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LAS VEGAS — As the Yankees general manager since 1998, Brian Cashman is supposed to lead. He is not used to following. But in terms of keeping the superstar right fielder Aaron Judge, who is free to sign with whichever team he desires for the first time in his career, Cashman suggested he would be doing more following.
“Optimally, if you could wave a magic wand, we would secure Aaron Judge and retain him and have him signed and happy and in the fold as soon as possible,” Cashman said on Tuesday at Major League Baseball’s annual general managers’ meetings, held this year in Las Vegas. “But he’s a free agent. He’s earned the right to be a free agent. So he’ll dictate the dance steps.”
After claiming the American League East with 99 regular-season wins but losing — again — to the Houston Astros in the playoffs, the Yankees have several holes on their roster to fill. Asked for the Yankees’ needs this winter, Cashman rattled off a few areas.
“We don’t have a right fielder,” he said. “We don’t have a left fielder. I’d always like to improve the pitching. We have some kids pushing in on the infield, so there’ll be, I would think, probably a lot of exciting opportunities that could play out next spring in the middle infield.”
The right fielder vacancy was created by Judge, 30. The left fielder vacancy was created by Aaron Hicks — with $29.5 million owed over the next three seasons — struggling this year and Andrew Benintendi — acquired before the Aug. 2 trade deadline — becoming a free agent.
The Yankees’ rotation is in solid shape with the returning foursome of ace Gerrit Cole, Nestor Cortes (a breakout All-Star), Luis Severino (whose $15 million club option for 2023 was picked up) and Frankie Montas (who struggled on the mound and with a shoulder injury after arriving in an Aug. 1 trade). As Cashman said, though, the Yankees could always use more help there and in the bullpen, which has several players eligible for free agency (Aroldis Chapman, Zack Britton and Chad Green) and others likely to miss a chunk of next season (Scott Effross and Michael King).
(By the way, the presumptive A.L. Cy Young Award winner Justin Verlander, whom the Yankees have had interest in before; Carlos Rodón, an All-Star with the San Francisco Giants last season; and Jacob deGrom, the Mets’ star and two-time National League Cy Young Award winner, headline a stellar class of free-agent starters.)
The young players Cashman referred to were the rookie infielders Oswaldo Cabrera and Oswald Peraza as well as the Yankees’ top prospect, Anthony Volpe, all of whom are natural shortstops. After the Yankees’ final game of the postseason, second baseman Gleyber Torres — who has regressed in some ways in recent years — and shortstop Isiah Kiner-Falefa, who played above average defense but then sputtered and was benched in the playoffs — sounded unsure if the Yankees would bring them back next season.
With star shortstops available this winter like Trea Turner, Carlos Correa, Xander Bogaerts and Dansby Swanson, Cashman said the Yankees already had people who could handle the position (Kiner-Falefa) and others who are pushing for a chance to (Peraza, Cabrera and Volpe).
“We’re going to be open minded,” Cashman said. “There could be a lot of conversations that lead us down paths that we wouldn’t have expected. I’m not saying we would trade any of our kids. Just depends how things play out.”
Cashman did explicitly state a desire to re-sign first baseman Anthony Rizzo, who exercised the opt-out clause in his contract that had one year and $16 million remaining but was extended the standard qualifying offer of $19.65 million. Rizzo’s strong defense and left-handed power bat fit well in a Yankees’ lineup that was largely made up of right-handed hitters.
In the regular season, the Yankees led the major leagues with 254 home runs and had a strikeout rate of nearly 23 percent, the 16th best mark in M.L.B. and an improvement from recent seasons.
To cut down on this, the Yankees made a concerted effort to retain infielder DJ LeMahieu, trade for and re-sign Rizzo and trade for Benintendi. But still, during the A.L. Championship Series in which the Yankees were swept by the Astros, they struck out 50 times compared with the Astros’ 25.
Cashman pointed to the Yankees being without LeMahieu (who is still considering surgery on his injured foot) and Benintendi (hand injury) — two players who ranked in the top 25 in M.L.B. in lowest strikeout rate — as a reason for the team’s struggles against the Astros’ talented pitching staff. He said improving that in 2023 was “definitely a point of emphasis.”
He added later: “It’s an area of weakness. We’ve certainly struck out way too much in the postseason. But it’s also a byproduct of losing some people that would have prevented that if they were healthy.”
Cashman himself was operating at the G.M. meetings without a contract. His previous five-year deal expired on Oct. 31. But he continued on the job because he said Hal Steinbrenner, the Yankees’ managing general partner, expressed an interest and intent in keeping him, and Cashman wanted to stay.
The reason a new deal wasn’t completed, Cashman said, was that he had “some bigger things that need to be taken care of,” like re-signing coaches, scouts and other front office members, and navigating the Yankees through the free-agent market and the Judge courtship. “Work first, contract second,” Cashman said about himself.
But, of course, the identity of Judge’s next major-league home will be a dominant theme this winter across baseball and most acutely in the Bronx.
In spring training, Judge turned down a contract extension that would have guaranteed him $213.5 million over seven years. He also declined to negotiate during the season. That bet paid off: After several injuries in previous seasons, Judge played in 157 of the Yankees’ 162 regular-season games, produced one of the best offensive seasons in history, put himself in prime position to win the A.L. Most Valuable Player Award (which will be announced next week), smashed an A.L. record 62 home runs, played strong defense and was a team leader.
Cashman said he didn’t have a 2023 payroll figure from Steinbrenner yet and called it “a developing story” because the “right field situation will tell us a lot, too.”
In 2022, the Yankees had a $259 million payroll, the third-largest in M.L.B. As of Tuesday, they had a projected payroll of $204 million in 2023, according to Cot’s Baseball. Re-signing Judge may take a huge or record-breaking contract. And until they determine whether they can keep Judge, the Yankees’ winter plans — and backup options — will have to wait.
Cashman said the industry typically got out of the starting gate in “a tortoise like fashion.” Although he pointed to the Mets’ five-year, $102 million pact to retain their star closer Edwin Díaz the day after the World Series ended on Saturday as proof that quick deals can be done if both sides are willing. Cashman said he theoretically still had time to get a better feel for the trade and free-agent markets.
Asked what he cannot do as he awaits more clarity on Judge’s free agency, Cashman said: “I can’t sign a right fielder, right, that’s not Aaron Judge? I’m not going to do that in the near term.”