Cubs Facing Tough Decisions On Key Free Agents

As the Chicago Cubs navigate a pivotal season, crucial decisions loom over which players will remain for the long haul and who might be on their way out.

The Chicago Cubs made waves after their Opening Day loss by locking in second baseman Nico Hoerner with a six-year contract extension. This move, long anticipated by fans, solidifies Hoerner's role with the team and eases the front office's offseason workload for next year.

While Hoerner's future is secure, the Cubs face big decisions with several key players hitting free agency after 2026. They can't extend everyone, so this season will be crucial for those looking to make their mark. Let's dive into the roster and see who might stay or go.

Outfielders: Ian Happ, Seiya Suzuki, Dylan Carlson, Michael Conforto

Dylan Carlson and Michael Conforto, both signed on minor league deals, earned spots on the Opening Day roster. As bench players, they'll see more action while Seiya Suzuki recovers from a knee injury. Their future with the Cubs is uncertain, as neither is positioned to make a significant impact yet.

Conforto has a better chance of sticking around if he can return to his early Mets form, hitting 25+ home runs. His playing time will depend on the health of Suzuki and Happ.

Ian Happ might be the next extension target. As the longest-tenured Cub, a four-time Gold Glove winner, and a consistent on-base threat, Happ is a cornerstone. Given the slim pickings in next year's free-agent outfield class, the Cubs might want to keep him, provided the price is right.

Seiya Suzuki presents a tougher challenge. Coming off a career year with 32 home runs and 103 RBIs, Suzuki's value is high.

With the Cubs already investing heavily this offseason, retaining Suzuki won't be cheap. If Matt Shaw proves himself in right field, Suzuki's days in Chicago might be numbered post-2026.

Starting Pitchers: Shota Imanaga, Jameson Taillon, Matthew Boyd

Expect a shake-up in the Cubs' rotation for 2027. Shota Imanaga, Jameson Taillon, and Matthew Boyd are likely on their way out. All three are over 30 and showing signs of decline.

Taillon, turning 35 next year, struggled with injuries in 2025 and had issues with home runs when healthy. Imanaga's second half of 2025 was rocky, leading to the Cubs declining his club option.

Boyd, with a $15 million club option for 2027, seems unlikely to return despite a strong 3.21 ERA last year. His postseason dip and advancing age make it hard to justify keeping him.

The Cubs still have Justin Steele, Cade Horton, and Edward Cabrera, with affordable options for Javier Assad and Colin Rea. Top prospect Jaxon Wiggins is also primed for future contributions if he stays healthy.

Letting Boyd, Taillon, and Imanaga walk frees up $57 million, giving the Cubs financial flexibility in a promising pitching market. While landing a star like Tarik Skubal might be a stretch, Freddy Peralta, Zac Gallen, and Brandon Woodruff could be viable targets.

It's tough to see Boyd, Taillon, and Imanaga go, as they've been key to recent postseason runs. But age catches up with everyone, and the Cubs are focused on building a lasting contender, highlighted by extensions for Hoerner and Pete Crow-Armstrong. A younger rotation is part of that vision.

Relief Pitchers: Hoby Milner, Caleb Thielbar, Hunter Harvey

Predicting the future of relief pitchers is tricky due to their volatility. Milner is on a one-year, $3.75 million deal.

Thielbar and Harvey have mutual options, which are rarely exercised. If they perform well, they could stick around, but Thielbar, turning 40 next year, seems the most likely to depart.

The Cubs have a knack for retooling their bullpen, so expect them to adapt as needed under Jed Hoyer's leadership.