The Chicago Cubs are have been known with potential of making high-stakes moves that reshapes their roster, all hinges on the New York Yankees’ desperation at this point. With ace Gerrit Cole sidelined for the season, the Yankees are scrambling to reinforce their starting rotation, and the Cubs are the perfect position to capitalize. One name swirling in trade talks is a talented standout veteran from the cubs, a key piece of Chicago’s rotation who is coming off one of the best years of his career.
The New York Yankees suddenly find themselves in dire need of reinforcements for their starting rotation after a devastating blow to their pitching staff. ESPN’s Jeff Passan reported that their ace, Gerrit Cole, is set to undergo Tommy John surgery on Tuesday, sidelining him for the entire season. This unexpected development forces the Yankees to explore all available options to fortify their rotation, whether through trades or the limited free-agent market.
With few reliable starters left in free agency, New York turns to the trade market to acquire much-needed pitching depth. While acquiring a high-profile arm like Dylan Cease would require a significant trade package, the Yankees could still land a quality starter without giving up their top-tier assets. One intriguing possibility comes from Heavy’s Michael DeFrancisco, who suggested that New York could look to reunite with Jameson Taillon by striking a deal with the Chicago Cubs.
Taillon, who posted a solid 3.27 ERA across 28 starts last season, is currently part of a crowded Cubs rotation. Given Chicago’s pitching surplus, he is a strong candidate to be moved. In terms of trade compensation, the Cubs are likely to evaluate the Yankees’ farm system, which MLB.com ranks as the 24th-best in baseball. While New York’s minor league depth is not highly regarded, they do have a few intriguing prospects that could entice Chicago.
One potential trade chip is right-handed pitcher Will Warren, the Yankees’ No. 5 prospect. Although Warren struggled in Triple-A last season, recording a 5.91 ERA over 109.2 innings, scouts believe his talent and raw ability could translate into future success with the right development. Trading him for a proven veteran like Taillon could be a worthwhile gamble for the Yankees, who are in immediate need of stability in their rotation.
Taillon is no stranger to the Bronx, having previously pitched for the Yankees in 2021 and 2022. Over his career, he has compiled a respectable 3.29 ERA across 201 games. His experience and consistency would provide a crucial boost to a Yankees rotation that is already stretched thin, especially with Luis Gil also dealing with an injury.
At the moment, Max Fried shoulders much of the burden for the Yankees’ rotation, and relying too heavily on unproven arms could prove costly as the season progresses. Adding Taillon would not only stabilize the rotation but also offer New York a much-needed veteran presence until Gil is ready to return.
Taillon is currently in the second year of a four-year, $68 million deal he signed with the Cubs in 2023. Given his strong performance last season, Chicago may see this as an opportunity to capitalize on his high trade value. With the Yankees now operating from a position of urgency, the Cubs could use this as leverage to extract the best possible return.
As the Yankees navigate the loss of Cole, the front office will have to act swiftly to prevent their championship aspirations from unraveling. Whether or not they reunite with Taillon, one thing is clear—the Yankees cannot afford to stand pat as the season approaches.
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