New York — The New York Yankees enter a decisive offseason with urgent rotation concerns.
With Gerrit Cole and Carlos Rodón both sidelined to begin the 2026 campaign, the front office must act swiftly to reinforce its pitching depth.
Two surprise free agent pitchers enter the Yankees calculations after hitting the market this week. One struggled with home runs in the playoffs. The other returned from Tommy John surgery to post a 3.20 ERA. While one has drawn attention since officially entering free agency this week, the other appears to be the more practical and rewarding option for the Yankees.
Milwaukee starter emerges as prime target after declining team option
Brandon Woodruff officially declined his $20 million mutual option with the Milwaukee Brewers for 2026, opting instead for a $10 million buyout to explore the open market. The right-hander, a two-time All-Star, reestablished himself as a reliable starter in 2025 after missing the entire 2024 season recovering from Tommy John surgery. He went 7-2 with a 3.20 ERA in 12 starts, proving he could still perform at a high level.
According to MLB analyst Thaddeus Sawyer of DailyCampus, the Yankees could be the frontrunners to land Woodruff on a two-year, $34 million deal. Such a move would immediately give New York a proven mid-rotation starter to help stabilize the staff while Cole and Rodón continue their recoveries.
Woodruff’s track record speaks for itself. The 32-year-old owns a 53-28 career record with a 3.10 ERA across 142 appearances since being drafted by Milwaukee in the 11th round of the 2014 MLB Draft. He finished fifth in the National League Cy Young Award voting in 2021 and has logged eight postseason outings with a 3.18 ERA. His combination of experience and consistency makes him one of the most appealing arms available this winter.
Chicago ace’s surprise availability raises questions
The Cubs shocked baseball circles this week by declining their three-year, $57.75 million club option on left-hander Shota Imanaga. The 32-year-old then turned down his $15.25 million player option for 2026, making himself a free agent after only two seasons in Chicago.
Imanaga’s MLB debut season in 2024 was stellar. He compiled a 2.91 ERA over 173 1/3 innings, earned an All-Star nod, and placed fifth in the Cy Young race. But his follow-up season was less convincing. In 2025, he posted a 3.73 ERA across 144 2/3 innings, while his playoff numbers ballooned to an alarming 8.10 ERA in two appearances.
The Japanese lefty’s struggles grew more apparent as the year wore on. A hamstring injury disrupted his rhythm, leading to mechanical issues and inconsistent command. His home-run vulnerability was a particular concern, as he surrendered three long balls in just 6 2/3 innings between the Wild Card and Division Series. Those late-season challenges may make teams cautious about committing to him long-term.
Yankees rotation needs immediate reinforcement
The Yankees’ pitching staff faces immediate uncertainty. Manager Aaron Boone confirmed that Carlos Rodón won’t be ready for Opening Day after undergoing elbow surgery to remove bone spurs and loose bodies. Rodón, who went 18-9 with a 3.09 ERA in 2025, now faces a delayed start to his offseason preparation.
With Cole recovering, New York’s rotation currently hinges on Max Fried, Cam Schlittler, and Luis Gil. Clarke Schmidt remains an internal option, but depending solely on in-house arms would be a gamble for a team with championship expectations. Signing an experienced starter such as Woodruff could be the steadying move the Yankees need.
Contract projections favor Woodruff’s value
Financially, Woodruff presents a more balanced investment. His projected two-year, $34 million deal averages $17 million per season, offering the Yankees affordable reliability without long-term commitment. That structure aligns with the organization’s goal of maintaining payroll flexibility while still strengthening the roster.
Imanaga’s situation is far more uncertain. After the Cubs declined his three-year option, teams may hesitate to match or exceed that number due to his inconsistent second half and injury setbacks. Concerns about his durability and declining strikeout rate could limit his market, particularly among contenders wary of postseason lapses.
Woodruff’s recovery timeline aligns with Yankees needs
Woodruff’s bounce-back campaign following Tommy John surgery showcased not just his health but his resilience. Before Milwaukee’s NLDS matchup against Chicago, he shared that his connection to the city ran deep — his son was born there, and he called Milwaukee his second home. Still, his decision to enter free agency indicates he’s ready to embrace a new opportunity.
That perspective could fit perfectly with the Yankees’ situation. As a pitcher who’s endured and recovered from a major procedure, Woodruff brings a mindset that mirrors the patience and perseverance Cole and Rodón will need on their own comeback paths. His experience could also serve as an example within a rotation undergoing transition.
Statistical comparison reveals clear winner
The numbers heavily favor Woodruff as the more dependable option. Over eight MLB seasons, he’s maintained a 3.10 ERA with 10.4 strikeouts per nine innings and just 2.3 walks. His combination of command and swing-and-miss ability translates well to Yankee Stadium, where strikeout pitchers tend to thrive.
By contrast, Imanaga’s 2025 performance suggested some regression beneath the surface. His 4.86 FIP and 4.36 SIERA metrics indicated his 3.73 ERA might have been inflated by favorable batted-ball luck. Opponents adjusted to his rising fastball and splitter combination, tagging him for 23 home runs over his final 14 outings.
Qualifying offer complications could impact pursuit
Both free agents could still face qualifying offers from their former clubs. The Cubs have until Thursday to decide whether to extend Imanaga a one-year, $22.025 million qualifying offer. If he accepts, Chicago retains him for 2026; if not, his new team would forfeit draft compensation.
Milwaukee’s situation differs. Given Woodruff’s recent surgery and age, the Brewers are less likely to issue a qualifying offer. That factor could make him even more appealing to the Yankees, who would prefer not to lose additional draft picks after previous trades.
Veteran presence fits Yankees clubhouse culture
Woodruff’s professionalism, competitive edge, and postseason poise would blend seamlessly with the Yankees’ clubhouse. He has proven capable of handling pressure, a critical trait for anyone pitching under the lights of Yankee Stadium. His ability to stay composed and execute in October aligns perfectly with New York’s culture of accountability and big-game performance.
The Yankees value pitchers who thrive in demanding environments. Woodruff’s résumé suggests he can shoulder that responsibility, while Imanaga’s postseason inconsistencies raise doubts about his readiness for that stage.
Both pitchers bring intrigue to the Yankees’ offseason plans, but when weighing durability, cost, and performance under pressure, Brandon Woodruff stands out as the superior fit. His proven track record, steady command, and playoff-tested mentality make him the ideal candidate to stabilize New York’s rotation as the franchise looks to keep its championship window open in 2026.
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