Yankees: Five free agents they should pursue this offseason

4. Didi Gregorius

One of the most interesting questions surrounding the Yankees this offseason is whether or not they will bring back shortstop Didi Gregorius. Didi is officially a free agent for the first time in his career after the Yanks declined his $17.8M qualifying offer earlier this month. After declining him the QO it might seem like the Yanks have closed the book on re-signing their shortstop of the past five years, but it’s still too early to tell.

Didi rushed himself back after undergoing Tommy John surgery last October to rejoin the team in June and that probably played a role in his poor play for most of the season. In 89 games he struggled to produce consistently and finished the year hitting .238 with 16 HR and 61 RBI and a career-worst .276 OBP. In the playoffs, he had an outstanding ALDS against the Twins hitting .400 with a home run and six RBI but he faltered in the ALCS against the Astros, hitting .213 with 0 RBI.

Due to his struggles, the Yankees clearly didn’t think Didi was worth a $17.8M salary next season and were afraid he would accept the qualifying offer. That would’ve given him an opportuntiy to rebuild his value and hit the free-agent market again next offseason. It would have been a smart route to go for Didi but he could still do that and return on a one-year deal, albeit for less money. A multi-year deal offer from New York, however, might be unlikely, especially after a down year.

The soon to be 30-year old has become expendable with Miguel Andujar and Gio Urshela returning and the ladder coming off of a career year. If the Yankees let him go they could easily shift Gleyber Torres over to shortstop and make DJ LeMahieu the starting second basemen. However, that’s somewhat concerning to me because Gleyber’s a much better defender at second and their lineup would then be even more right-handed heavy. Right now the current roster only features one left-handed hitter in Mike Tauchman that projects to be an option to start next season. Aaron Hicks is out recovering from Tommy John surgery and Brett Gardner is also a free agent, although again, the expectation is he’ll be back.

This past October showed how vulnerable the Yankees right-handed power hitters are against righty pitchers so adding another left-handed bat should be a priority this winter. Unless Brian Cashman can execute a trade there aren’t  really any free-agent left-handed hitters available that are better than Didi and in 2020 I’d bank on him having a nice bounce-back season at the plate.

The likelihood of him bouncing back and his lefty bat providing more balance to the lineup are two of the main reasons why I’d love to see Didi back. That’s in addition to him being a fan favorite and one of the top veteran leaders in the clubhouse. That might not factor into the front office’s decision to bring him back or not but it should. Didi has been a great Yankee over the past five seasons and a reunion with him for one more season still makes sense and would greatly benefit both him and the team.