It is important to note that Rosenthal says there is currently “no momentum” towards a deal and there may never be. The two teams have spoken though, making such a trade worthy of some discussion.
The Cubs still hope to contend in 2020 but are also looking for some financial flexibility moving forward. The possible trades of both Schwarber and Kris Bryant, the latter connected by some to the Phillies, would offer help. Someone with a high ceiling like Miguel Andujar would make a cheap replacement to fill the hole left by Bryant.
The Yankees have reportedly been seeking a left-handed bat this winter to balance a righty dominated lineup. Schwarber hit 38 home runs last season and 29 in 2017, when the Yankees requested him in the trade for Aroldis Chapman. The Yankees would eventually “settle” for Gleyber Torres being the centerpiece of the deal.
Unfortunately, I do not believe he solves anything but the “lefty bat” issue and creates more problems moving forward. Once the calendar turns to June or July, the return of Aaron Hicks gives us a team with both outfield punch and defense. Then there is Giancarlo Stanton and Mike Tauchman, the former who is going to play every day even if only because of his contract. Schwarber’s subpar defense in left isn’t a fit.
DH would be a possibility but he is again blocked by Stanton most days. Gardner-Hicks-Judge is the best outfield placement we have, putting Stanton at DH more often than not.
First base has been mentioned as an offensive upgrade even if you are bullish on both Voit and Ford. However, Schwarber has never played the position and would become a huge defensive liability, at least in the short-term until he learns the position.