The Cubs’ offseason checklist has a few moving parts, but the early decisions mostly point in one direction. Before the calendar flips to December 1, Chicago has a round of option calls to make, and most of them feel pretty cut and dry.
On the mutual-option side, the Cubs are carrying four players into 2027: Matthew Boyd at $15 million, Carson Kelly at $7.5 million, Caleb Thielbar at $6 million and Hunter Harvey at $8 million. Mutual options rarely get exercised, and they usually function as a way to push money down the road while both sides expect the player to reach free agency. That’s the likely outcome here as well.
The club-option group is smaller, and it may be even simpler. Colin Rea has a $7.5 million club option, Javier Assad checks in at $3.3 million, and Jacob Webb is attached to a $2.5 million club option.
Rea’s recent move to mop-up duty makes it feel likely the Cubs will pass on that one. Webb’s price tag looks like an easy keep for Jed Hoyer and company.
Assad is the one real judgment call, since the Cubs could decline the option and still tender him a contract for 2027 depending on his arbitration projection. Even then, he remains under team control through 2028.
The most important name in all of this is Clay Holmes. He’s the only Cub with a player option for 2027, and if he stays healthy and keeps pitching the way he has in the rotation, the $12 million figure seems like a formality to turn down. That would send him into free agency, where he could wind up as the best starting pitcher available not named Tarik Skubal.
That’s exactly why the Cubs need to be ready. If free agency gets moving fast before a possible lockout on December 1, as happened the last time the CBA expired, Holmes should be near the top of Chicago’s list. He fits the rotation, he fits the defense behind him, and with the Cubs’ need for pitching, he would be a straightforward way to stabilize the staff.
In Other News...
Cubs Fans Have Another Reason To Revisit The Kyle Tucker Trade
Hayden Wesneski has given Cubs fans one more reason to keep looking back at the Kyle Tucker deal, and not just because Tucker never spent long in Chicago. The right-hander, included in the trade package sent to Houston, has looked much more like a dependable starter after working his way back from Tommy John surgery, and his early run with the Astros has been enough to make the return package feel more complicated than it did at the time.
Through his first seven starts this season, Wesneski has paired a 3.18 ERA with a much cleaner home-run profile than he showed with the Cubs. For Chicago, that only adds to the familiar debate over whether the price for Tucker was too steep for a player who ended up contributing mostly in one season, especially if one of the pieces going the other way is beginning to settle in elsewhere. [Read more 🡒]
Cubs May Already Know Which Productive Veterans Wont Be Back
As the Cubs keep one eye on the pennant race and another on what comes next, a few expiring contracts are already shaping the winter conversation. Matthew Boyd had provided useful innings before his late-season performance tailed off, while Carson Kelly gave the club a strong return behind the plate. Tyrone Taylor, meanwhile, has been productive in a limited role and has fit in well enough to merit a look beyond the box score.
The problem for Chicago is that usefulness does not always line up with the market. Kellys price may climb beyond what the Cubs want to commit, and Taylors role could be squeezed by the roster plans already taking shape, even after an impressive stretch. Boyds uneven finish adds another layer of uncertainty, leaving the front office with several veterans who have helped in different ways but may not all be back when the offseason decisions finally come due. [Read more 🡒]
Cubs Seem Ready To Reverse A Javier Assad Decision
Javier Assad is back with the Cubs and eligible to be recalled from Triple-A Iowa ahead of the weekend series against the Marlins, a sign the club may be ready to revisit a pitching decision it made earlier in the year. Chicago still has not announced its starters for Saturday or Sunday, and Assads presence around the team puts him squarely in the mix if the Cubs decide they need another arm to bridge the stretch in front of them.
Jacob Webb and Tyler Ferguson are also part of the roster conversation as the Cubs sort through possible pitcher moves, though nothing has been made official. For a team trying to line up its rotation with a series in Miami, the timing matters, and Assads availability gives Chicago another option while it weighs how to reshape the staff for the weekend. [Read more 🡒]