Cubs' 2027 option decisions look straightforward but Clay Holmes needs to be priority

Chances are there will be a flurry of activity for teams leading up to December 1 this offseason. The first month of the offseason represents one final opportunity for teams to act within the rule that currently exist. There are also some procedural moves that will happen, and for the Chicago Cubs, their early housecleaning will be tied toward their 2027 option decisions.

The Cubs have four players with a mutual option for the 2027 season. Starting pitcher Matthew Boyd's mutual option carries a $15 million number, Carson Kelly's mutual option is worth $7.5 million, and Caleb Thielbar's is at $6 million. Hunter Harvey also has a mutual option worth $8 million.

More times than not, mutual options are never picked up. It's a classic way of deferring money owed to a player, but there's almost always an expectation that said player will reach free agency. That likely is case for all of the Cubs players with mutual options for the 2027 season.

The Cubs have three players with a club option for next season. Colin Rea has a $7.5 million club option, Javier Assad has a $3.3 million club option, and Jacob Webb has a $2.5 million club option. Considering Rea has been relegated to mop-up duty over the past week, it feels likely that the Cubs will decline his option. On the side of the coin, picking up Webb's $2.5 million option feels like no-brainer for Jed Hoyer and Co.

Assad's case is tricky. Depending on his arbitration projection, it's possible the Cubs decline the option while tendering Assad a contract for the 2027 season. Regardless, he's under team control through the 2028 season.

Clay Holmes will likely test free agency, but the Cubs need to make him a priority

Only one Cubs player holds a player option for the 2027 season and that Clay Holmes. Assuming health and Holmes continues to shine in the starting rotation, it feels like a formality that he will decline the $12 million option and test free agency. As things currently stand, Holmes could be the best starting pitcher on the free-agent market not named Tarik Skubal.

It would be fair to wonder if there will be a blitz of free agency signings before the potential lockout on December 1. That was the case the last time the CBA expired, and if so, the Cubs should make Holmes the priority. He's a natural fit in their rotation, considering the defense that is behind him. Given the need for pitching the Cubs will have, Holmes would be an easy way for them to check the box of stabilizing their starting rotation.

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