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What’s left for the Yankees to do this winter?

It’s only December 14 and already this offseason has been more exciting than the last two combined. Here’s a quick summary of the Yankees moves so far as it pertains to the 40-man roster.


  • Gerrit Cole, 9 years
  • Brett Gardner, 1 year with an option


  • Didi Gregorius signed with the Phillies
  • Austin Romine signed with the Tigers
  • Edwin Encarnacion is a free agent, the Yankees will not resigning him
  • Greg Bird designated for assignment, elected free agency
  • Jacoby Ellsbury released, he and the Yankees will duke it out on the legal battle field
  • Nestor Cortes Jr. was traded to Seattle for bonus pool money
  • Tyler Lyons was released and is a free agent


  • Dellin Betances

There’s honestly not much left to do. The Yankees 26-man roster (yes, it’s a 26-man roster next season) is all but set. The 40-man will have some changes, but honestly most people don’t care about that.

The Rotation

The rotation will include Cole, Severino, Paxton, Tanaka, and Happ. There is news that the Yankees are shopping Happ to off-load some of his $17M salary for 2020, but for the time being, he’s here.

Jordan Montgomery and Domingo German are also rotation options, but both have questions for different reasons. Monty returned late last year from Tommy John Surgery and German ended last season serving a suspension. His status is still up in the air. We’ve seen other teams dump players with similar off-field issues as German – that’s how the Yankees got Aroldis Chapman from the Reds for pennies on the dollar – but it would surprise me if the Yankees give up German for low-level prospects.

Cole addressed the Yankees #1 need. In recent seasons Cashman addressed the rotation via trade (Gray, Happ, Paxton). This winter he ponied-up the cash for the best guy on the market. With a hopefully healthy Severino, the Yankees now have a formidable top-4 starters with some depth behind them.

If the Yankees can successfully unload Happ it would be to a team looking for veteran rotation help. Here’s a trade idea:

Lamet is a 27-year old right handed pitcher in the first year of arbitration with a $1.7M projected salary. He’s been through TJS already and has rotation and/or bullpen upside. In 73 innings last season he struck out 105 and had a 3.91 FIP. So, why would San Diego give up a guy like that?

The Padres rotation is young and inexperienced. Happ at $8.5M would provide veteran experience. Happ was terrible in 2019, but on a National League team in a big ballpark, his fly-ball approach will play better. What San Diego is really getting however is Clint Frazier and the young prospect Osiel Rodriguez. The Padres outfield stunk in 2019 – they produced a whopping 2.3 WAR. Frazier is a young piece they can stick into the OF and know he’ll hit. Rodriguez is the Yankees #28 prospect. He signed as an international FA in 2018 and utilizes a lot of pitches and arm slots.

Oh, San Diego also signed Larry Rothschild this winter so there is experience with Happ (although, now that I think about it that might not be a good thing).

The Bullpen

Like the rotation, the pen is mostly set with Chapman, Britton, Green, Kahnle, and Ottavino. Other arms will include Luis Cessa, who is also a candidate to start, and Ben Heller, Stephen Tarpley, etc., who will ride the Scranton Shuttle.

Betances is still a free agent and reportedly willing to take a one-year “prove me” contract. I know the Yankees are up against the top luxury tax threshold with the signings of Cole and Gardner, but I’d love to see Dellin back in the Bronx. At this point I don’t see it happening.

It was floated that the Yankees have made contact with the Brewers about Josh Hader, but that will cost a hefty sum of prospects. Hader is pure filth and would make the Yankees bullpen downright unfair, but honestly I’d rather just spend money on Betances, who can be just as filthy as Hader.

The Infield

With Didi on his way down the turnpike to Philly, the infield outlook is clear. Gleyber will shift to shortstop, LeMahieu will play second base, and Urshela and Andujar will battle for hot corner duties. Gio is also a candidate to move around the infield if needed, as we saw DJ do last season.

For the fifth season in a row, first base is the real question. I believe Luke Voit’s slump in the second half of last year was injury related, so the job is his at the moment. Mike Ford is another good offensive option, and his lefty bat makes for a nice platoon with Voit. The problem with both is defense. I just hope for a little stability at first base in 2020.


Backup catcher is an area the Yankees could make an acquisition. Yesterday I wrote why there are fair questions about Kyle Higashioka replacing Romine as backup catcher. If the Yankees deem Higgy too risky, they could sign Martin Maldonado, who was Cole’s personal catcher in Houston.

The Outfield

Believe it or not, I’m a little concerned about the Yankees outfield. Obviously Judge (ever heard of him?) is the anchor of the team, but he, Stanton, and Hicks have all dealt with serious injuries over the past few years. On paper the outfield is stacked: Judge, Stanton, Gardner, Tauchman and Hicks when he returns, but they all have question marks. I have no clue what the Yankees are doing with Frazier, who can’t seem to get out of his own way. Regardless, no more moves will be made in the outfield.


Players you’ll see contribute in addition to the 26-man roster the Yankees leave Tampa with are: Tyler Wade and Thario Estrada for bench depth and Mike King, Albert Abreu, Chance Adams, and Brooks Kriske for pitching depth.

A name to keep an eye on for the second half is Deivi Garcia, the Yankees #1 pitching prospect.