With the main target of the 2019-2020 offseason reportedly secured, the Yankees front office now shifts their focus to rounding out the roster.
Last week, the Yankees reportedly agreed to a deal with Gerrit Cole to make him the highest paid pitcher in the history of baseball; however, the Winter Meetings weren’t all about additions for the Yankees as they lost free agents Didi Gregorious and Austin Romine who signed deals with the Phillies and Tigers, respectively. With the future still up in the air for players like Dellin Betances and J.A. Happ, it’s time to start looking at potential moves that could be made over the next couple months to best position the Yanks for a World Series run.
Re-sign Dellin Betances?
Dellin Betances had an injury riddled season to forget last year as he was only able to throw 0.2 IP before tearing his achilles to end his 2019 campaign all together. However, Dellin Betances was one of the best relievers in baseball from 2014-2018 posting a 2.22 ERA while striking out 14.6 batters per nine innings pitched. The Yankees are reportedly not in an “active dialogue” with the right-hander at the moment but rumor has it that Betances is willing to take a one-year deal to reestablish his market.
Opinion: If Betances is genuinely interested in signing a one-year deal, I think it is a no doubter the Yanks should offer him such to sure up the back end of an already dominant bullpen.
Backup Catcher?
With Austin Romine leaving the Bronx and headed to Detroit, the Yankees need to decide if they are ready to promote Kyle Higashioka to backing up Gary Sanchez full time or testing the market for a better, more experienced option. One of those potential options is Martin Maldonado who hit only .213 with 12 home runs and 27 RBI last year but caught all 10 of Gerrit Cole’s starts after Maldonado was traded from the Cubs to the Astros.

Kyle Higashioka has displayed great defense behind the dish and is notorious for pop at the Triple-A level but still hasn’t been able to translate that offensive power to the big leagues in his limited plate appearances. Sanchez has a less than ideal injury history and an even worse defensive reputation which makes it imperative for the Yankees to have a capable back up in case of emergency.
Opinion: I believe Higashioka has the ability to back up Gary full time but it is hard to overlook that connection Maldonado has formed with Gerrit Cole when he posted a 1.57 ERA with 114 strikeouts in 68 2/3 innings with Maldonado behind the dish.
Trade for Josh Hader?
According to MLB Network’s Jon Heyman, the Yankees are still in talks with the Brewers about a potential deal that would land one of the game’s best relievers, Josh Hader, in the Bronx next season. The 25-year-old lefty has an outstanding 2.52 ERA in 116 games over the past two seasons and averaged 16.1 strikeouts per nine innings; however, the Brewers still have Hader under contract for the next four years so getting him to the Bronx would cost the Yanks a King’s ransom.
Opinion: Although imagining Hader in pinstripes is an incredible visual, I think the bullpen is good enough as is (hopefully with the addition of Betances) that there isn’t a need to empty the prospect tank to get Hader in the Bronx.
Other moves I’d like to see:
- Send J.A. Happ to the moon (or back to Toronto).
- Sign DJ LeMahieu to a contract extension.
- Sign a good lefty hitter to a one-year deal.