This is part two of a two-part series that focuses on predicting offseason moves for the New York Yankees during the 2025-26 offseason. Part two focuses on free agency and trades following the decisions from part one.
Doubling down in the rotation
The Los Angeles Dodgers had four all-star pitchers start a World Series game, while the Toronto Blue Jays had three. The current Yankees rotation would feature one.
With ace Gerrit Cole projected to be out until midseason and Carlos Rodón also set to miss the start of the year, the Yankees would be wise to add at least one all-star caliber starter to stabilize the rotation. Barring injury, Max Fried will start on Opening Day. Cam Schlittler and Luis Gil likely have their rotation spots cemented, with Will Warren rounding out current established options.
While signing an ace in the top-heavy market is unlikely, there are still viable options towards the middle of the market. One option is Brewers starter Brandon Woodruff, who just declined a $20 million player option for 2026.
Woodruff started 12 games in 2025 while battling injuries but was a productive mid-rotation option when available. The two-time all-star pitched to a 3.20 ERA while limiting free passes. A two-year, $34 million contract would give the Yankees a second established option to begin the season and depth even after Cole, Rodón and Clarke Schmidt return.
Final Prediction: Woodruff (2 years, $34 million)
Rebuilding the bullpen
While Mets closer Edwin Díaz became a free agent after opting out of the remaining two years and $28 million remaining on his contract, he will likely command over $100 million for the second time in his career. The last time the Yankees neared that level for a reliever was to reunite with Aroldis Chapman in December 2016 on a five5-year, $86 million deal.
The next best free agent option is San Diego Padres closer Robert Suárez. Suárez is coming off a career year in which he posted a career high 40 saves and kept his ERA under 3.00 for the third time in four seasons.
Suárez’s pitch usage is quite similar to that of the departing Luke Weaver, throwing their fastballs at an almost identical rate and their changeups within 10 percent of each other. Suárez also mixes in a sinker 15 percent of the time, giving him a valuable third look for the postseason.
The righty will pitch all next season at 35-years-old, meaning that he will be limited to a shorter deal than Díaz. As such, a three-year contract with an average annual value of around $17 million would give the Yankees another high-end option without sacrificing long term flexibility.
With a big-ticket free agent bullpen acquisition accounted for, the Yankees could next turn to a trade market where the best option is longtime Tampa Bay Rays reliever Pete Fairbanks. Often the center of trade speculation, a move finally seems likely this offseason with the Rays missing the playoffs in 2025 and Fairbanks’ contract set to expire after 2026.
Since 2019, Fairbanks hasn’t posted a FIP above 3.63. In three seasons as the fulltime closer, the right hander has accumulated 75 saves. The 31-year-old appeared in a career high 61 games in 2025.
Despite the potential trade being in-division, the Rays and Yankees linked up at the 2025 deadline in the deal that José Caballero to New York. Fairbanks, who would cost the Yankees $12.5 million next season, would probably fetch a similar package to the one New York gave up for Devin Williams last offseason.
A package including Chase Hampton, a 24-year-old right hander who is recovering from Tommy John surgery but was formerly a top 100 prospect who should be Major League ready soon after his rehab concludes, and Roderick Arias, another former top 100 prospect infielder who is just 21-years-old, but has struggled at the plate in three out of four seasons in the minor leagues, could be enough to get a deal done.
To fill two other open spots, the Yankees may look for reclamation projects on minor league contracts, á la Weaver in 2024. Internal options include Yerry De los Santos, Brent Headrick and Allan Winans, amongst others.
Final Prediction: Suárez (3 years/$51 million), Yankees acquire Fairbanks ($12.5 million) from the Rays in exchange for RHP Hampton, INF Arias
Finding a long-term third base fix
The Yankees’ acquisition of Ryan McMahon from the Colorado Rockies shored up the infield defense but seems more like a band aid than a long-term fix due to his light bat.
Moving part of McMahon’s contract would afford the Yankees extra financial flexibility, but his bloated deal that runs past 2026 will be hard to move. That commitment could very likely keep New York from shopping at the top of the market for names such as Alex Bregman and Munetaka Murakami.
Instead, a look at the trade market shows that Cardinal’s infielder Brendan Donovan is available with St. Louis beginning a long term rebuild. In Donovan, the Yankees would receive a versatile defender who got on base at a .353 clip in 2025. That number was only the third highest of his four-year career, meaning that New York would be adding a bonafide on-base machine for the top of their lineup.
While Donovan has only played 46 games in the major leagues as third baseman, the Cardinals trusting him at shortstop multiple times in the past suggests that a move to the hot corner shouldn’t be too much to handle for the 28-year-old former Gold Glove recipient.
Donovan is controllable for two seasons, with a projected $5.4 million arbitration salary in 2026, meaning that the Yankees will have to part with a decent package to acquire his services. In this scenario, New York deals top 100 prospect Spencer Jones. The power-hitter struggles with strikeouts and is currently blocked at the Major League level but has the potential to be a top of a lineup bat for the next half decade. Pitching prospect Thatcher Hurd rounds out the package.
Final Prediction: Yankees acquire Donovan ($5.4 million) from the Cardinals in exchange for OF Jones and RHP Hurd
Projected 2026 Opening Day roster
Starting pitchers (5): Fried, Gil, Schlitter, Warren and Woodruff
Bullpen (7): David Bednar (RHP), Fernando Cruz (RHP), Camilo Doval (RHP), Fairbanks (RHP), Tim Hill (LHP), Suárez (RHP), De los Santos (RHP) and a MiLB free agent/depth pitchers left-hander
Lineup (9): Donovan (3B, LH), Cody Bellinger (LF, LH), Aaron Judge (RF, RH), Jazz Chisholm Jr. (2B, LH) Giancarlo Stanton (DH, RH), Ben Rice (1B, LH), Anthony Volpe (SS, RH), Austin Wells (C, LH) and Jasson Dominguez (CF, SH)
Bench (5): Oswaldo Cabrera, Caballero, McMahon, and Amed Rosario
Final Approximate Payroll: $314 million
Arbitration predictions from MLB Trade Rumors
Market Value Predictions/AAV estimates from Spotrac