The Boston Red Sox have already made two trades this winter for starting pitchers, with scale for more to come. This, of course, should be no surprise to any long-term observer of the franchise; the Sox have a pronounced favoritism for acquiring starting pitchers via trade during the Hot Stove Season dating back nearly thirty years. Remarkably, all of these deals have proven to be success stories for the Red Sox.
Nov. 18, 1997: Red Sox acquire Pedro Martinez (53.8 WAR for Boston) from Montreal Expos in return for Tony Armas (9.0 WAR for Montreal) and Carl Pavano (2.6 WAR).
Following the departure of longtime ace Roger Clemens, the 1997 Red Sox experienced a seven-game retreat in the win column despite the emergence of a young superstar shortstop in Nomar Garciaparra. That winter, general manager Dan Duquette did what many GMs do—he went fishing in familiar ponds. In this case, his previous employer, the Montreal Expos. Several years earlier, Duquette had traded for a young relief pitcher named Pedro Martinez, who immediately became one of the better starters in the National League. In 1997, he broke through into the highest echelon, winning the Cy Young Award at the age of 25 thanks to a major league best 1.90 ERA; his 305 strikeouts ranked second best in baseball, behind Phillies hurler Curt Schilling.
Penny-pinching Montreal could no longer bear the expense of such an excellent talent, opening the door for Boston. At the cost of two pitching prospects (neither of whom contributed much to the Expos), the Red Sox acquired Martinez in the earliest stages of his prime and made sure to extend him for the rest of it. Wearing red, Pedro won 117 games against only 37 losses in seven seasons, garnered two more Cy Youngs and placed in the top five three more times, solidifying his argument as the greatest pitcher of all time.
November 28, 2003: Red Sox acquire Curt Schilling (17.7) from Arizona Diamondbacks in return for Casey Fossum (-1.4), Brandon Lyon (2.1), Jorge de la Rosa (never played for Arizona in majors) and a minor leaguer.
Following a devastating defeat at the hands of the New York Yankees in the 2003 ALCS, general manager Theo Epstein set out to acquire a much-needed second ace to back up Pedro. The Arizona Diamondbacks, despite a World Series victory over the Yankees only two years before, were entering a rebuilding phase and looked to sell off their veteran assets, particularly their own second ace, Curt Schilling. As with the previous deal, Arizona in turn received a package of young pitchers, the best of whom (Jorge de la Rosa) made his mark with the Colorado Rockies in the early 2010s.
A no-trade clause complicated the fulfillment of the proposal, leading Epstein to make a personal pitch to the mercurial workhorse at Thanksgiving, detailing Schilling’s historic role in bringing a World Series victory to Boston. With Boston, a freshly extended Schilling did indeed fulfill this mission twice over, winning rings in 2004 and 2007, the latter his final big league season.
November 24, 2005: Red Sox acquire Josh Beckett (22.3) and Mike Lowell (10.6) from Florida Marlins in return for Hanley Ramirez (26.9), Anibal Sanchez (14.1), Harvey Garcia (0.1), and Jesus Delgado (0.0).
Following a disappointing conclusion to their championship defense, an aging Red Sox roster required retooling. The hero of 2004, Curt Schilling, had suffered a career-threatening ankle injury, leaving the top of the rotation ominously open for the first time since 1997. Amid front office confusion regarding Theo Epstein’s dramatic departure and apparently imminent return, the Red Sox made a trade with the penny-pinching Florida Marlins, just two years after they had beaten the Yankees in the World Series. The hero of that World Series, Josh Beckett, was now entering the final two years of arbitration, ensuring his retention beyond the club’s willingness to pay.
On Thanksgiving, the two teams made a blockbuster trade, Florida sending Beckett to Boston in return for top prospect Hanley Ramirez and three pitching prospects, including Anibal Sanchez. The Red Sox also took on the contract of apparently fading third baseman Mike Lowell.
Unlike Schilling and Martinez, Beckett did not prove an immediate success for the Red Sox; the team slid further back in 2006, missing the playoffs entirely, and their new ace posted an ERA of 5.01. 2007 more than made up for this disappointment, as Beckett emerged as a bulldog, winning 20 games in the regular season and four more in October as the Red Sox went on to win it all. His later years in Boston were mostly successful, yet he left town on a sour note as one of the principal offenders of the “beer-and-chicken” 2011 team.
December 11, 2014: Red Sox acquire Rick Porcello (8.0) from Detroit Tigers in return for Yoenis Cespedes (4.1), Alex Wilson (5.7), and Gabe Speier (never played for Detroit in majors).
The 2014 Red Sox proved as disappointing as the previous year’s squad had proven miraculous, despite the return of almost the entire roster. At the trading deadline, general manager Ben Cherrington chose to sell several pieces in return for major-league-ready talent, most notably ace Jon Lester for Oakland outfielder Yoenis Cespedes.
Cespedes performed well in August and September, but his true value to Boston came through a trade that December with the Detroit Tigers. In return for the Cuban outfielder and two relievers, the Red Sox acquired right-handed starting pitcher Rick Porcello, known for his youthful debut (20 years old and on the Opening Day roster in 2009) and ability to eat innings.
After a poor initial campaign, Porcello won the 2016 Cy Young Award on the strength of his 22 wins and strikeout-to-walk ratio of 5.91, both of which led the majors. His final three seasons as a Red Sox experienced extreme lows (he lost a major-league leading 17 games in 2017) and less extreme highs (17 wins for the 2018 team) as he returned to his previous standards. Nonetheless, Porcello remains the sole Red Sox pitcher to win a Cy Young since Pedro in 2000.
December 6, 2016: Red Sox acquire Chris Sale (17.0) from Chicago White Sox in return for Yoan Moncada (14.5), Michael Kopech (4.8) and two minor leaguers.
By 2016, the Chicago White Sox were in the middle of a lengthy rebuild and finally ready to sell off their finest asset in southpaw Chris Sale. The Red Sox, meanwhile, looked to take the next step towards a world championship by acquiring a true ace after David Price proved a mild letdown. Sale’s price turned out to be baseball’s top prospect in Yoan Moncada and hard-throwing Michael Kopech.
Once ensconced in Boston, the Red Sox had their most dominant starting pitcher since prime Pedro Martinez. In Sale’s first two seasons, he finished second and fourth in Cy Young voting, notched the sole 300 strikeout season by any Red Sox pitcher not named Pedro, and struck out Manny Machado to end the 2018 season. While injuries and an ill-fated extension diminished the remainder of his tenure, those two seasons alone more than equaled what Moncada and Kopech provided to the White Sox.
December 11, 2024: Red Sox acquire Garrett Crochet (6.3) from Chicago White Sox in return for Kyle Teel (1.9), Chase Meidroth (1.3), Winkelman Gonzalez (0.2) and Braden Montgomery.
By 2024, the Chicago White Sox were entering a lengthy rebuild and finally ready to sell off their finest asset in southpaw Garrett Crochet. The Red Sox, meanwhile, looked to take the next step from meandering at .500 towards genuine contention by acquiring an ace starting pitcher. Crochet required a heftier ransom than Sale did, as both Teel and Montgomery were Top 100 prospects, and the other two were major league-ready.
One year in, both teams should feel satisfied with their arrangement. Crochet followed his immediate predecessor and finished a close second in Cy Young balloting, leading the league in innings, strikeouts, and strikeout rate. Teel and Meidroth earned starting roles with their new teams, Gonzalez debuted as a potentially high-leverage relief option, and Montgomery reached Double-A ball in his maiden campaign as a professional.