Pete Crow-Armstrong could headline Cubs extension moves at Winter Meetings

The MLB offseason has been fairly active early on, but it's about to kick into high gear with the Winter Meetings beginning next Monday in Orlando. For a Chicago Cubs team looking to build on a 92-win season and divisional round playoff exit, this will be the time to act and, ideally, bolster a pitching staff in need of an ace. However, there's fair reason to believe internal moves might be on the team's radar after Jed Hoyer made it clear extensions would be explored this year.

Multiple players on the roster stand out as potential candidates, whether because they're about to reach free agency or because they simply make sense to lock down right now. At the top of that list is center fielder Pete Crow-Armstrong. Last season, the Cubs approached the budding superstar with an extension reportedly worth around $90 million, though he ultimately turned it down to bet on himself. That gamble paid off thanks to an MVP-caliber first half that ultimately ensured he ended with a 30-30 season worth 5.4 fWAR despite his struggles after the All-Star break.

Bruce Levine reported at Marquee Sports Network last month that revisiting a potential long-term deal with Crow-Armstrong will be a priority this offseason for obvious reasons. Aside from their past interest, 2025 also showed that the 23-year-old has the potential to be one of the best players in the game when hitting well, complete with the personality to be a face of the franchise. If he had an entire season combining his 131 wRC+ first-half production with his elite defense, the cost to retain him for years to come would skyrocket. It would be best to act now when he's going to potentially command a deal closer to Jackson Merrill and Corbin Carroll's more reasonable $100+ million commitments.

In theory, those talks could happen at any point from now into spring training. However, there's reason to believe the Cubs could, and should, get to talking with players and their agents in Orlando. The team has much to sort out when it comes to the team's future beyond 2026, so they may prefer to figure out potential extension possibilities before committing to longer-term free agents.

Aside from the looming MLB lockout that could have massive financial ramifications depending on the new CBA, the North Siders also have to consider the sheer number of looming free agents in 2027. Ian Happ, Seiya Suzuki, Nico Hoerner, Carson Kelly, Jameson Taillon, Shota Imanaga, and more are set to walk after the upcoming season and take a lot of money off the books. Some of those holes will be filled by younger players, ideally, but it would make sense to explore deals with at least a few outgoing players to start adding some certainty to an otherwise wide-open roster.

The Cubs have several high-priority extension candidates

Crow-Armstrong isn't on an expiring deal, but would easily command the biggest commitment that could force the Cubs to go to lengths they've mostly avoided. He'd be the highest, yet most important hurdle to overcome. After figuring out the terms of his deal, they would have a better idea of where their payroll sits after 2026 and who would be worth spending on going forward. It would make plenty of sense for Hoyer to want to get that contract nailed down first and soon.

Hoerner sticks out as a must-sign from there, coming off his best season yet by fWAR (4.8) with a .297/.345/.394/109 wRC+ slash line and another Gold Glove. His consistency throughout the season proved invaluable yet again and, behind the scenes, he stepped up as a leader in the clubhouse. After his Rookie of the Year runner-up campaign, Cade Horton would be a logical candidate as well since he was awarded a full year of service time for his performance. The Cubs haven't typically done the type of deal that involves buying out years of arbitration for a pitcher, but they could use some cost certainty in the rotation.

Even if deals aren't completed, expect the groundwork to be laid next week for something down the line this offseason. It wouldn't be shocking, though, if the Cubs wanted to get a jump on things and get their young star outfielder, or another key contributor, locked in for the long haul before their next long-term moves.