With news breaking today that Yankees Ace pitcher Gerrit Cole is out for the year while he undergoes Tommy John surgery, many have speculated the Yankees will act quickly to trade for another starting pitcher. One possibility could be current Cubs starter, and former Yankee, Jameson Taillon.
Jameson Taillon had a very good 2024 season. He posted his best season since his 2018 breakout campaign. Last season for the Cubs Jameson Taillon pitched to the tune of a 3.27 ERA, 122 ERA+, and 12-8 record. Taillon enters 2025 as the Cub’s clear number three starter behind Shota Imanaga and Justin Steele.
The Yankees may be desperate
So why would the Cubs want to trade him? Especially given their current dilemma at the bottom of the rotation? The answer is simple: the Yankees may be desperate. The Yankees will be looking to make their way back to the World Series this year, and that will now be much harder without their ace. While they did sign Max Fried in the offseason their pitching depth still is an area of concern. Why not trade for a quality pitcher with a reasonable salary coming off a great season? Additionally, they have familiarity with Taillon, as he pitched in the Bronx in ‘21 and ‘22 with a combined 4.08 ERA.
The desperation for a new starting pitcher makes sense for the Yankees. But how could that benefit the Cubs? While it’s true that the Cubs are trying to seriously contend this year and they also don’t have many reliable starters after Taillon, they could play the long game.
Are the Cubs willing to move Taillon?
So what gives? For starters, it would clear the remaining 2 years and $36 million of Taillon’s contract off the books. That money could be used to upgrade several positions during this season and/or be rolled over into the next offseason. But perhaps the main reason is that they could get excellent value for Taillon. The Cubs reportedly shopped him during the last trade deadline but couldn’t find any suitors.
But coming off a good season and having two years left of control, his value might be at an all-time high. The Cubs’ MO during the Jed Hoyer era has been to trade veterans for talented young players and prospects. Take for example Mark Leiter Jr., David Robertson, Cody Bellinger, and the entire 2021 deadline. The Cubs would likely take the same approach with a potential Taillon trade this season.
In terms of compensation, the Cubs would first look at the Yankee’s farm system. According to MLB.com, the Yankees sport the 24th-ranked farm in all of baseball. Not great, but they still have a few players that would catch the Cub’s attention.
One may be pitcher Will Warren who made his major league debut last year. His stats in Triple-A last season were suspect posting a 5.91 ERA in 109.2 innings, but the stats may not tell the full story on Warren. He is a talented pitcher who could one day be a great starter with the right development.
The Cubs may also inquire about pitcher Ben Hess, the Yankee’s number four-rated prospect. The twenty-two-year-old is exactly the type of acquisition Jed has become known for, the young player who hasn’t ascended the minor league ranks just yet.
This trade scenario is hypothetical and not at all a report. But if the Cubs are smart they may want to give a call to New York to see if they could fleece some young talent and take advantage of their desperation.
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