Former Boston Red Sox first-round pick Braden Montgomery made his major league debut on Tuesday night for the Chicago White Sox. With Montgomery’s debut, all four of the pieces Boston sent to Chicago in the December 2024 blockbuster for ace Garrett Crochet have become big leaguers. Was it all worth it? 

Let's dive in.

After months of speculation, newly hired Chief Baseball Officer Craig Breslow made the first big splash of his tenure, landing 24-year-old ace Garrett Crochet from the White Sox in exchange for 2024 first-round pick Montgomery (No. 5 in Red Sox organization), catcher Kyle Teel (No. 4), infielder Chase Meidroth (No. 8), and pitcher Wikelman Gonzalez (No. 18). 

In landing Crochet, Boston acquired the ace that had evaded them since Chris Sale’s 2018 season. The then-24-year-old was coming off a breakout campaign on the South Side, posting a 3.58 ERA and striking out 209 batters across 146 innings, with his workload monitored down the stretch. Shortly after arriving, the budding star agreed to a six-year, $170-million contract extension, tying the lefty to Boston through at least the 2030 season.

Crochet immediately established himself as one of the best arms in baseball, posting a 2.59 ERA in a career-high 205.1 innings, leading the league in strikeouts with 255 en route to a second-place finish in the American League Cy Young Award voting. 

Crochet got off to a rough start to the 2026 season, posting a 6.30 ERA in 30 innings. He has been on the injured list since April 29 with left shoulder inflammation. And things appear even worse now than they did at the beginning of the injury.

After a draft day slide, the Red Sox selected the left-handed hitting catcher with the 14th overall pick in the 2023 MLB Draft. Teel spent the first two years of his professional career in Boston as a member of the original 'big three' with fellow top prospects Roman Anthony and Marcelo Mayer. 

In 138 games in the Boston organization, Teel hit .301/.404/.444/.844, though questions about his defensive development led to doubts about whether or not he could stick behind the plate. 

The 23-year-old catcher made his major league debut for Chicago in June 2025, hitting .273/.375/.411/.786 in 78 games for Chicago. However, the defensive metrics were less kind to Teel, as he ranked in the fifth percentile for blocks above average and in the 24th percentile for caught steals above average. 

Teel has missed the White Sox' first 67 games of the 2026 season with a sprained LCL in his right knee. 

After sliding in the draft thanks to a broken ankle suffered during the College World Series, Montgomery was selected by the Red Sox with the 12th overall pick out of Texas A&M.   

Montgomery wouldn’t make his professional debut until 2025 with Chicago’s Single-A affiliate. The 23-year-old switch-hitting outfielder tore through the minors in only 775 plate appearances, hitting .284/.381/.477/.858. 

He made his major league debut on Tuesday night in Chicago’s 6-5 win over the Braves, where he went 2-for-5, becoming the fifth player in major league history to hit a walkoff home run in their debut. 

Seen as a hit-first prospect, Meidroth was a bit of a forgotten man in a Red Sox system that was, at the time, loaded with exciting young players. The right-handed hitting second baseman was incredibly productive in 122 games with Triple-A Worcester in 2024, hitting .293/.437/.400/.837 before being dealt to Chicago. 

After just nine games in Triple-A Charlotte, Chicago promoted Meidroth to their major league roster, where he has hit .260/.334/.344/.678 across 187 games. He is currently on a 21-game on-base streak. 

The 24-year-old right-hander was the lowest-rated prospect included in the deal for Crochet. Gonzalez signed with Boston for $250,000 out of Venezuela as a part of the 2018 international free agent class. 

Gonzalez made 24 appearances (19 starts) for Double-A Portland in his last season in the Red Sox organization, where he posted a 4.73 ERA in 84.1 innings pitched. After 26 appearances, mostly all in relief in the White Sox organization, Gonzalez made his major league debut on June 20, 2025. He appeared in 16 games for Chicago, with a 2.66 ERA in 20.1 innings of work. 

The 24-year-old has made 11 appearances for Triple-A Charlotte in 2026 where he has posted a 2.57 ERA in 14.1 innings. 

Not every deal has to have a clear winner and loser, and this deal between the two Sox is a clear win-win, with both sides getting exactly what they were looking for. 

Boston was able to supplement its incredible core of position-player prospects with the young, controllable ace it had been seeking for years, without costing it Mayer or Anthony.

The White Sox were able to jump-start their rebuild with at least three pieces who tore through the minors and became centerpieces of their new core, which has them in first place in the American League Central for the first time since the end of the 2021 season. 

The Red Sox sit at 27-29, 12 games under .500 for the first time since the 2020 season. They are off on Thursday before welcoming the Texas Rangers to Fenway Park for a three-game weekend series that begins Friday night. Sonny Gray (7-1, 3.20 ERA) opposite Jack Leiter (3-5, 4.69 ERA) for Texas. First pitch set for 7:10 p.m. ET. on Friday night. 

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