The Chicago Cubs are winning the offseason by dodging free agent bullets

The Chicago Cubs have not exactly lit the baseball world on fire this offseason. With glaring roster needs facing them ahead of the 2026 season, the team’s movement has been characteristically slow, steady, and conservative.

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So far, Cubs president Jed Hoyer and his front office have primarily focused on the bullpen, which was down to precisely two 2025 holdovers– Daniel Palencia and Ben Brown. Free agent signings of Phil Maton, Hoby Milner, Jacob Webb, and Hunter Harvey were mostly well-received, as was the re-signing of Caleb Thielbar.

There was no way around the add-ons. They, literally, had six bullpen slots to fill and not that much time in which to fill them.

The Cubs’ other needs, however, are not as immediately pressing, but it could be argued that they are more important in the big picture.

Chicago Cubs needs unfulfilled

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Chicago needs another high-end starting pitcher, preferably of the front-of-rotation variety. Their current rotation is solid, but there are a lot of durability concerns in play when three starters (Shota Imanaga, Jameson Taillon, and Cade Horton) spent significant time on the IL last season and another (Matthew Boyd) has a significant history of injury. There’s also ace Justin Steele, who will be returning from April elbow surgery at some point in the season. There’s just not a lot of security with this staff, especially when the goal is a deep playoff run.

The Cubs also need to make up for the offensive contribution lost as free agent right fielder Kyle Tucker moves on to another city.

When Tucker was in the lineup and healthy, the Cubs offense was dominant. When he was hobbled by injury or altogether absent, the offense tanked. It remains to be seen whether rookie outfielder Owen Caissie or rookie DH Moises Ballesteros can fill that gaping hole in the lineup.

As of right now, the team has addressed neither the starting pitching need nor the Tucker replacement.

Missing their marks

When it comes to starters that piqued their interest, they are currently 0-3. They were outbid by the Toronto Blue Jays for Dylan Cease. They whiffed on Michael King. They let Tatsuya Imai slip away.

On the offensive side of things, hopes of signing free agent third baseman Alex Bregman seem to be fading as more aggressive bidders emerge. On Saturday, free agent Japanese import third baseman Kazuma Okamoto came off the board as the Blue Jays gobbled up another available talent.

Potentially losing out on Bregman, especially, would be a setback. It would kind of put the kibosh on the team’s theoretical possible big-picture plan of swapping Tucker’s bat for Bregman’s and freeing up current third baseman Matt Shaw to be traded for a starter.

But, despite the doom and gloom circling Cubs fandom right now, there’s no need to worry about the North Siders failing the offseason just yet. As a matter of fact, they may have dodged some bullets by taking so many “L’s” this offseason.

Winning by losing

The 7-year contract Cease got could be seen as an agreement to throw away at least two or three full years as the hard-throwing 30-year-old righty moves well past his prime and his arm loses some of its potency. It’s already been widely noted that when Cease can’t fireball, he struggles.

King struggled through injury last season and, really, only has two years as a full-time starter. Imai, meanwhile, has never pitched in the majors before and many have legitimate doubts about his durability and long-term MLB viability.

Okamoto is an unknown entity and, realistically, even in a best-case scenario, not that much of an upgrade over Shaw at third– plus he’d cost about $14 million more than the sophomore Shaw.

So, it could be said that the Cubs may have actually won by losing these reported targets.

The big, important free agents are still out there. Bregman is still on the market. Pitchers Framber Valdez, Ranger Suarez, and Zac Gallen are still there as well. Any of the above would be game-changing, roster-fortifying additions. Even Tucker is still there for the taking. There’s also the possibility of swinging a big trade for a front-of-rotation starter.

If the Cubs get none of the above, though, and spend the rest of the offseason bargain hunting, there should be a righteous uproar from Cubs fandom.

This team is very close to contending for a championship and they have the payroll flexibility to get whoever they want. If they don’t make a major move, it means they made a conscious decision to not pay the price for next level success.

The post The Chicago Cubs are winning the offseason by dodging free agent bullets appeared first on ChiCitySports.

Source: https://www.chicitysports.com/chicago-cubs-free-agents-2026-bregman-tucker-cease-matt-shaw