**Yankees Grapple with Decision on Gerrit Cole's Future Ahead of Deadline**

As the clock approaches the 5 p.m. Eastern deadline, the New York Yankees face a crucial decision: whether to extend Gerrit Cole’s contract by adding a fifth year at $36 million or let him head to free agency. This decision boils down to which side holds the leverage.

If Cole holds the leverage, it’s because of his exceptional pitching abilities. Cole is a rare asset, capable of enduring multiple lineup cycles and consistently delivering strong performances, even in the highest-stakes games. The Yankees, having returned to the World Series for the first time in 15 years, are keenly aware of Cole’s value, especially as Aaron Judge approaches his 33rd birthday. Retaining Cole means securing one of the best pitchers in the world and potentially earning him a place in Monument Park with a retired No. 45 jersey.

On the other hand, if the Yankees have the upper hand, it’s due to several concerns about Cole’s future. Cole turned 34 in September, and his recent elbow injury limited him to just 19 starts this past season, yielding a 3.41 ERA—his worst since leaving the Pittsburgh Pirates for the Houston Astros. Additionally, his strikeout rate has declined over the past three years. The Yankees might view the opt-out as an opportunity to negotiate a more favorable contract or move on before Cole's performance declines further.

Potential suitors for Cole, should he enter free agency, include big-spending teams like the Phillies, whose owner John Middleton has a history of striking deals with Scott Boras, Cole's agent. The Cubs might also consider making a significant financial commitment. However, there are concerns about whether these teams could meet Cole’s expectations for both salary and championship aspirations, particularly given his recent health issues.

Comparisons to pitchers like Max Scherzer, who experienced a decline in performance after age 33, provide further reasons for the Yankees' caution. If the Yankees decide to let Cole go, they face uncertainty with a rotation that includes Nestor Cortes, Luis Gil, Carlos Rodon, Clarke Schmidt, and Marcus Stroman—none of whom hold the same reliable ace status as Cole.

Ultimately, the Yankees must weigh the risks of retaining an aging and injury-prone ace against the uncertainty of replacing him. Both sides have substantial stakes in this decision, which could lead to a last-minute compromise or a definitive move into free agency for Cole. The outcome will hinge not only on financial terms but on the broader strategic vision for the Yankees' future success.