Another October has left the Yankees staring at the same kind of winter problems they’ve been trying to outrun. After another early playoff exit, there’s no clean path forward in New York except change, and plenty of it.
If Brian Cashman is drawing up the plan, the smartest version of this offseason isn’t about chasing the loudest headline. It’s about trimming strikeouts, tightening the defense, and making sure the club can actually lock down a lead when it matters. With that in mind, here are five moves that would shape the Yankees heading into Opening Day 2027.
The first one starts in the ninth inning, where the Yankees should do everything possible to keep David Bednar from pitching somewhere else next year. New York ended 2026 with baseball’s best bullpen ERA, and Bednar was a major reason why.
The two-time All-Star turned in 35 saves in 39 chances with a 2.47 ERA, 1.04 WHIP, and 76 strikeouts over 69 1/3 innings. Since the Yankees landed him from Pittsburgh at the 2025 deadline, he’s logged a 2.39 ERA with 45 saves across 86 appearances.
The club can extend a one-year, $23.15 million qualifying offer, but with Bednar positioned as one of the top relievers available, a multi-year deal is the likelier pull for him. If other bullpen pieces leave, creating a closer problem when New York already has the answer would be hard to justify.
Second base is where the lineup decision gets more complicated. The move here would be letting Jazz Chisholm Jr. walk in free agency and using the position to balance out a left-handed-heavy offense.
Aaron Judge still sees something in Anthony Volpe, telling MLB’s Bryan Hoch, "If we were going to win a World Series, we needed Anthony Volpe on the team." But the production hasn’t matched the belief.
Volpe carries a career .662 OPS, hit .212/.272/.391 with 19 homers and a .663 OPS in 2025, then followed with a .245/.321/.336 line, two homers, and a .657 OPS in 70 games in 2026, including two Triple-A stints. The more practical role might be as a utility infielder, handling second and third while also giving the Yankees insurance at shortstop for George Lombard Jr.
If the Yankees want a right-handed contact bat with real defensive value, Mauricio Dubón is a name worth serious attention. The two-time Gold Glove winner posted 12 homers, 73 RBIs, 10 steals, and a .720 OPS for Atlanta in 2026.
He also hit .320 and .400 in the 2023 and 2024 postseason runs for Houston, which is exactly the kind of contact profile and versatility New York could use. Otto Lopez belongs in the discussion too.
Sports Illustrated’s Joseph Randazzo identified him as a trade target after a .305/.349/.437 season with 11 homers, 34 steals, and only 89 strikeouts in 687 plate appearances. Bringing him in might mean moving Lombard around the infield.
Even a Gleyber Torres reunion isn’t off the table, especially after injuries limited him to 96 games while he still managed a career-best .364 OBP for Detroit.
The outfield picture has its own question mark, and it centers on Spencer Jones. The Yankees aren’t abandoning him, but they also shouldn’t hand him center field without another option in place.
In 86 games, the 25-year-old hit 11 homers and put up a .742 OPS, but he also struck out 105 times and still needs more polish defensively. New York has already shown interest in Washington’s Jacob Young, according to the New York Post’s Joel Sherman.
Young hit .252 with a .708 OPS, 18 steals, and 78 strikeouts in 140 games, while also posting 11 Outs Above Average in the field. He would have to be acquired in a trade, and Washington controls him through 2029.
If the Yankees want the better fit, though, Steven Kwan should be the bigger swing. Cleveland’s four-time Gold Glover hit .282 with a .382 OBP and 152 hits in 2026, and his contact skills and defense line up neatly with what this roster lacks.
He wouldn’t come cheap with only one year of control left, and Cleveland might ask for Jones. Still, it’s a conversation worth having.
On the pitching side, the Yankees also need another left-hander in the bullpen. Tim Hill and Ryan Yarbrough are both headed for free agency, and that could leave Brent Headrick as the lone returning lefty.
Sean Newcomb fits the role. The 33-year-old put together a 3.09 ERA, 1.18 WHIP, and 84 strikeouts in 90 1/3 innings over 60 appearances for the White Sox in 2026, and his six starts showed he can cover multiple innings if needed.
He also owns a 1.76 ERA in 15 1/3 career postseason innings. It’s not the flashy addition, but it checks a box a contender can’t ignore.
Behind the plate, Austin Wells still looks like the starter for now, but the Yankees need more from the backup spot than what Ali Sánchez provided. Sánchez hit just .244/.275/.302 with a .577 OPS in 51 games.
Wells did finish strongly, homering four times over his final 10 regular-season games and posting a .761 postseason OPS. His defense and his work with the pitching staff still matter.
Even so, New York should push for real competition. Ryan Jeffers would be the first call; if the Yankees could land the 29-year-old, who hit .256/.353/.461 with 14 homers, 56 RBIs, and an .814 OPS for Minnesota, the whole catcher situation would change.
The catch is that he might not be available for a platoon role, and his price could reflect that. Tyler Stephenson, who hit .241 with 15 homers and a .727 OPS, is another option, as is Carson Kelly, who hit .258 with 10 homers and a .712 OPS and also carries a $7.5 million mutual option.
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