Southpaw pitcher Garrett Crochet had a remarkable 2024 campaign for a struggling Chicago White Sox team. The No. 11 overall pick in the 2020 draft underwent Tommy John surgery in April 2022, resulting in his absence for the entire season and a significant portion of the following year. Due to a combination of the pandemic, his lengthy recovery, and being utilized solely in a relief role at the Major League Baseball (MLB) level, Crochet accumulated a total of just 88.2 innings pitched across all levels from 2020 to 2023. Consequently, the White Sox adopted a cautious approach with him during the latter half of the season, with his last appearance extending into the fifth inning occurring on June 30. Despite these challenges, Crochet emerged as one of the most valuable pitchers in baseball, as indicated by FanGraphs, leading to speculation about his potential as a trade asset as the trade deadline approached. However, the White Sox ultimately opted not to trade him, raising questions about whether this offseason will mirror the previous one when they dealt away ace-caliber pitcher Dylan Cease, who was traded to San Diego with two years of arbitration eligibility remaining before becoming a free agent. In that move, the White Sox received veteran reliever Steven Wilson along with three of the Padres' top ten prospects, though none were ranked among the top 75 overall at the time of the trade. Given Crochet's strong season, the White Sox are likely seeking a more significant return compared to what they received for Cease, particularly since Crochet's projected salary for the upcoming season is anticipated to be $2.9 million, notably lower than Cease's $8 million for 2024. It is expected that more than half of the 30 MLB teams would be interested in acquiring Crochet for the next two seasons, prompting an analysis of several hypothetical trade packages.

One potential trade scenario involves the Baltimore Orioles, who would send catcher/first baseman Samuel Basallo and right-handed pitcher Alex Pham to the White Sox in exchange for Garrett Crochet. The Orioles are viewed as contenders thanks to their plethora of coveted prospects and a pressing need for starting pitching. Even after acquiring Zach Eflin and Trevor Rogers, both of whom are under team control until at least 2025, Baltimore remains a leading candidate to pursue Crochet this offseason. However, the depth of the Orioles' farm system has diminished compared to the previous year due to trades involving DL Hall, Joey Ortiz, Connor Norby, and Kyle Stowers, in addition to the promotion of prospects Jackson Holliday and Heston Kjerstad to the majors. The Orioles still possess intriguing prospects in first baseman/third baseman Coby Mayo and catcher/first baseman Samuel Basallo, both of whom have the potential to be ranked among the top ten prospects overall in 2025. Making a deal could depend on their willingness to part with one of these young hitters to bolster their rotation, as trades involving lesser prospects may not suffice to secure Crochet.

Another hypothetical trade scenario positions the Boston Red Sox as a contender to acquire Crochet. Boston could offer outfielder Roman Anthony, shortstop Franklin Arias, and right-handed pitcher David Sandlin to the White Sox in exchange for Garrett Crochet and outfielder Luis Robert Jr. The Red Sox, while bolstered by the addition of Quinn Priester to their pitching rotation, have not been in a position spurring contention with their current arms. Improving the rotation should be Boston's primary focus this offseason, particularly given their struggles in total runs allowed. The Red Sox are equipped with six prospects ranked in MLB's top 100, including three in the top ten, all of whom are position players. This surplus allows Boston the flexibility to negotiate with Chicago, particularly if they can include Robert in the deal. The Red Sox are in need of both a potential ace and a right-handed power hitter, making Crochet an appealing target in their efforts to build a competitive roster.

The Chicago Cubs are also in the mix for a potential deal, sending outfielder Owen Caissie, shortstop Jefferson Rojas, and right-handed pitcher Brody McCullough to the White Sox for Garrett Crochet. Historically, the White Sox and Cubs have been known to engage in significant trades; past notable transactions include Jose Quintana being traded to the Cubs for Dylan Cease and Eloy Jiménez. Despite a lack of top-20 overall prospects, the Cubs possess eight players within MLB's top 100, which provides an opportunity for a deal. By bolstering their rotation with Crochet, the Cubs would elevate their competitive standing in the National League Central, especially if Crochet joins other solid arms like Shota Imanaga and Jameson Taillon.

The Cleveland Guardians, consistently challenged by budget constraints, could seek to acquire Crochet by offering outfielder Jaison Chourio, first baseman Ralphy Velazquez, and right-handed pitcher Braylon Doughty to the White Sox. The Guardians are interested in rebuilding their rotation and, given their historical tendencies to avoid large expenditures on free agents, may find trades to be their best option. Despite potential reluctance from the White Sox to strengthen a divisional rival, acquiring prospects from Cleveland could substantiate a long-term rebuilding strategy for Chicago, as they seek to develop key players for future seasons.

From the New York Mets' perspective, they could trade shortstop/outfielder Jett Williams, along with right-handed pitchers Nolan McLean and Jonah Tong for Garrett Crochet. The Mets are in need of pitching as they face the impending departure of several pitchers to free agency. Crochet might represent a cost-effective option as they rebuild their rotation. Williams, a 2022 first-round pick, has shown promising potential, although he may require a conducive opportunity to flourish based on the team's existing roster dynamics. Acquiring Crochet through this route would serve as a strategic acquisition, enabling the Mets to fill an immediate need in their pitching staff without committing to long-term contracts.

The Philadelphia Phillies are another team that has shown interest in acquiring Crochet. Previous reports indicated the potential for a deal involving Crochet, contingent upon the White Sox's willingness to negotiate without requiring top pitching prospect Andrew Painter in return. In a proposed trade, the Phillies could send shortstop Aidan Miller, catcher Eduardo Tait, and right-handed pitcher Seth Johnson to the White Sox for Crochet. Adding Crochet would provide the Phillies with a much-needed upgrade to their pitching staff while aligning with their financial strategies, considering his projected $2.9 million salary. Miller, being a highly regarded prospect, would provide a valuable asset for Chicago's rebuilding efforts.

Lastly, a potential trade could see the Pittsburgh Pirates sending right-handed pitcher Braxton Ashcraft, shortstop Mitch Jebb, and right-handed pitcher Levi Sterling to Chicago in exchange for Garrett Crochet. The Pirates, having fallen short of postseason contention in recent years, may be inclined to take significant steps to improve their roster by acquiring a standout pitcher. Collaborating with Crochet could bolster the Pirates' rotation alongside their promising arms like Paul Skenes and Jared Jones, providing a path toward returning to competitive form. As the Pirates seek to shift their approach, securing Crochet might signal a change in strategy moving forward.