New York Yankees long-time GM Brian Cashman is looking to the trade and free agency market to improve a club that hasn’t won the World Series since 2009. (Photo by Mark Blinch/Getty Images)
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The New York Yankees fell short of winning the World Series this year for the 16th consecutive season and according to long-time general manager Brian Cashman, “have a lot of work to do and a whole winter to do it,” getting back to that place.
The Yankees have won the World Series a record 27 times, but not once since defeating the Philadelphia Phillies in 2009, the year the current Yankee Stadium opened. They haven’t suffered a sub-.500 season since 1992.
“The team we had last year, which was really good on paper but fell short of our ultimate goal, is now depleted because of free agency,” Cashman said last week in a group interview. “We’ve got to find a way to get back to at least where we were, but the ultimate goal is to make it better.”
The Yankees have to find their way in both form and substance. They finished at 94-68 tied for first place in the American League East with the Toronto Blue Jays, who pummeled them all year winning 11 of the 17 times the two teams played in the regular season and playoffs.
The Blue Jays finished first by virtue of winning their head-to-head matchup with the Yankees and ultimately went on to lose the World Series to the Los Angeles Dodgers on the final pitch of the 11th inning in Game 7.
The Jays did it with the antithesis of play to the Yankees. They are a contact hitting team constantly putting the ball in play that led the 30 Major League Baseball teams with a .265 batting average and strike out far less: a league low 1,099 times in comparison to New York’s No. 3 most 1,463.
“They guys who’ve been around here for a while, the regulars, they can hit,” Blue Jays manager John Schneider said in an interview during the World Series. “They all hit for a relatively high average, for the most part, and they all have good bat-to-bat skills.”
It would seem that Bo Bichette, a free agent shortstop, who hit .311 with 18 homers, 94 RBIs and an .840 OPS for Toronto last season, would be the guy to help change that equation for the Yankees, who desperately need a shortstop.
The Yanks currently stand at $237.5 million committed in payroll for tax purposes, second in MLB behind the two-time World Series-winning Dodgers. The luxury tax threshold for 2026 is $244 million. Thus, there’s always a question how far above the threshold the Yanks will want to spend. This past season they finished $77 million above the threshold for a $60.2 million tax bill.
The Blue Jays already have a fourth in the league $208.6 million committed for 2026.
The Yanks, who hit .251 as a team, philosophically rely on the three true outcomes: homers, strikeouts and walks. They led the league with 274 homers, but rarely won if they weren’t clouting the ball.
They’re built around Aaron Judge, the now two-time in a row AL MVP, who hit 53 homers, yes, but also led MLB with a .331 batting average, 86 points higher than the league’s .245 average and 80 points higher than his own team. Judge’s other periphery numbers were stellar, far above Seattle’s Cal Raleigh, his closest MVP challenger, who set the record with 60 homers as a catcher and switch-hitter.
“I thought Judge deserved it,” Cashman said. “But the guy in Seattle had a hell of a year.”
Aaron Judge is the key to the Yankees. A three-time American League MVP, including the last two in a row, he clearly needs some help to win the World Series. (Photo by Al Bello/Getty Images)
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It’s obvious Judge can’t do it alone as he’s finding out. The Yanks haven’t won it all during his 10-year career as the current club’s captain. Will he be Don Mattingly, who didn’t win the World Series during 14 seasons playing for the Yankee, or Derek Jeter, the previous captain who won five times in 20 seasons?
The supporting cast has a lot to do with it. At times, Jeter had Andy Pettitte, Jorge Posada, Mariano Rivera, Bernie Williams and CC Sabathia on the team with him. Jeter, Rivera, Sabathia and manager Joe Torre are all in the National Baseball Hall of Fame.
Surrounding Judge this past season, the Yanks had a catcher in Austin Wells who hit .219, a shortstop in Anthony Volpe who hit .212. a center fielder in Trent Grishman who hit .235, is a .218 career hitter and just accepted the club’s $22 million qualifying offer. Ben Rice hit .255 in a platoon at first base with Paul Goldschmidt, also now a free agent. Third baseman Ryan McMahon hit .208 after the trade deadline deal that brought him over from Colorado.
That’s not a lot of backing.
“Obviously we need to get more contact hitting,” Cashman said, stating the obvious. “We have too many Ks, especially at the bottom of the order. Our internal guys can improve in that skill or that can be corrected by importing somebody. Time will tell.”
Their next best hitter, Cody Bellinger, who batted .272 with 29 homers and 98 RBIs, declined his own player option and is now a free agent. Cashman said he’s talked to Bellinger’s agent, Scott Boras, about bringing him back. But everything with Boras is always a long process as he scours the market for the best offer.
The Yankees have also lost relievers Devin Williams and Luke Weaver, who are free agents and probably won’t be back. And starters Gerrit Cole (Tommy John surgery on his right elbow) and Carlos Rondon (left elbow surgery to remove loose particles) aren’t expected to return until May at the earliest, Cashman said.
Volpe also recently had left shoulder surgery to repair a partially torn labrum and may not be ready to start the 2026 season, leaving the door wide open for the right-handed hitting Bichette.
“It’s always pitching and pitching first and foremost,” Cashman said. “We’re left-handed [hitting] predominantly. Getting that bat from the right-handed side would be a benefit if we could make it happen.”
Right-handed hitters, third baseman Alex Bregman and first baseman Pete Alonso, are out on the market, but the Yanks don’t seem to be interested in either. Regarding Bo there hasn’t been a peep.
But as Cashman said, they have the whole offseason to figure it out.