Another October, another Yankees offseason filled with questions about what needs to change. After another early postseason exit, New York can't simply run back the same roster and expect a different result.

If I had Brian Cashman's job for the winter, I wouldn't chase the biggest name at every position. I'd focus on making the Yankees harder to strike out, more dependable defensively, and better equipped to protect a lead.

Here are the five moves I'd make before Opening Day 2027.

1. Re-sign David Bednar, whatever it takes

My first priority is making sure David Bednar isn't closing games for someone else next season.

The Yankees finished 2026 with baseball's best bullpen ERA, and Bednar was a huge part of it. The two-time All-Star converted 35 of 39 saves with a 2.47 ERA, 1.04 WHIP, and 76 strikeouts in 69 1/3 innings. Since arriving from Pittsburgh at the 2025 deadline, he's posted a 2.39 ERA with 45 saves in 86 appearances.

New York could extend him a one-year, $23.15 million qualifying offer, but as one of the top relievers on the market, Bednar has every reason to pursue a multi-year deal.

And frankly, I'd give him one.

With other bullpen arms potentially leaving, creating a ninth-inning problem when the Yankees already have the solution would be senseless.

2. Replace Jazz Chisholm Jr. with a right-handed infielder

I'd let Jazz Chisholm Jr. walk in free agency and use second base to address New York's lefty-heavy lineup.

Aaron Judge remains a believer 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 does Volpe's career .662 OPS justify an everyday job? He hit .212/.272/.391 with 19 homers and a .663 OPS in 2025, then .245/.321/.336 with two homers and a .657 OPS across 70 games in 2026, including two Triple-A stints.

I'd use Volpe as a utility infielder, covering second and third, while providing insurance at short for George Lombard Jr.

Luis Arraez and Brandon Lowe, who hit 35 homers with a 121 OPS+ in 2026, are interesting options, but both bat left-handed.

One name I'd seriously consider is Mauricio Dubón. The two-time Gold Glove winner hit 12 homers with 73 RBIs, 10 steals, and posted a .720 OPS for Atlanta. He also hit .320 and .400 for Houston in the 2023 and 2024 postseasons, respectively. His right-handed contact bat and defensive versatility fit what I'd prioritize.

Miami's Otto Lopez also deserves a call. Sports Illustrated's Joseph Randazzo floated him as a trade target after a .305/.349/.437 season with 11 homers, 34 steals, and only 89 strikeouts in 687 plate appearances. Acquiring him could require moving Lombard around the infield.

Even a Gleyber Torres reunion merits consideration: injuries limited him to 96 games, but he posted a career-best .364 OBP with Detroit.

3. Add a proven outfielder

I'm not giving up on Spencer Jones, but I wouldn't hand him center field without a backup plan. The 25-year-old hit 11 homers with a .742 OPS in 86 games, yet struck out 105 times and still has room to grow defensively.

The New York Post's Joel Sherman recently reported the Yankees' previous interest in Washington's Jacob Young. The right-handed hitter batted .252 with a .708 OPS, 18 steals, and just 78 strikeouts in 140 games, plus 11 Outs Above Average in the field. He'd require a trade, with Washington controlling him through 2029.

I'd aim higher and call Cleveland about Steven Kwan. The four-time Gold Glover hit .282 with a .382 OBP and 152 hits in 2026. He's exactly the contact-oriented, defensively reliable player this roster could use.

With one year of control left, Kwan wouldn't come cheap; Cleveland might even demand Jones. I wouldn't gut the farm system for a potential one-year rental, but I'd absolutely explore the cost.

4. Add left-handed bullpen depth

Tim Hill and Ryan Yarbrough are headed to free agency, leaving Brent Headrick potentially alone among the returning lefties in the bullpen. I'd target Sean Newcomb to fill that gap.

The 33-year-old delivered a 3.09 ERA, 1.18 WHIP, and 84 strikeouts in 90 1/3 innings and 60 appearances for the White Sox in 2026. Six starts showed he can handle multiple innings, making him a practical replacement for Yarbrough. He also owns a 1.76 ERA in 15 1/3 career postseason innings.

This isn't the flashy move, but it's the kind of depth a contender needs.

5. Add a right-handed catcher behind Austin Wells

I'm keeping Austin Wells as the starter until further notice, but the Yankees need more from his backup than Ali Sánchez's .244/.275/.302 slash line and .577 OPS in 51 games.

Wells finished strong, homering four times in his final 10 regular-season games and posting a .761 postseason OPS. His defense and work with the pitching staff matter. Still, I'd give him legitimate competition.

My first call is to Ryan Jeffers. Of course, if they retained the 29-year-old who hit .256/.353/.461 with 14 homers, 56 RBIs, and an .814 OPS for Minnesota, the starter conversation would shift. The catch? He might command a non-platoon role and salary elsewhere.

Other options include Tyler Stephenson (.241, 15 homers, .727 OPS) and Carson Kelly (.258, 10 homers, .712 OPS), whose $7.5 million mutual option complicates matters.