The Biggest Questions Facing the Yankees This Offseason

All the attention is on Aaron Judge, but the Yankees have a lot of work to do this winter.

Step 1 of the Yankees’ offseason went about as expected, even if the news wasn’t popular.

Team owner Hal Steinbrenner told The Associated Press that he expects Aaron Boone to return as manager next season. That’s not a surprise after New York re-signed Boone to a three-year deal last offseason and the Yankees enjoyed a more successful campaign than they did in 2021.

Step 2 of the offseason will be locking in a general manager, though a change there would also come as a shock. Brian Cashman is on an expiring contract, but The AP reported that he and Steinbrenner were meeting in Tampa to discuss the upcoming offseason.

While New York’s leadership is unlikely to change, a busy offseason awaits after the Astros swept the Yankees in the American League Championship Series. A large swath of fans are unhappy with the organization – which hasn’t reached or won a World Series since 2009 – despite a 99-win season and an American League East title.

Houston exposed a sizeable talent gap and a flawed New York roster, which means significant moves are required on the Yankees’ part this offseason. Whether the team actually makes those moves – and follows through on its championship or bust mantra – remains to be seen, but these are the pressing questions facing New York this winter.

Will Aaron Judge return?

This is the big one after Judge put together an MVP caliber season, hit a record-setting 62 home runs, and flirted with a Triple Crown. The impending free agent practically dragged the Yankees to the playoffs, though he struggled during them.

Judge rejected a seven-year, $213.5 million extension offer from New York hours before Opening Day this year. He’s only increased his value since then. He’s stated a desire to remain with the Yankees – and vice versa – but free agency will welcome other suitors and uncertainty to the table. Yankees fans will surely be irate if New York is outbid, but Judge wouldn’t be the first superstar to leave the team that drafted and developed him.

What is New York willing to spend?

This question starts with Judge, but it also goes beyond him. In addition to potentially giving the outfielder a record-setting contract, New York has other in-house free agents and has demonstrated a serious need to upgrade the group it ran with this past season.

But the Yankees of today are not the Yankees of old. Steinbrenner has viewed the competitive balance tax as a self-imposed salary cap in recent years – though not every year – and he’s been unwilling to spend on marquee talent at times, even when the Yankees plan to exceed tax thresholds. Failing to make sizeable investments this offseason would be another way to spark outrage and increase the chances of another season falling short.

Will other veterans return?

Judge is not the only notable Yankee slated for the open market. Andrew Benintendi, Jameson Taillon, Matt Carpenter and multiple relievers are among the team’s other free agents, and Anthony Rizzo has a $16 million option. He could parlay that into a new deal that gives him more security.

Benintendi and Taillon have expressed interest in returning, but their price – and Judge’s decision – will factor into the equation.

Then there’s the matter of veterans the Yankees could try to – or should at least want to – rid themselves of. Aaron Hicks and Josh Donaldson come to mind after poor seasons, but Hicks is under contract for another three years and Donaldson is owed $21 million in 2023.

What will the bullpen look like?

Four Yankees relievers are set to become free agents, including three staples from the last several years: Aroldis Chapman, Zack Britton and Chad Green. Miguel Castro, coming off his first season with the club, is the fourth pitcher.

Chapman is surely a goner after taking an unsanctioned PTO day before the playoffs, while Green underwent Tommy John surgery in early June. Britton, meanwhile, only pitched in three games following his own Tommy John comeback this past season. However, his leadership is valued within the organization.

The Yankees will also be without Scott Effross due to Tommy John surgery, and Michael King is coming off his own season-ending injury. While he doesn’t plan on missing any time next year, there are plenty of question marks in new York's pen.

What’s the plan at shortstop?

The Yankees knew they had a problem at shortstop this time last year, yet the team used three different starters during the postseason. That’s a clear indication that Isiah Kiner-Falefa can’t man the position full-time moving forward.

The idea, upon trading for “IKF” in the backfiring deal that also netted Donaldson, was to have a stopgap for prospects Anthony Volpe and Oswald Peraza. The Yankees sparingly used Peraza after calling him up in September, instead displaying a stubborn commitment to Kiner-Falefa until their season was on the line. Assuming the Yankees pass on another talented shortstop free agent class, one of the kids should get the job. Kiner-Falefa can move to a well-suited utility role.

How much youth will the Yankees rely on?

Speaking of kids and utility roles, Oswaldo Cabrera was one of New York’s more pleasant surprises in 2022. He injected energy into the team from the moment he was called up, played excellent defense at multiple positions, and eventually showed off a big league bat. The Yankees should view his success as a lesson: show some faith in your youth.

Other youngsters who stepped up in 2022 included relievers Ron Marinaccio and Clarke Schmidt. But as previously noted, the Yankees could have turned to Peraza. It will be interesting to see if he and/or Volpe crack the Opening Day roster next year. A pitcher like Schmidt, meanwhile, could compete for a rotation spot if Taillon is not re-signed and the Yankees don’t add a starter.

MORE:

• Hal Steinbrenner Plans to Keep Aaron Boone as Yankees' Manager
• Five 2022 Yankees Elect Free Agency
• Aaron Judge Headlines Yankees’ Potential Free Agents

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