The Chicago Cubs front office faces a peculiar situation this winter. Rumor has it that they want their star outfielder Kyle Tucker to sign somewhere else, and they want it to happen quickly. It sounds counterintuitive at first — after all, the Cubs traded significant prospects to Houston to bring Tucker to Wrigleyville just last season — but understanding the Cubs’ reasoning reveals a calculated strategy about finances, roster flexibility, and the reality of competing in today’s baseball landscape.
When Cubs President of Baseball Operations Jed Hoyer swung the trade for Tucker last December, sending Cam Smith, Hayden Wesneski, and Isaac Paredes to the Astros, the goal was clear, transform the offense and make a World Series run. Tucker delivered in 2025, hitting .266 with an .377 on-base percentage across 136 games, contributing 22 home runs and 25 stolen bases to a Cubs team that reached the NLDS. But with his free agency pending and him declining the qualifying offer, the Cubs have made peace with the likelihood that this was always going to be a one-year partnership.
The central issue is money. Tucker is commanding a massive payday this winter — some projections suggest a 10-year, $401 million deal. What the Cubs really need is for Tucker to get those offers from teams with deeper pockets for injured goods — the Yankees, Dodgers, and Blue Jays are all circling — and sign one of them quickly. Here’s why timing matters so much: every week Tucker remains unsigned creates uncertainty in the Cubs’ offseason planning. The front office can’t confidently allocate resources elsewhere until they know whether Tucker is returning or heading to free agency. Once Tucker signs elsewhere, the Cubs can pivot to their actual plans with full clarity and competitive urgency.
And those plans are fascinating, particularly because they might involve reuniting with two former Cubs: Kyle Schwarber and Cody Bellinger. These wouldn’t be random targets — they represent calculated solutions to the roster void Tucker’s departure would create.
Schwarber, who played for Chicago from 2015 to 2020 before departing as a free agent, has positioned himself as one of the premier hitters in the free agent class. Playing designated hitter for the Phillies in 2025, he blasted a career-high 56 home runs with 132 RBIs, setting the National League ablaze with his power. ESPN projects Schwarber will command around five years and $145 million. At 33 years old, Schwarber might seem like an expensive consolation prize compared to a younger star like Tucker, but here’s the thing: the Cubs can actually afford him. His contract would be shorter and his salary considerably more reasonable than what Tucker’s going to get elsewhere.
The challenge? Bridge-building. Some observers noted that the Cubs non-tendered Schwarber after the 2020 season, essentially telling him he wasn’t worth $8 million in arbitration. That kind of rejection stings for competitive players, and the relationship might be fractured. But offseason negotiations have a way of healing old wounds, especially when both sides benefit from the arrangement.
Then there’s Cody Bellinger. Here’s where the situation gets really interesting. The Cubs traded Bellinger to the Yankees last December for essentially nothing — just pitcher Cody Poteet and cash. It was a move designed to clear salary and space, executed almost immediately after acquiring Tucker because the front office didn’t want to pay both massive outfield contracts simultaneously. Now, with Tucker leaving for what is expected to be a massive 10-year deal they have the salary space to bring Bellinger back.
Bellinger opted out of his $25 million player option with the Yankees and entered free agency in hopes of securing a six-year, $165 million deal. While he had a solid 2025 season in the Bronx — hitting .272 with 29 home runs — he’s far from a can’t-miss superstar at age 30. Yet he’s also exactly the type of depth piece that could help the Cubs rebuild their lineup.
What’s particularly intriguing is that Bellinger’s wife reportedly has Chicago connections and was unhappy about the trade. Cubs insider Bruce Levine hinted that a potential reunion could be appealing to the family off the field. His agent, Scott Boras, told reporters that Bellinger wants to play on a winning team, which technically describes the Cubs’ 2025 NLDS run. That cryptic statement might be interpreted differently on whether you think the Cubs are winning enough right now, but it leaves the door open.
Cubs GM Jed Hoyer acknowledged that the front office isn’t treating the offensive market with the same urgency as the pitching market. Will we look to move things around? Will we look to add? Of course, Hoyer said, But the level of urgency is not nearly as high as on the pitching side” (https://mlb.com). The Cubs made the NLDS without Tucker, so the front office clearly believes they can compete without any of these outfielders. But they can also upgrade intelligently if the market cooperates.
Here’s the thing, folks: In an ideal world, Tucker signs a massive deal with the Yankees or Dodgers by early December. Schwarber returns home and reunites with the franchise that launched his career. Bellinger potentially follows, giving the Cubs a complementary outfield piece at a more reasonable cost than Tucker. The rotation and bullpen get fortified. Chicago contends for a division title instead of a wild-card spot.
With that… Cubs fans should be quietly hoping that Tucker’s agent finds him the deal of a lifetime — elsewhere. Because when Tucker leaves, the Cubs’ real offseason finally begins.
If you cannot play with them, then root for them!