The many tough decisions Yankees are facing in crucial offseason

The Yankees’ postseason lasted all of one game, leaving them far short of their goals and another year without a World Series title — or appearance. They now head into the offseason with plenty of questions after a loss on Tuesday to a Red Sox team that had been expected to be rebuilding this season.

Here’s a look at some of what the Yankees will need to address before the 2022 season — which could be delayed (or worse) depending on what happens when the Collective Bargaining Agreement expires on Dec. 1, which could lead to a lockout or strike.

Changes at the top?

General manager Brian Cashman has another year on his contract and has been the GM for nearly a quarter century. When the Yankees appeared to be free-falling out of the playoff hunt, it seemed at least possible Cashman’s job could be in jeopardy. The Yankees’ improved play in the second half with the help of trade deadline additions of Anthony Rizzo and Clay Holmes (and despite the trade deadline additions of Joey Gallo and Andrew Heaney) and appearance in the postseason would figure to secure at least another year for Cashman.

Brian Cashman (left) and Aaron Boone
Charles Wenzelberg/New York Post

Manager Aaron Boone’s future is more complicated, since his contract is up. He certainly bears some responsibility for the wild ups and downs of the regular season: a brutal start, a 13-game winning streak and then a near-collapse at the end of the regular season. It all added up to a disappointing performance before the postseason, as the Yankees were unable to come close to the Rays for the AL East title and were overmatched against the Red Sox in the wild-card game. The Yankees will have to decide whether to give Boone a new multi-year deal or look for his replacement, as well as the fate of his coaches. 

Make a splash at shortstop

Corey Seager is one big name the Yankees could pursue at shortstop this offseason.
Corey Seager is one big name the Yankees could pursue at shortstop this offseason.
AP

The Gleyber Torres experiment at shortstop has come to an end, with the 24-year-old playing much better since his move back to second base in September. The Yankees could still look to move Torres this offseason, since they wanted DJ LeMahieu to play second. This is a historic free agent class for shortstops, with Trevor Story, Corey Seager, Javier Baez, Marcus Semien and Carlos Correa all slated to hit the market. Whether the Yankees are willing to expand payroll to make room for any of those players remains to be seen. They also have prospects Anthony Volpe and Oswald Peraza in the minors.

Judge and jury

Aaron Judge is about to enter his final year of arbitration before he hits free agency. Judge said recently there have been no extension talks. That could change this offseason after Judge had his healthiest and most productive year since he was a rookie in 2017. He said Tuesday night he wanted to be a Yankee “for life.” As for the rest of the outfield, Brett Gardner has a player option for next season and said he would like to return, Aaron Hicks is expected back from wrist surgery and the Yankees will have to hope Gallo plays better than he did after his arrival from Texas. Clint Frazier’s year was sidetracked by injuries again and his future is unclear.

Catch this

Gary Sanchez wasn’t as bad as he was in 2020, but he wasn’t good enough to guarantee his return to The Bronx. He showed flashes at the plate, but struggled again for long stretches and was subpar defensively. The Yankees decided to keep him around for $6.35 million last offseason, and he will likely cost even more in arbitration next year. Still, getting rid of Sanchez is easier than finding a replacement. Kyle Higashioka is well-suited to his current backup role.

Has Gary Sanchez played his final game with the Yankees?
Has Gary Sanchez played his final game with the Yankees?
Corey Sipkin

Who’s on first?

Luke Voit’s injuries — in part — led to the trade for Rizzo, and the former Cub got off to a fast start with the Yankees before he landed on the COVID IL. He hasn’t been the same at the plate since, but he’s remained solid offensively and provides good defense. He’ll be a free agent, and with Voit suffering a season-ending knee injury last week, the Yankees will have to figure out the position. In theory, LeMahieu could play there, but that’s not why they brought him back for six years and $90 million last offseason.

Starting five

Deivi Garcia and Clarke Schmidt failed to establish themselves as major league options, so the Yankees will need to add starting pitching again. Corey Kluber could come back as a free agent. Bigger potential targets include Max Scherzer, Robbie Ray and Kevin Gausman.

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