In 2003, the Boston Red Sox finally fought their way back into the postseason after spending three long years wandering outside the October spotlight. For a franchise that had built a reputation on heartbreak, suffering, and near-misses, simply qualifying for the playoffs felt like a long-awaited step forward. Yet that sense of renewal quickly morphed into another chapter of frustration when Boston collided with its greatest nemesis the New York Yankees in an American League Championship Series that stretched the full seven games and ended in a crushing loss. Red Sox fans will forever remember that season for its promise, its drama, and the lingering feeling that the team needed just one more push to climb the mountain.
Fast-forward to 2025, and history once again seemed to rhyme for the Red Sox. After missing the playoffs from 2022 through 2024, the club clawed its way back into contention under a new front office and a retooled roster. But just as in 2003, that long-awaited return to October baseball ended the same painful way: with a postseason defeat at the hands of the Yankees. This time, it happened in the AL Wild Card Series, which Boston lost in three tightly contested games. And once again, the organization finds itself staring at an opportunity and perhaps a necessity to make a bold, defining upgrade to the pitching staff.
Back in 2003, that urgency led then-general manager Theo Epstein to search aggressively for an elite starter to pair with the club’s icon and unquestioned ace, Pedro Martinez. Epstein believed that without a second dominant arm at the top of the rotation, Boston’s pursuit of a championship would continue to fall short. That search culminated in one of the most significant trades in franchise history. On Thanksgiving of that year, Epstein convinced veteran right-hander Curt Schilling then 37 years old and a perennial Cy Young candidate to waive his no-trade clause and approve a deal that would bring him to Fenway Park. Schilling had been starring for the Arizona Diamondbacks, but the team was stuck in a decline and ready to retool.
Boston surrendered four prospects in order to pry the flamethrowing righty away from Arizona, and the payoff became the stuff of legend. Schilling, teaming with Martinez, powered the Red Sox to their first World Series championship in 86 years, forever altering both the franchise’s trajectory and Schilling’s legacy. That acquisition marked the beginning of a new era one defined by aggressive roster-building, bold front-office decisions, and the long-awaited collapse of the so-called “Curse of the Bambino.”
Now, more than two decades later, Boston appears to be standing at a similar crossroads. With Thanksgiving approaching once again, and with current chief baseball officer Craig Breslow clearly stating his intention to add another front-line starting pitcher to pair with this year’s emerging ace Garrett Crochet, the parallels to 2003 have grown impossible to ignore. FanSided analyst Christopher Kline even suggested that Boston could target another 37-year-old power pitcher, Texas Rangers star Jacob deGrom.
While the Rangers have not publicly declared deGrom available, their circumstances mirror those of the early-2000s Diamondbacks in striking ways. Texas is just two seasons removed from its first-ever World Series title, yet it followed that championship with an average, 81-win campaign in 2025. Injuries, roster turnover, and aging stars have pushed the Rangers closer to a reset cycle, and the organization is widely viewed as a team that may soon start prioritizing young assets rather than headline-grabbing veterans. That shift could make a deGrom trade at least plausible, especially given that the Red Sox possess a deep farm system stocked with the types of prospects Texas may covet.
Kline laid out the logic behind the hypothetical fit in a Monday analysis piece. “Craig Breslow has laid bare his intention to pursue top starters to pair with Garrett Crochet atop the rotation,” he wrote. “He won’t have many better options than deGrom, who brings over a decade of sensational results to the table. 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.”
For any team looking to add an elite pitcher, Jacob deGrom’s résumé all but speaks for itself. With Clayton Kershaw officially retired after the 2024 season, deGrom now stands alone as the active pitcher with the lowest career ERA among those who have thrown at least 1,000 innings. His 2.57 ERA places him in rarefied air — and underscores just how dominant he has been when healthy. Formerly a ninth-round draft pick of the New York Mets, deGrom rose from modest expectations to become one of the most overpowering arms of his generation. He owns two Cy Young Awards, captured the 2014 National League Rookie of the Year honor, and has repeatedly rewritten the standards for efficiency and command.
One statistic stands above all the rest: deGrom’s career strikeout-to-walk ratio, an astonishing 5.37-to-1, is the highest in MLB history. Few pitchers have ever combined that level of precision with such overwhelming velocity and movement. When he’s on the mound, he is as close to automatic dominance as any pitcher in the modern era.
Of course, the primary question surrounding any pursuit of deGrom is not about talent it’s about durability. Injuries have limited him significantly in recent seasons, making any trade a heavy gamble. Yet for a team like Boston, which may be one piece away from vaulting into legitimate championship contention, the upside could be enormous. And because of Texas’ organizational needs, the cost of acquiring deGrom would almost certainly revolve around pitching prospects, particularly left-handed arms.
According to MLB Pipeline, six of the Rangers’ top 10 prospects are right-handed pitchers. That imbalance could push Texas to demand lefties specifically in any major trade. For the Red Sox, that likely means the centerpiece of any offer would be Payton Tolle the No. 2 overall prospect in the system and perhaps the most physically imposing pitcher in Boston’s entire development pipeline. Tolle stands at 6-foot-6, weighs 250 pounds, and features a powerful repertoire that has drawn attention across the league. His ceiling is high enough that including him in a deal would be a significant sacrifice for Boston’s long-term rotation plans.
But Tolle alone would not be enough. Texas would almost certainly insist on a second left-handed pitching prospect, likely forcing Boston to choose between two other top-10 arms: Brandon Clarke, the fifth-ranked prospect in the system, or Connelly Early, who sits just behind him. Clarke, a fifth-round pick in 2024, is only 22 years old and has already shown the polish and athleticism of a potential mid-rotation starter. Early, meanwhile, brings something neither Tolle nor Clarke can offer: major league experience, including postseason innings.
Early’s brief time in the big leagues has been highly impressive. After a stellar collegiate career at Virginia, he made four regular-season starts for Boston in 2025, posting a 2.33 ERA with 29 strikeouts and just four walks across 19⅓ innings. When the Red Sox reached the postseason, Early was the club’s choice to start the decisive Game 3 of the Wild Card Series. That assignment demonstrated how much the organization already trusts him and how quickly he has climbed the depth chart. For that very reason, Texas would likely view him as a highly attractive trade piece.
The looming question, then, is whether Craig Breslow and the Red Sox front office would truly be willing to sacrifice such valuable pieces of the organization’s pitching future in exchange for a chance at immediate championship contention. Trading a prospect like Tolle let alone Tolle plus Clarke or Early would represent one of the most aggressive moves Boston has made in years. But so did the decision to trade for Curt Schilling in 2003. And in retrospect, that deal became the cornerstone of a championship transformation.
Baseball history often turns on moments when a front office decides to push its chips all in. The Red Sox have a recent blueprint one that turned into a title. The circumstances are piling up in eerily similar fashion: a return to the postseason after a three-year drought, a stinging October loss to the Yankees, an emerging ace needing a co-headliner, a 37-year-old superstar pitcher potentially within reach, and a Thanksgiving timeline that feels ripped straight from the early 2000s.
Whether Breslow will follow the Epstein playbook remains to be seen. But if the past is any indicator, the days immediately following Thanksgiving may reveal exactly how far the Red Sox are willing to go to pursue a title in 2026. Boston’s baseball future could hinge on whether the organization dares to repeat the boldness of 2003 and whether Jacob deGrom becomes the modern equivalent of Curt Schilling.
