The 2025 postseason was not kind to the Yankees and Cubs, both losing in the Division Series round. Now with their season done, both teams will be focusing on their offseason moves, one that includes Cody Bellinger and Kyle Tucker.

The Yankees must decide if they can afford to re-sign their outfielder, Cody Bellinger. Meanwhile, the Cubs face the near-certain departure of Kyle Tucker, the player they acquired for their one-year playoff push. Now, the decisions these two teams make will shape the entire free-agent market this offseason. But the verdict on Kyle Tucker‘s future in Chicago seems already given. According to Sahadev Sharma of The Athletic, the Cubs likely won’t be the team to give Tucker a massive new deal.

“The Cubs, the reality is, the Cubs do not spend like a top-five, uh, market,” Sharma said on the show Foul Territory. “They are a top-three market and they spend like a, you know, middle-tier market… I don’t think they’re going to re-sign him. I’d be surprised by it.”

Sharma believes Chicago always viewed the Tucker trade as a one-year rental. And the superstar’s injury-plagued season in Chicago, where he suffered a hairline fracture in his hand in June and then a calf strain in September, hurt his performance and likely his price tag. The Athletic’s insider added, “I don’t think he’s going to get that $400 million deal we were talking about, uh, six months ago.”

Even with a potentially lower price, the Cubs may avoid Tucker because of a long-term commitment, and that is where the Yankees enter the chat.

According to a report from Randy Miller of NJ.com, New York’s interest is real. “The Yankees love Tucker,” Miller wrote, but he quickly pointed out Tucker is “probably going to get $40 million a year for a bunch of seasons. That’s Judge money.” This is the main problem for a team already loaded with massive contracts for aging stars. So, the question remains: do the Yankees really commit that kind of cash again? Miller’s answer was clear: “Doubtful.” But the reason goes beyond just the money.

“Bellinger is better suited for the Yankees because he’s elite at all three outfield spots and first base,” Miller explained. “Tucker is a right fielder who played some left early in his career and very little center.” All the logic seems to point in one direction: re-signing Bellinger. Because he’s a more flexible defender and will probably cost way less than Tucker. But even this will not be easy because of the competition from a few potential suitors like the Mets, Phillies, and Giants.

This sets the stage for a tempting offseason

The outfield is just one of many problems the Yankees need to solve. Their 2025 season exposed several other glaring weaknesses. The shortstop position is a huge question mark, where Anthony Volpe struggled badly in his third year, hitting just .212 and leading all of baseball with 19 errors. And the front office will face an urgency to fix the problems in the infield while they’re still getting MVP-caliber seasons from Aaron Judge, who will be 34 years old next year.

The bullpen was another problem they will try to fix ASAP. Key trade acquisitions like Devin Williams and Camilo Doval failed to deliver, and the Yankees’ bullpen had one of the worst season records among all playoff teams.

Now, come to the Yankees’ own youth movement, and the front office’s future decision will show in which way they want to show the franchise in the coming years. They have high hopes for top prospects Jasson “The Martian” Domínguez and Spencer Jones. Domínguez, who showed some flashes of his talent in 2025, has a defense problem. Jones, who will be 25 years old next year, has struggled with a 35.4 percent strikeout rate in the minors that is nearly 3 percent more than the highest K percentage in the majors. Committing to a long-term deal for Bellinger or Tucker would directly block the path for these young players.

At the same time, the Cubs are at their own crossroads with an inconsistent offense that relies too heavily on home runs. Their key starters were on IL, and a majority of their effective bullpen pitchers are now free agents.

Now, the Yankees and Cubs are facing so many internal issues, the door is wide open for other teams like the Los Angeles Dodgers, New York Mets, and Philadelphia Phillies. They all have deep pockets and clear needs in their outfields.