3 extensions the Cubs should prioritize ahead of the MLB lockout

The Chicago Cubs are hoping to make a deep playoff run with their current group, which is the most expensive in team history. But no matter what happens in October, the team will have a slew of key roster spots to replace, with five starting rotation spots, two outfield positions, and multiple bullpen jobs to fill.

The team will likely have over $100 million to play with, but the weak free-agent class and unpredictability of the looming collective bargaining agreement expiration makes this offseason a particularly difficult one to navigate. There are a handful of players that I think are no-brainers to bring back and the team should take advantage of the five-day window they have to exclusively negotiate with these players. That window begins immediately after the end of the Worlds Series, and these three players should still be Cubs when it ends five days later.

Clay Holmes

The Cubs have five starting pitchers hitting free agency this year so they will be active in the starting pitching market. They can check off one box before the lockout by offering Clay Holmes a contract after the playoffs end.

In my opinion, Holmes is a top-5 starting pitcher in this upcoming free agent class and other teams will be eager to land him since the talent pool is fairly lackluster. The Cubs should take advantage of their five-day window to negotiate with Holmes before he hits the open market and give him a competitive offer. They have money to spare and rotation spots to fill so get it done early.

Carson Kelly

Carson Kelly's two years in Chicago have been very solid. The front office brought him in on an $11.5 million contract, and he has a respectable 4.3 fWAR in those two years. Good enough for 12th best among all catchers in MLB since the start of the 2025 season.

Kelly's contract includes a mutual option for 2027 worth $7.5 million. Mutual options are almost never picked up and they normally just mean that the player will hit free agency. I could see Kelly's situation being a rare exception. His mutual option would represent a well-deserved raise worht roughly $2 million, which would also make him the 8th-highest paid catcher in baseball.

If Kelly wants a bit more money, I'd give it to him. The Cubs have roughly $140 million in payroll coming off their books this winter, so they can afford to pay Kelly a bit more if he asks for it. Reporters always remarking about how Kelly loves playing in Chicago, he's been fantastic on offense and defense, and top prospect Owen Ayers likely isn't ready to take on a starting MLB job. If Kelly rejects the mutual option, offer him something like two years for $18 million and call it a day.

Seiya Suzuki

Even worse than the starting pitching free agents is the crop of outfielders hitting the market this winter. Among them, Seiya Suzuki is by far the most talented alongside Randy Arozarena. With Ian Happ also set to leave, the corner outfield spots need to be addressed and Suzuki is the guy you want to bring back.

Behind Pete Crow-Armstrong and Alex Bregman, Suzuki is arguably the third-best hitter on the Cubs right now. He's also on pace to set career highs in doubles and OPS, and he already has in walks (75 so far). It's a double-edged sword because this makes him more valuable on the market and probably more expensive than the front office wants to pay a guy heading into his age-33 season.

But you can't let Happ and Suzuki walk away and hope to get similar offensive production from the players you have in the organization. Kevin Alcantara, Matt Shaw, or even Pedro Ramirez can't be expected to produce 25-30 home runs and 80-100 RBIs a year. With all the money the team has to play with, they can invest in pitching and also bring Suzuki back.

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