Even with Aaron Judge signed, Yankees still trying to catch up to Astros

With the not-so-small matter of retaining Aaron Judge out of the way, what’s next on the to-do list for the Yankees this offseason?

Plenty.

General manager Brian Cashman departed the annual winter meetings last Wednesday afternoon bleary-eyed. That was the result of, in his words, not getting “any sleep” the night before. With managing general partner Hal Steinbrenner riding shotgun, Cashman worked into the early-morning hours Wednesday securing Judge with a nine-year, $360 million contract.

“That might be the first Hal-acting-like-George moment we’ve had in quite some time,” said one staffer, a reference to the late George Steinbrenner, who rarely let a player he truly wanted get away because of dollars. “Question is now: How will we navigate the rest of the roster?”

(Steinbrenner certainly channeled his far more famous — and bombastic — father just three years earlier when he refused to let Gerrit Cole end up anywhere other than the Bronx by giving the ace righthander a nine-year, $324 million deal.)

Regardless, back to the club insider’s question: How will Cashman and his baseball operations crew navigate the rest of the offseason when it comes to the roster?

As of now, though it's a good one that is more than capable of contending for a second straight AL East title as is, the Yankees roster as of now — and it is important to stress the “as of now'' element of that — does not match up with the Astros’.

"We got beat by a better team right now, and that's the reality of it," Aaron Boone said shortly after his club’s ALCS Game 4  loss to the Astros, who swept the Yankees and went on to win the World Series. "They're clearly setting the mark in this league that we're aspiring to get to."

That is the case even with Justin Verlander, an October tormentor of the Yankees more than a few times in his career, leaving Houston for Queens last week on a free-agent deal.  

Though bringing back Judge — and first baseman Anthony Rizzo before that — were important moves for 2023, more is needed to put the Yankees in the class of Houston, which not only has a deeper, more dynamic pitching staff but a deeper, more dynamic lineup.  

The Yankees still have a bevy of holes, starting with the fact that they currently don’t have a true leftfielder on the roster. Re-signing Andrew Benintendi is an organizational priority. However, there is a lot of competition in the marketplace for Benintendi's services and the Yankees, who traded for him before last season's trade deadline, could find themselves priced out.

Pirates outfielder Bryan Reynolds, in whom the Yankees showed interest  before ultimately pulling the trigger on the deal with the Royals for Benintendi, again is a consideration for a possible trade. Oswaldo Cabrera, a natural infielder who took to both corner outfield spots when the Yankees needed him to play unfamiliar positions in 2022, is unlikely to be the Opening Day starter in leftfield, though he likely will make the roster.

The Yankees like the front of their rotation — Gerrit Cole, Nestor Cortes, Luis Severino and Frankie Montas — but remain interested in bolstering the group with a big name, with lefthander Carlos Rodon currently the club’s top choice in that department. Righthander Tommy Kahnle was signed for bullpen depth last week, but another arm for that group can’t be ruled out.

Among the selling points Steinbrenner and Cashman gave Judge was that the Yankees’ offseason didn’t begin and end with him.

“We have plenty of ability to, and Aaron and I talked about this, to make this happen [sign Judge] and still have money to make other things happen,'' Steinbrenner said at last month’s owners’ meetings, referring to an end-of-season in-person conversation he had with Judge.

Those other things have yet to occur, but some of the groundwork for them has taken place, and there’s a long way to go between now and February’s report date for spring training.

As Cashman said shortly before leaving this year’s winter meetings: “We’re on the clock to continue to find ways to improve the club, both small and large. We’ll see where it takes us.”