Yankees: Five moves they should attempt to make during the Winter Meetings

Trade J.A. Happ

If the Yankees sign Gerrit Cole or add another starting pitcher this week they could look to trade J.A. Happ for a couple of reasons. The first would be to clear up some cap space. Happ is owed $17M in 2020 and has a vesting option for the same amount in 2021. If he stays with the Yanks next season he probably won’t be allowed to reach the 27 starts or 165 innings he needs to for his contract to vest but he could with another club in need of a veteran starter.

The second reason he could be dealt is to open up a spot in the starting rotation for Jordan Montgomery. The soon to be 27-year-old southpaw missed the first five months of the season last year recovering from Tommy John surgery, but he’ll be ready to go in 2020. In 2018, Montgomery had a terrific rookie season for the Yanks and still figures to be a big part of the team’s rotation for years to come.

Whether it’s Cole or someone else the Yankees are going to add another starter and if Happ remains on the roster Montgomery could be relegated to the bullpen. It’s important to have starting pitching depth but clearing up cap space and securing a spot for Montgomery on the starting staff is more important for this Yankee team. And it’s not as if they’d have a lack of depth after trading Happ because Mike King and top prospect Deivi Garcia could both crack the rotation at some point next season. (Don’t forget about Domingo German either).

Even if it means the Yanks have to attach a high-end prospect to get another team to take Happ they should still do it. Knowing their willingness to sign Cole to a record-breaking contract, they should really try to clear up some cap space and outside of trading Giancarlo Stanton (which isn’t happening) the best way to do it would be by trading Happ.