The Yankees’ postseason exit has already pushed the conversation toward what comes next, and that’s where the trade market gets interesting. If New York decides it needs an offseason reset, the Cubs could be lurking as a logical partner - especially with Chicago staring at a long winter of its own, one centered on rebuilding a pitching staff that underperformed, got hit by injuries and is headed for major turnover in free agency.
That overlap opens the door to a familiar kind of deal between the two clubs. And if the Yankees get creative, there are three arms who could wind up on the Cubs’ radar.
Luis Gil is the name that jumps out first. Just two seasons removed from his 2024 AL Rookie of the Year campaign, the right-hander’s stock has taken a hit fast.
That year, he struck out more than 10 batters per nine, made 29 starts and posted a 3.50 ERA across 151 2/3 innings. But 2025 and 2026 told a much rougher story.
A lat injury wiped out most of the 2025 season, and he spent much of 2026 in the minors. Shoulder inflammation then sent him to the IL, leaving him with a year that did little to restore confidence.
For a Cubs front office that rarely dives into the top tier of the pitching market but does like betting on pitchers with a track record, Gil fits the mold.
Clarke Schmidt would be a different kind of swing. He’s still viewed as part of the Yankees’ rotation future, even after missing most of the year while rehabbing from Tommy John surgery.
But with a lost 2026 behind him and free agency looming after next season, he might not bring back a massive return. That makes him the type of short-term rotation add Chicago could consider.
Since 2022, Schmidt has put up a 3.73 ERA and 4.00 FIP over 381 innings, and before the elbow injury, he looked like he was finding his footing on the mound.
Ryan Weathers may be the most appealing arm of the bunch. He brings the kind of profile that can draw real interest if the Yankees decide to shuffle the roster and chase catching or infield help.
Weathers keeps the ball on the ground, a trait Jed Hoyer has consistently valued, and with two years of team control left, he wouldn’t come cheaply. Of the three, he’s the one most capable of moving the needle.
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