The Red Sox are “in a good position” to trade for $18 million for the left-hander Cy Young according to Top MLB Insider amid internal turmoil at the Red Sox
As the MLB offseason heats up following a disappointing early playoff exit, the Boston Red Sox find themselves at a crossroads. Whispers of blockbuster trades are growing louder, with one particularly tantalizing rumor dominating headlines: a potential deal to acquire Detroit Tigers ace Tarik Skubal, the reigning American League Cy Young winner and a frontrunner to repeat the honor in 2025. According to longtime ESPN insider Buster Olney, the Red Sox are “well positioned” to make a run at the 28-year-old left-hander, whose projected arbitration salary for next season hovers around $18 million. This move could transform Boston’s rotation into a juggernaut, but it comes at a time when the organization grapples with mounting internal challenges that threaten to derail their momentum.
Skubal’s dominance on the mound has been nothing short of electric. In 2025, the southpaw posted a blistering 13-6 record with a 2.21 ERA over 195 innings, striking out 241 batters while maintaining a WHIP of just 0.891. These numbers not only solidified his status as the AL’s premier pitcher but also echoed his breakout 2024 campaign, where he claimed the Cy Young with similar flair. With only one year of team control remaining before free agency, Detroit faces a dilemma: lock him up long-term or cash in on a trade windfall. Olney, in a recent column, suggested the Tigers are open to the latter, especially if the return package includes major-league-ready talent. “Other teams believe the Tigers will seriously consider moving him if they can glean what they want in a trade—and there is every reason to expect a significant bidding war,” Olney wrote.
For the Red Sox, landing Skubal would pair him seamlessly with their existing ace, Garrett Crochet, who himself emerged as a Cy Young finalist in his debut Boston season. Acquired in a blockbuster trade from the Chicago White Sox last winter and promptly extended for six years at $170 million, Crochet dazzled with an 18-5 mark, a 2.59 ERA, and a league-leading 255 strikeouts across 205 1/3 innings. The duo would form the most fearsome one-two punch in baseball, capable of overwhelming lineups and anchoring postseason hopes. Boston’s pitching staff ranked fourth in MLB with a 3.70 ERA this year, but depth issues exposed vulnerabilities in the playoffs, particularly after a first-round loss to the New York Yankees. Chief baseball officer Craig Breslow has made no secret of his desire to bolster the rotation, and sources indicate trading for a controllable arm like Skubal aligns perfectly with the team’s philosophy of building through prospects rather than splurging in free agency.
What makes Boston such an attractive suitor? Their farm system remains one of baseball’s deepest, stocked with high-upside talent that could entice Detroit. MLB Pipeline ranks the Red Sox’s system among the top three, headlined by shortstop Marcelo Mayer (No. 9 overall prospect) and outfielder Roman Anthony (No. 11). A hypothetical package might include outfielder Jarren Duran—a 2025 All-Star with 25 homers and elite speed—alongside first-round draft pick Kyson Witherspoon, a 21-year-old right-hander rated as the No. 10 prospect in last summer’s class. Other pieces like infielder Kristian Campbell or lefty Brandon Clarke could sweeten the deal, allowing Boston to preserve their untouchable core while parting with mid-tier assets. Analysts like Jim Bowden of The Athletic have echoed Olney’s sentiment, noting the Red Sox’s “plenty of prospects in their strong farm system to perhaps trade for top arms like Tarik Skubal.” Financially, Boston has flexibility too, with over $21 million coming off the books from Walker Buehler’s contract and potential opt-outs from Lucas Giolito, freeing up payroll for an extension to keep Skubal beyond 2026.
Yet, amid this tantalizing prospect, the Red Sox are navigating a storm of internal discord that could complicate negotiations. The 2025 season, while marking Boston’s first playoff appearance since 2021, was marred by controversy. The midseason trade of franchise cornerstone Rafael Devers to the San Francisco Giants—a deal that netted pitching prospects but stunned fans—ignited backlash. Devers, a three-time All-Star and lifelong Red Sox, was shipped out amid stalled extension talks and whispers of clubhouse friction over his defensive lapses at third base. The move freed up $75 million over the next three years but left a void in leadership and power, contributing to a lineup that ranked 22nd in home runs. “It felt like betrayal,” one anonymous player told The Athletic, highlighting the emotional toll.
Compounding the unease, labor tensions erupted at Fenway Park in June when 95% of stadium union workers voted to authorize the first strike in the ballpark’s storied history. Demands for better wages and working conditions amid rising costs stalled operations briefly, forcing management to scramble. On the field, injuries ravaged the roster: top prospect Mayer missed significant time with a wrist issue, forcing awkward positional shifts for Ceddanne Rafaela and Duran. Off-field, the front office overhaul under Breslow—fresh off signing Alex Bregman to a $120 million pact—has bred uncertainty. Reports surfaced of clashes between scouts and analytics staff over prospect evaluations, with some insiders questioning Breslow’s aggressive spending after the Devers fallout. Manager Alex Cora, extended through 2027, has publicly urged unity, but the end-of-season press conference revealed strained smiles. “We’re rebuilding trust, on and off the diamond,” Cora said, a veiled nod to the turmoil.
These fractures have fueled speculation that Boston’s aggressive pursuit of Skubal is as much about stabilizing the ship as upgrading the roster. A coup like this could rally fans, quiet critics, and signal Breslow’s commitment to contention. However, rivals like the Yankees and Orioles lurk, armed with deeper pockets and fewer distractions. If Detroit prioritizes position players, Duran’s inclusion might tip the scales, but Mayer’s no-trade clause adds another layer of complexity.
As free agency looms and the Winter Meetings approach, the Red Sox stand on the precipice. Skubal represents not just an ace, but a statement: that despite the chaos, Boston remains a sleeping giant ready to roar. Whether they pull off the deal—or if internal rifts prove too deep—will define their trajectory. For now, in a city starved for October glory, hope flickers amid the uncertainty. The lefty’s fastball could light the fuse.
