Inside the Garrett Crochet trade behind the 2026 White Sox
Chicago traded its ace to Boston in December 2024 for four prospects. Three of them are part of a playoff team, and an older Chris Sale deal supplied a fourth building block.
On December 11, 2024, the last day of baseball's Winter Meetings in Dallas, the White Sox traded the best pitcher they had. Garrett Crochet went to Boston. Four minor leaguers came back to a team that had just lost 121 games. I wanted to know what happened to all four, because the answer explains a surprising amount of the 2026 White Sox.
It was not even the first time these two clubs had made this kind of deal. MLB.com's Ian Browne opened his trade story by recalling that eight years earlier, also at the Winter Meetings, Boston had traded prospects to Chicago for another ace lefty, Chris Sale. Hold that thought. It comes back.
The four players Chicago received
| Player | Status at the trade | What happened by September 2026 |
|---|---|---|
| Chase Meidroth, infielder | Boston's No. 11 prospect | Everyday second baseman: .275/.350/.413, 16 HR, 4.4 WAR through Sept. 25 |
| Kyle Teel, catcher | No. 25 prospect in baseball, 14th overall pick in 2023 | 5 HR in 38 games around an injury rehab, plus a homer in the Sept. 24 clincher |
| Braden Montgomery, outfielder | No. 54 prospect in baseball, 12th overall pick in 2024 | Major league debut in 2026, then 6 HR in 91 games |
| Wikelman Gonzalez, pitcher | Boston's No. 14 prospect | 2.66 ERA in a 2025 debut, then designated for assignment August 8, 2026 |
The name that surprised me is Meidroth. Teel and Montgomery were the headliners, the two most recent first-round picks Boston had made. MLB Trade Rumors later observed that those two drew most of the headlines. By this September he had the second-highest Baseball-Reference WAR among White Sox position players, behind only Miguel Vargas, after playing 153 of the team's first 160 games.
Teel's year was interrupted by injury, and he returned from a rehab stint with Triple-A Charlotte on September 4. Twenty days later he homered to center field in the game that clinched the playoff berth. Braden Montgomery, the switch-hitter who once played at Stanford and Texas A&M, is still learning big-league pitching at 23. On September 4, the night of the team's wand giveaway, he and Colson Montgomery homered in the same game for the first time. Two Montgomerys in one lineup, both going deep on a giveaway night, is the sort of box score a rebuilding team dreams about.
Gonzalez is the one who did not stick. MLB Trade Rumors reported that he spent all of 2026 at Triple-A, missed about two months injured, and was designated for assignment on August 8 to open a roster spot for pitching prospect Hagen Smith. His 2025 debut, a 2.66 ERA in 20 1/3 relief innings, was genuinely promising. He was 24 when he was let go.
What Boston got, and why it was worth it to them
This was never a lopsided heist. In 2025 Crochet went 18-5 with a 2.59 ERA and led the majors with 255 strikeouts. He finished second in American League Cy Young voting and signed a six-year, $170 million extension. Red Sox chief baseball officer Craig Breslow said on the day of the deal that the club felt it had landed "a legitimate number one starter." For one full season, it had exactly that.
2026 went differently. Crochet made six starts with a 6.30 ERA, a number CBS Sports noted was badly skewed by one April 13 outing, then went on the injured list on April 29 with left shoulder inflammation. By September he was throwing bullpen sessions and talking about returning for the playoffs as a reliever, which is how he began his career in Chicago. He sounded entirely unbothered by the idea.
I'm not Joe Schmoe. I've done impressive things.
The Chris Sale echo
Here is the thought from earlier. When Chicago traded Sale to Boston on December 6, 2016, one of the prospects coming back was a hard-throwing right-hander named Michael Kopech. On July 29, 2024, the White Sox sent Kopech to the Dodgers in a three-team trade. Their return included Miguel Vargas, who hit 33 home runs for the 2026 club through September 25.
So two separate trades of an ace lefty to Boston, eight years apart, both feed this lineup. One route runs straight from Crochet to Meidroth, Teel and Braden Montgomery. The other runs from Sale to Kopech to Vargas. I did not expect the family tree to be that neat, and I checked it twice against the player records.
One more coincidence for the file. On the same December 11 as the Crochet trade, a pitcher named Mike Vasil was picked in the Rule 5 draft by the Phillies and flipped to Tampa Bay. Chicago claimed him off waivers the following March, and he is the dugout wizard of this season.
So who won the trade?
My honest answer is both clubs, and it is too early to score it properly. Boston bought an ace for a contending window and got a Cy Young runner-up season out of him before the shoulder trouble. Chicago turned one pitcher it could not afford to wait on into an everyday second baseman, a young catcher and a young outfielder, all of them 24 or younger this season. The White Sox clinched their first playoff berth since 2021 with all three on the roster, a climb told in full in our main story on the path from 121 losses to October.
What cannot be known yet is the part that decides these deals: what Teel and Braden Montgomery look like at 27, and whether Crochet's shoulder lets him be the pitcher he was in 2025. Check back in three years. For now, a rebuilding team sold its best player and got a big piece of a playoff roster back, which is how rebuilds are supposed to work and so rarely do.
Sources
Every factual claim above traces to one of these. Links open in a new tab.
- Red Sox acquire left-handed pitcher Garrett Crochet from Chicago White Sox
- Crochet dealt to Red Sox for big prospect haul
- 2026 Chicago White Sox Batting Statistics
- Garrett Crochet Stats
- White Sox Designate Wikelman Gonzalez For Assignment
- Garrett Crochet's return to the Red Sox could come with a twist: 'I'm not Joe Schmoe'
- Red Sox put ace Crochet on IL with shoulder inflammation, recall Eaton
- Michael Kopech
- Braden Montgomery
- Vasil is magical for White Sox despite not playing this season
