In 2003, the Boston Red Sox returned to the postseason after three years in the wilderness, only to come up short when they lost to the New York Yankees in an American League Championship Series that went the full seven games.
In 2025, the Red Sox again ended a three-year playoff absence only to lose to the Yankees in the postseason once again, this time in an AL Wild Card Series that went the full three games.
Determined to make a great leap forward in 2004, Boston’s general manager at the time, Theo Epstein, knew the Red Sox needed a second front-line starting pitcher to pair with the staff ace, Pedro Martinez. On Thanksgiving in 2003, he persuaded 37-year-old power-pitching right-hander Curt Schilling to forego his no-trade clause with the Arizona Diamondbacks and accept a move to Boston.
The Red Sox sent a package of four prospects to Arizona and the rest is Boston history. Schilling and Martinez propelled the Red Sox to their first World Series championship in 86 years.
Will History Repeat For Red Sox?
Could history repeat itself? With Thanksgiving only a week away and current Red Sox chief baseball officer Craig Breslow openly declaring his aim of acquiring a second front-line starter to pair with ace Garrett Crochet, the Red Sox could target another 37-year-old power pitcher, Jacob deGrom of the Texas Rangers, according to FanSided analyst Christopher Kline.
The Rangers have not stated their intention to trade deGrom, but after an 81-win season just two years removed from the franchise’s first World Series title â a similar situation to Schilling’s Diamondbacks who won just 84 two years after their 2001 championship â the Rangers appear to be in a rebuild period and should be in the market for prospects, a commodity the Red Sox own plenty of.
“Craig Breslow has laid bare his intention to pursue top starters to pair with Garrett Crochet atop the rotation. He won’t have many better options than deGrom, who brings over a decade of sensational results to the table,” Kline wrote on Monday. “His experience as a right-handed ace could pair nicely with a more green lefty in Crochet, giving the Boston Red Sox both a productive second ace and a valuable leader in the clubhouse.”
Jacob deGrom: History-Making Hurler
With the retirement of Los Angeles Dodgers future Hall of Famer Clayton Kershaw, deGrom now owns the lowest lifetime ERA of any active pitcher (minimum 1,000 innings pitched) at 2.57.
The former New York Mets ninth-round draft pick â a two-time Cy Young Award winner and 2014 National League Rookie of the Year â also holds the all-time record for career ratio of strikeouts to walks, fanning 5.37 for every free pass he has issued.
Were the Rangers to trade deGrom, they would likely be looking for pitching prospects in return â specifically left-handed pitchers, because of the top 10 Texas prospects according to MLB Pipeline, six are right-handed pitchers.
Boston’s Top Southpaw Prospects in Proposed Deal
The Red Sox would in all likelihood be required to give up their No. 2 overall prospect, 6-foot-6, 250-pound left-hander Payton Tolle, as well as either 22-year-old No. 5-ranked Brandon Clarke â Boston’s fifth-round pick in 2024 â or Connelly Early, ranked one step below Clarke.
Early has the benefit of big league experience, including in the postseason. Early started the deciding Game 3 of the AL Wild Card Series this year. In four regular-season starts, the 23-year-old former Virginia Cavalier posted an impressive 2.33 ERA, striking out 29 with only four walks in 19 1/3 innings.
Would Breslow and the Red Sox give up a significant piece of Boston’s pitching future to become instant World Series contenders by adding deGrom? If history is any indicator, the answers could become clear sometime shortly after Americans sit down for their Turkey Day dinner.
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