3 Yankees the Cubs could poach if Rays sweep forces New York into an offseason reset

To the surprise of no one, without Aaron Judge, the New York Yankees are a dramatically different team. The Tampa Bay Rays boat raced Aaron Boone's club in the ALDS, sweeping their division rival and beginning the perennial tradition of speculating about Boone's future in the Bronx.

After the Game 3 loss last week, Judge set his sights on the front office and ownership, making it clear that anything less than a championship-caliber roster is a failure in his eyes. There's a lot to like about this team, but you can't rule out some offseason creativity from Brian Cashman as he looks to bring a title back to New York for the first time since 2009.

The Chicago Cubs, similarly, face a long offseason to-do list, largely centered around rebuilding a pitching staff that underperformed, battled injuries and is facing massive turnover in free agency. The two teams have gotten together on deals in the past and it's not out of the realm of possibility they do so again this winter.

3 Yankees who could be perfect Cubs trade targets this winter

Luis Gil

Just two seasons removed from his 2024 AL Rookie of the Year campaign, the shine has come off right-hander Luis Gil in a hurry. The right-hander punched out more than 10 batters per nine that year, making 29 starts and working to a 3.50 ERA in 151 2/3 innings of work.

A lat injury cost him most of the 2025 season, and he spent much of 2026 in the minors. Shoulder inflammation forced him to the IL, as well, so it was hardly a confidence-building performance. The Cubs refuse to play at the top of the pitching market, but love rolling the dice on someone who has had success in the past but is no longer viewed as a sure thing. Gil fits that bill perfectly.

Clarke Schmidt

The Yankees' embarrassment of riches in the rotation is what makes all of these names potential trade chips. Unlike Gil, Schmidt is still viewed as an important piece of the rotation's future, even after spending most of the year rehabbing from Tommy John surgery.

He shouldn't demand anything significant in return given he's coming off a lost 2026 and is a free agent after next season, and the right-hander could be a nice short-term add to a Cubs' rotation. Since 2022, Schmidt owns a 3.73 ERA and 4.00 FIP across 381 innings of work. Prior to suffering that elbow injury, he seemed to be coming into his own on the mound and the Cubs could bet on that trend continuing in 2027.

Ryan Weathers

Ryan Weathers is the most impactful arm of this group for multiple reasons and could be in high demand as the Yankees look to shake up their roster, potentially exploring catching and infield upgrades this winter.

In his first season with the Yankees, the southpaw turned in a career year, making 24 starts and working to a 3.50 ERA. He pushed 140 innings for the first time, by far a personal high, and averaged better than a strikeout per inning. A flexor strain cut his regular-season short, but he returned in the Division Series, pitching out of the bullpen against the Rays.

Weathers is great at keeping the ball on the ground, which is something we know Jed Hoyer loves in his pitchers. With two years of team control remaining, Weathers wouldn't come cheap but represents the biggest needle-mover in terms of potential Yankees trade chips.

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