked in, and he’s a perennial Cy Young contender. But as my high school statistics teacher taught me, forecasting out of sample is risky business, and we just don’t know how Crochet’s body will hold up to the rigors of those 180 innings.

The Red Sox will do everything they can to limit that risk. They’ll find him extra rest days, sometimes through the use of a six-man rotation and sometimes merely by using off days to space out his starts. Unlike their Sox counterparts in Chicago, they’re hoping to use Crochet in October, too, so starting slow and building up seems like the best path forward. You can look at late-career Sale, Tyler Glasnow, and maybe Cy Young-era Corbin Burnes for workload analogs. Major league teams haven’t solved pitching injuries by any stretch of the imagination, but they’re good at getting important innings out of dominant starters, even when the starters can’t produce gargantuan innings totals.

This trade makes the Red Sox better in 2025, and that’s just the beginning. Crochet is under team control for two years, and it would behoove Boston to get the extension gears turning immediately. Crochet notably told teams he wouldn’t pitch in the 2024 playoffs (if traded — the White Sox were never close to playoff contention) without a contract extension, a reasonable request given his ballooning workload and the win-today mindset the playoffs bring out.

But that’s not why I’d be looking to extend him if I were Boston. Presumably, we’ll have a lot more information about Crochet’s long-term prospects by the end of this season, but it’s hardly a given that things will go swimmingly. He could get hurt. He could lose velocity or stuff as he builds up his innings count. But things could go the other way, too. Maybe he’ll continue to hone his command and develop a better offspeed pitch. The range of outcomes here is enormous, which means his future earnings have huge variance too.

Thanks to his surgery-related absence, Crochet made nearly the league minimum in his first year of arbitration ($800,000). He’s projected to earn $2.9 million in arbitration this year thanks to the path-dependent nature of the system. That will put his career earnings around $10 million, with roughly half of that coming from his draft signing bonus. That’s a notably low amount for a Cy Young candidate rapidly heading towards free agency. Signing an extension that sets him up for life financially is clearly important to him, and this winter feels like the best time for him to do it.

It’s also the best time for Boston to engage in these talks. Teams are better positioned to take on that kind of risk. To simplify, let’s say that Crochet is either going to make $10 million or $250 million from 2026 through 2032, earnings that reflect a range of outcomes spanning from injuries that persist for an unfairly long time all the way to a big contract in free agency. Let’s further say that the good outcome is 75% likely for the sake of some back-of-the-envelope math. Crochet’s expected earnings are $190 million, but 25% of the time, he makes way less than that. The Sox could offer him, say, $160 million for those seven years and make everyone happy (the total deal would then be eight years and $163 million, accounting for this year’s arbitration estimate). They get a discount to expected value. Crochet essentially gets insurance – no matter what happens, he ends up with lifetime earnings over $100 million, generational wealth. Everyone wins.

The math won’t work out this way next winter. By then, there will be much less uncertainty. An extension won’t make as much sense for anyone, no matter the outcome. If Crochet is great, he’ll be less interested in insurance. If he’s bad or gets hurt, it’ll be too late to hedge. This is the first time in his life that Crochet has the chance to get a career-making contract. It’s also the best time.

Boston has similar incentives to get a deal done this winter. There’s a reasonable chance that Crochet ends up as the kind of starting pitcher who sets salary records. He’s going to reach free agency before his age-28 season, and if he’s healthy for the next two years, he could easily be the best pitcher in baseball when he hits the market. That’s the kind of résumé that gets teams starry-eyed, the kind that comes with contracts the Red Sox have historically eschewed. By signing him to an extension now, they can avoid that possible disaster.

The downside risk is far more manageable for a team with Boston’s resources. The team has run payrolls in the $180 million to $250 million range for years, and would have no problem fitting a contract with an average annual value around $20 million into that. In the worst case scenario, that’s no fun for anyone, but $20 million in dead money wouldn’t prevent the Red Sox from contending by any stretch of the imagination.

I asked Dan Szymborski for a ZiPS projection of the next seven years to get a sense of the central case for Crochet’s contract. The model is skeptical of his innings loads but is quite optimistic about his talent level. It thinks that Crochet will average more than three wins a year without ever building up to more than five innings a start:

Signing a guy who might be a generational pitcher to a contract extension is a great reason to trade for Crochet. Even better, the Red Sox didn’t have to deal any of their three buzziest prospects (Roman Anthony, Marcelo Mayer, and Kristian Campbell) to do it. This trade makes good use of their excellent farm system; when you have so many prospects that it’s tough to find playing time for all of them, consolidating all that potential value into a star is an excellent decision. This isn’t trading from the offense to improve your pitching; it’s going to be a huge net improvement for the club in the next two years, even ignoring a potential extension.

That doesn’t mean I dislike Chicago’s side of the deal, though. For comparison, consider this spring’s Dylan Cease trade. Both were four-player deals headlined by a top 100 prospect. Both sent away pitchers with two years of team control and tantalizing upside. I like Teal more than Drew Thorpe, the gem of the Cease return, and Montgomery is a great risk-reward play.

While the Red Sox didn’t have anywhere to play these fascinating prospects, the White Sox have opportunities for days. They’re trying to rebuild an entire roster from the ground up, and I like that they’re prioritizing depth in doing so. They should be leaning into volatility wherever possible, and not only did they get a bunch of prospects, they got guys with big error bars around their future value. I think that’s an excellent decision.

Does this deal change the balance of power in the AL East? I’m not sure. The Yankees and Blue Jays have both upgraded this week, and I expect both of them to make more moves too. The Orioles have a new owner and young players coming out their ears; they could be movers and shakers in the next month and they’ve averaged 96 wins over the past two years. The Rays are always in the mix. This trade doesn’t guarantee anything for Boston, and if they don’t do anything to improve their offense, they might struggle to score enough to make a run at the division title. But that doesn’t change the fact that this move makes them a lot better, and it even leaves them with the financial flexibility to make further improvements. I think that both teams did very well on this deal; Boston was a natural fit for Crochet, and the White Sox targeted the exact kind of return I’d be looking for in their shoes. Great work by everyone – now let’s get a contract extension done.

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