Breaking Down the Red Sox-White Sox Winter Meetings Blockbuster

It’s no secret that the Boston Red Sox have long been interested in Chicago White Sox pitcher Garrett Crochet. Days before the trade deadline back in July, Ken Rosenthal reported that Boston had shown varying levels of interest in the left-hander. Any trade for one of the top arms in baseball will surely cost a number of prospects and/or proven MLB talent, and a move for Crochet was always going to fetch the White Sox a hefty return. Considering the state of the organization, holding onto Crochet didn’t make much sense or fit their competitive window.

On the other hand, the Boston Red Sox have been looking for elite pitching. With an arsenal full of very good mid-rotation starters but lacking true top-of-the-rotation arms, President of Baseball Operations Craig Breslow and Manager Alex Cora have been vocal about acquiring high-level pitchers. At around 2:00 p.m. on day three of the Winter Meetings in Dallas, the baseball world was treated to the first blockbuster of the offseason.

BREAKING: The Boston Red Sox are finalizing a trade to acquire left-hander Garrett Crochet from the Chicago White Sox, sources tell ESPN. The deal is in the medical phase. Not official, but trending toward it.

— Jeff Passan (@JeffPassan) December 11, 2024

Garrett Crochet was heading to Boston in return for prospects Kyle Teel, Braden Montgomery, Chase Meidroth, and Wikelman Gonzalez. For many fans in Boston and Chicago, this deal probably felt like déjà vu. No one could forget the trade struck between the two almost eight years ago to the day, famously sending Chris Sale to Boston for prospects Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz. At the time, Moncada and Kopech were the Red Sox’s No. 1 and 5 prospects on MLB Pipeline, respectively.

Now, eight years later, we have an eerily similar deal. Garrett Crochet may not have the statistical accolades that Chris Sale had at the time of the trade, but he certainly has the potential to achieve them. Through the first half of 2024, Crochet had consistently been one of the best pitchers in baseball. Despite being placed on an innings limit after the All-Star break and not having the same numbers, he posted a 13.7 K/9 in the second half. Among pitchers with 100+ IP in the regular season, he led the league with a 12.9 K/9. He ended the year with a 3.58 ERA and a 2.69 FIP.

Perhaps more importantly than his numbers, Crochet represents the Red Sox’s desire to win now. After constructing what was regarded as one of the top farm systems in baseball, they cashed in some of those prospects for one of the most promising young arms in the game. After missing out on Blake Snell, Max Fried, and likely passing on Corbin Burnes, they needed to explore adding their potential ace via trade. Sure enough, after seemingly being far apart in trade talks, the two teams came together to get a deal done. The Red Sox got a guy they’ve been eyeing for a while with a good chance to ink an extension, and the White Sox received a massive prospect haul.

White Sox acquiring Garrett Crochet from Red Sox for catcher Kyle Teel, outfielder Braden Montgomery, infielder Chase Meidroth and right-hander Wikelman Gonzalez, sources tell @TheAthletic. First: @byJulianMack

— Ken Rosenthal (@Ken_Rosenthal) December 11, 2024

Make no mistake about it: the Red Sox gave up a ton in this deal. The White Sox did very well, getting back multiple top-100 prospects. “We were focused on bringing in as much high-end talent as we could,” White Sox General Manager Chris Getz said after the trade. In return for Crochet, they landed Boston’s last two first-round picks in Teel and Montgomery.

The initial reaction to the trade was chaotic. It was first reported that Teel would be involved, which alone was a surprise, as he was part of Boston’s “big four.” But it wasn’t until the rest of the package was revealed that the true magnitude of the trade became clear. After seeing Montgomery, Meidroth, and Gonzalez named in the deal, it’s fair to say it was pretty shocking. That’s about as steep of a return as the Red Sox could offer without moving their top three prospects: Roman Anthony, Kristian Campbell, and Marcelo Mayer.

To fully grasp the extent of the deal, you need to evaluate the talent the White Sox are receiving in return for Crochet. Most of Kyle Teel’s value stems from his catching, but he demonstrates unbelievable discipline and determination to play at a high level and contribute to winning. Teel somewhat struggled after his late-season promotion to Triple-A Worcester but ended 2024 with an .819 OPS. Behind the plate, he’s more athletic than most catchers but experienced ups and downs defensively. Series to series, the defense looked very different. If his receiving skills take a step forward, he’ll have a spot in MLB soon.

Braden Montgomery likely has the potential to be the best prospect in this trade. Although he hasn’t played a single professional game due to an ankle injury during the College World Series, he possesses multiple plus tools. Featuring a huge arm paired with tremendous power, Montgomery has future All-Star written all over him. It came as a surprise that he even fell to the Red Sox at No. 12 in the draft last July. There are swing-and-miss concerns—he struck out 25% of the time in his final year at Texas A&M—but he still profiles as a really gifted hitter. It probably took parting with Montgomery to make this deal possible for Boston.

Chase Meidroth is an all-around professional hitter. In 122 games in Triple-A last year, he posted a 132 wRC+ and an .838 OPS. He plays solid defense, gets on base, and doesn’t strike out much. Although he impressed over the last few seasons, there wasn’t a realistic path for Meidroth to be anything more than a reserve with the Red Sox. They already face a logjam of infielders, so a trade to Chicago could be really good for him. He should get time on the big league roster as soon as this season.

The legend of Wikelman Gonzalez is over in the Red Sox organization. In 2023, he was heralded as the Red Sox’s top pitching prospect. The Sox even added him to their 40-man roster to protect him in the Rule 5 draft in November 2023, after not doing so the year prior. When his fastball is working, it’s fantastic. He throws hard and pairs it with a curveball with huge drop. However, following two years where he struggled with control, his future was uncertain. With Chicago, he may get the chance to start again, whereas Boston was experimenting with him in the bullpen. Gonzalez still very much has the ability to recoup some of his former dominance and re-establish himself.

The term “overpay” has been thrown around with this trade, but in reality, that may not be fair to either side. For the White Sox to move Crochet, they were always going to demand a package of this stature. The cost of elite starting pitching in today’s market commands at least one top-100 prospect, and in this case, two. On the other hand, the Red Sox needed pitching. They needed someone who could change the complexion of their rotation, and that’s what they got in Crochet. “We weren’t going to leave Dallas without an elite starter,” Alex Cora said. “That was our goal.”

With their loaded farm system, this deal also made sense for Boston for the simple fact that they could afford it. They were one of a few teams that could move players like Teel and Montgomery without sacrificing their future since they still have Anthony, Campbell, and Mayer. It was the right time to utilize their system that had been marinating for the last few years and acquire one of the game’s best pitchers.

Both Boston and Chicago walk away from this deal in a better place. Although the Red Sox lost four of their top 12 prospects, they now have an ace. Although the White Sox lost one of their best homegrown talents of the last decade—including a jump straight to the majors after being drafted, they bolstered their farm system in a big way. The main takeaway is centered around the return—you need to give something to get something.

With Chicago building for the future, they say goodbye to Garrett Crochet. Boston yields a huge return but proves their intentions to be aggressive and compete now. The contrasting directions made this blockbuster right for both teams, and the careers of the five involved will be something to watch for years to come.