The New York Yankees enter the 2025 Winter Meetings with a clear mandate: fortify the roster for a championship push, while being mindful of budget and recent injuries. Despite a 94-win season in 2025, the Yankees fell short in October (again) and now face a precarious rotation situation as three of five projected 2026 starters are set to begin the year on the injured list. General Manager Brian Cashman has signaled an emphasis on acquiring a high upside starting pitcher at a low salary cost, given the team’s self-inflicted payroll constraints and desire to avoid another mega-deal. At the same time, the Yankees are eyeing upgrades to the bullpen and lineup, targeting impact players who fit organizational needs without exorbitant salary commitments. Below, we evaluate five potential long-term trade targets who check those boxes and analyze why each could be a smart addition in the Bronx.
Sandy Alcantara
The Yankees’ top priority is pitching, and Alcantara offers frontline upside with a team-friendly contract. The 2022 NL Cy Young winner is coming off a challenging 2025, his first year back from Tommy John surgery, in which he logged a 5.36 ERA over 174.2 innings. However, that number is a bit misleading. The 30-year-old righty showed significant second-half improvement as he regained arm strength. In fact, from August 1 onward he posted a 3.70 ERA with a rising strikeout count, suggesting a return toward his ace form. Alcantara’s appeal lies in his proven durability and efficient, innings-eating style; prior to surgery, he led MLB in innings from 2019-2022 (over 858 IP) and averaged 6.6 innings per start. For a Yankees team that battled rotation injuries and overtaxed its bullpen, that reliability is gold.
Crucially, Alcantara is signed through 2026 at about $17.3 million per year (with a 2027 club option), a relative bargain for a potential CY Young starter. Miami is reportedly open to dealing him this winter after not receiving their asking price at last year’s trade deadline, especially now that his salary will top the Marlins’ payroll and their young arms are nearly MLB-ready. If the Yankees believe Alcantara’s late-2025 rebound is real, trading for him could secure a co-ace to pair with Cole in 2026 and beyond. His upside (15th-highest NL fWAR in 2023 even in a down year) and modest cost align perfectly with the Yankees’ offseason strategy.
MacKenzie Gore
Another route to bolstering the rotation is prying loose 26-year-old MacKenzie Gore, a former top prospect who may be entering his prime. The talented left-hander just completed back-to-back solid seasons for Washington, posting a 3.74 FIP in 2025 (after 3.53 in 2024) despite pitching in front of one of MLB’s worst defenses. His surface ERA (4.17) belied electric underlying numbers. Gore struck out 185 batters in 159.2 innings (a 27.2% K-rate), often looking like a front-line starter. Early in 2025, he even led all qualified pitchers with 13.63 K/9 and a 37.3% strikeout rate (97th percentile), underscoring the swing-and-miss quality of his repertoire. The Yankees covet this kind of whiff-generating arm, and Gore also does a good job keeping the ball in the park (around 0.9 HR/9 over 2024–25), a valuable trait for Yankee Stadium. Importantly, he’s still inexpensive and under team control through 2027, fitting the Yankees’ desire for upside without a hefty salary.
In New York, Gore could benefit from a stronger defensive team behind him (the Yankees were roughly league-average in defense in 2025, versus Washington’s bottom-tier ranking) and the club’s pitching development resources. His biggest weakness, a straight four-seam fastball that batters have hit well, could very well be improved under Matt Blake. Blake, the Yankees current MLB pitching coach and former Cleveland Guardians player development guru, has a long and successful track record of adding movement to fastballs. With two years of arbitration left, Gore would require a significant prospect haul, but he offers a rare combination of youth, strikeout stuff, and untapped potential. For a Yankees rotation suddenly thin at the top, Gore could slot in immediately and grow into a mainstay.
Josh Hader
While starting pitching is the headline need, the Yankees are also exploring bullpen upgrades and few relievers are more impactful than Josh Hader. The 31-year-old lefty closer is a luxury target, but his pedigree is undeniable: Hader was “his usual dominant self” in 2025, with a 2.05 ERA, 0.85 WHIP, 28 saves in 29 chances, and 76 strikeouts in 52⅔ innings. He overwhelms hitters with elite swing-and-miss stuff (his strikeout rate hovered in the mid-30s%, among MLB’s best) and in 2025 held opponents to a microscopic .219 expected Woba, basically rendering hitters helpless. Acquiring Hader would give New York a bona fide shutdown closer to anchor the late innings, something they’ve lacked at times. Beyond the gaudy K%, Hader brings the ability to go multiple innings when needed (he logged seven outings of more than 1.0 IP in 2025), which could be invaluable if the Yankees deploy bullpen games or face postseason scenarios requiring four-out saves.
There are hurdles: Hader is owed ~$19 million annually through 2028, and the Astros only signed him last year. However, Houston has a deep bullpen and an aversion to long contracts for pitchers and notably shut Hader down in August with a shoulder capsule strain. Hader has since rehabbed and says his shoulder is “back to normal,” with a regular offseason throwing program. If the Astros entertain offers, the Yankees could justify the cost: Hader’s track record (6 All-Star nods, 227 career saves) and continued excellence would instantly solidify New York’s bullpen. His presence would shorten games to eight innings and take pressure off guys like Camilo Doval and David Bednar. For a contender looking to win tight playoff games, an elite closer is a difference-maker, making Hader a compelling, if expensive, trade target.
Ketel Marte
On the position-player side, Ketel Marte emerges as an ideal fit for the Yankees’ lineup needs. The 32-year-old switch-hitter is coming off a fantastic 2025 season in Arizona, where he hit .283 with a .376 OBP, .517 SLG (.893 OPS) and 28 home runs, totaling roughly 4.4 WAR of value. Marte would inject balance and versatility into New York’s offense. As a switch-hitter with excellent contact skills (he struck out in only ~15% of plate appearances in 2025 while walking ~11%), Marte can lengthen a Yankees lineup that has sometimes been too right-handed and strikeout-prone. His advanced metrics support the production: Marte recorded a 47% hard-hit rate and .390 xwOBA last year, indicating his career-high power surge was backed by legitimate quality of contact. In other words, his 28 homers and .893 OPS were no fluke. Defensively, Marte has primarily played second base (104 games in 2025) but also has experience in center field and could be an option in left if needed.
The Yankees have a potential opening at the keystone depending on Jazz Chisholm Jr.’s status, and Marte’s bat would be a significant upgrade in that spot. He’s under contract through 2031 after a recent extension (owed $14M in 2025, escalating to the low-$20Ms in later years), which for his caliber is reasonable. Arizona may be reluctant to move him after a productive year, but if they pivot to a younger core, the Yankees should pounce. Marte’s well-rounded offensive profile of high contact, patience, and pop, is tailor-made for Yankee Stadium and the postseason. He’d give the lineup a jolt of consistency and playoff experience (Marte was the 2023 NLCS MVP), all without breaking the bank.
Bryce Eldridge
A more outside-the-box target for New York is Bryce Eldridge, one of the top power-hitting prospects in baseball. Eldridge, just 20, was San Francisco’s first-round pick in 2023 and has rocketed through the minors and even earned a September call-up in 2025 as the Giants made a late wild-card push. At 6’7”, 240 lbs., Eldridge is a towering left-handed first baseman often likened to a lefty Aaron Judge, and his scouting grades back it up: he boasts 70-grade raw power (on the 20-80 scale) and an overall future value of 60, projecting as an impact middle-of-the-order bat. In 2025, splitting time between Double-A and Triple-A as a 20-year-old, Eldridge slashed .249/.322/.514 with 18 homers in the upper minors. While he punched out quite a bit (his aggressiveness is a work in progress), he showed improvement late in the season, hitting .294 with 10 extra-base hits in his final 17 AAA games. The fact that Eldridge was ranked the Giants’ #1 prospect and a consensus Top 30 prospect in MLB by season’s end speaks to his ceiling. For the Yankees, targeting Eldridge would be about the long view: Ben Rice or Austin Wells could be moved for another piece, and the organization could use a next-gen first baseman with lefty power to slot behind Judge and Giancarlo Stanton in coming years.
Eldridge’s massive left-handed swing seems tailor-made for Yankee Stadium’s short right-field porch. Acquiring a prospect of his caliber would be costly and tricky, but San Francisco’s roster maneuverings (acquiring Rafael Devers) could make him a trade chip. New York’s interest would hinge on their willingness to part with significant prospect capital in return. If they do, Eldridge could become the next great Yankees slugger, aligning with their goal of balancing the present with the future. His upside, a potential 30+ homer, middle-order bat under club control for six+ years, is exactly the kind of high-reward target a team like the Yankees should be pursuing, even if it’s a move for down the road.
Each of these five targets brings something unique to the Yankees’ blueprint. Alcantara and Gore address the primary mission of fortifying the rotation with upside arms who won’t break the budget. Alcantara as a proven workhorse looking to regain ace status (on a fixed contract) and Gore as a blossoming strikeout artist entering his prime. Marte and Hader represent savvy “win-now” additions: Marte’s contact and power from both sides would diversify a feast-or-famine offense, and Hader would slam the door on tight games with playoff-level poise. Eldridge is a bold strategic play for the future, potentially securing the Yankees a cost-controlled slugger in an era where young star bats are gold. In all likelihood, the Yankees will prioritize pitching first. Expect their Winter Meetings war room to center on arms like Alcantara or Gore. The bullpen and lineup targets may depend on trade cost and what’s left in the budget after addressing the rotation. But the common thread is clear: New York is aiming to build a championship-caliber roster without taking on crippling contracts, instead leveraging trades to acquire talent aligned with their needs and timeline. Don’t be surprised if one of the starters is in pinstripes by the end of the Meetings, with a keen eye on Marte or Hader if the right deal emerges. By balancing immediate upgrades with long-term vision (as exemplified by Eldridge), the Yankees can emerge from the Winter Meetings having checked all the boxes, a deeper rotation, a mightier bullpen, a more balanced lineup, and positioned themselves as bona fide contenders for 2026.
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