Yankees notch a strategic win with Gerrit Cole’s contract U-turn

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While Yankees General Manager Brian Cashman portrayed a diplomatic approach regarding Gerrit Cole’s contract situation, the dynamics revealed a more complex reality. The team successfully kept their ace without increasing their financial commitment, despite the option to secure him with an additional fifth year at $36 million. This outcome represents an early win for the Yankees as they look ahead to the 2025 season, particularly following their World Series disappointment in 2024.

Cashman explained that the decision to extend the negotiation deadline was driven by time constraints after the World Series. He noted that productive discussions among all parties involved—himself, agent Scott Boras, owner Hal Steinbrenner, and Cole—resulted in the agreement to allow more time for negotiations.

“Maybe the grass isn’t always greener,” the Yankees GM said on Monday. “I think he’s happy where he’s at. I think he likes our setup. I think he likes who he’s playing for and working for, and I think he likes his teammates. And I think he think we have a legitimate chance to win.’’

While Cashman hinted at the possibility of future contract extension talks, he indicated that such discussions would only advance if they were financially advantageous for the Yankees. This could involve reduced annual salaries or deferred payments to mitigate luxury tax implications.

“It was something at the moment we weren’t necessarily comfortable doing,” Cashman explained. “But we wanted our players and ace back, and he certainly didn’t want to go. We had a lot of healthy dialogue about just trying to thread the needle and keep it in play. We could always talk further as we move forward about the future because the intent when we signed Gerrit was that he’d be leading our staff until the end of his career.”

The Yankees’ firm stance at this crucial moment, when Cole could have opted for free agency, signals their intention to maintain this approach throughout the remainder of his four-year contract, which extends through age 37 unless any modifications align clearly with their interests.

Although Cashman downplayed the notion of a strategic standoff during negotiations, the outcome closely aligned with the Yankees’ objectives. Cole’s decision to opt out seemed to test the organization’s willingness to improve its contract terms, a strategy that ultimately did not succeed.

Why Cole’s contract drama could favor Yankees

Cole’s contract negotiations bring attention to the Yankees’ upcoming talks with another Scott Boras client, Juan Soto, but the circumstances differ greatly. Unlike Cole or Aaron Judge, Soto does not have existing ties with the Yankees. At just 26 and in his prime, Soto is expected to attract strong competition from multiple teams, positioning his market differently from Cole’s recent negotiation period.

General Manager Brian Cashman addressed the team’s initial hesitation over extending Cole’s contract to 2029 at $36 million but noted that keeping their ace remained a priority. Cashman pointed out that replacing Cole would be difficult, even with standout free-agent pitchers such as Corbin Burnes, Max Fried, Blake Snell, and potentially Roki Sasaki available. The uncertainty surrounding how they might adapt to the unique pressure of New York highlighted the advantage of retaining Cole, who has already excelled in that environment. Cashman spoke of Cole as being deeply integrated into the Yankees organization, likening him to family.

With Aaron Judge turning 33 in April, the Yankees remain committed to their win-now approach. Cole’s continued presence aligns with that mindset and could ultimately lead to his number 45 being retired, should his performance stay at an elite level over the next four years. Cashman confirmed the franchise’s goal of building the roster around the Judge-Cole core.

Cashman described the deal as something both sides wanted, aiming to keep the partnership intact. Still, beneath the mutual agreement were practical elements: the Yankees’ reluctance to make an automatic $36 million extension and Cole’s concerns about his open-market prospects.

Cole’s current performance trends raise some significant concerns for the Yankees. Now 34, he dealt with elbow trouble that limited him to 19 starts, and his 3.41 ERA was his highest since leaving Pittsburgh for Houston. His strikeout rate has also shown a steady decline over the past three seasons, dipping from 32.0% to 27.0% and then to 25.4%—coinciding with the crackdown on illegal pitching substances.

The decision to keep Cole had wider implications for the Yankees. Letting go of a proven ace would have sent a message across the league about caution and risk management. Concerns about Cole’s durability remain valid, given his extensive career workload surpassing 2,000 innings, including postseason outings. How he performs over the next few years, from ages 34 to 38, is uncertain compared to his output during his prime from 29 to 33.

Baseball Reference’s similarity scores draw comparisons between Cole’s current trajectory and Max Scherzer’s career. Scherzer had a decade of reliable 30-start seasons through age 33 but only one such season afterward, excluding the shortened 2020 season. While Scherzer still delivered high-quality pitching when healthy, his frequency of starts and overall impact waned.

While there was speculation that teams like the Mets, Phillies, or Orioles might entertain a $180 million bid for the Yankees ace, such interest remained hypothetical. It was also unclear if Cole would want to start over with a new team at this point in his career.

Internally, the Yankees’ rotation depth presented challenges: Nestor Cortes nearing free agency after dealing with elbow issues, and a mix of Luis Gil, Carlos Rodon, Clarke Schmidt, and Marcus Stroman—whom GM Brian Cashman had previously regarded as insufficient for postseason success. Thus, keeping Cole proved to be the more viable option, especially without committing to an additional $36 million for 2029.

Securing Cole ahead of potential offseason chaos marks an early win for the Yankees as they look to the 2025 season, though the true test will come on the field.

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