The Cubs’ offseason picture is already starting to sharpen, and the latest buzz points to a team that may have to choose its battles. Recent reporting has suggested Chicago could be priced out of keeping both Carson Kelly and Seiya Suzuki, a sign that the front office may need to point most of its money and prospect capital toward pitching.
That’s the big takeaway here: the Cubs would love to keep the lineup intact, but the reality of the pitching staff after this season could make that a luxury they can’t afford. Kelly is projected to be one of the better catchers on the market, while Suzuki might be the top bat available.
Both are clearly worthy of new contracts. But if Chicago is going to stay disciplined, the spending priorities may have to shift elsewhere.
Two pending free agents stand out as realistic targets for another deal.
Matthew Boyd belongs near the top of that list. He gave the Cubs nearly 180 innings last year, though injuries have cut into his workload this season and likely will leave him around 100 regular-season innings.
Boyd is 35, but there’s still enough left in the tank for Chicago to move quickly if it wants him back. In a perfect world, the Cubs probably would like to retain two arms from the group that also includes Kevin Gausman, David Peterson, Clay Holmes and Shota Imanaga.
Boyd feels like the first name they should chase.
Holmes is another strong candidate. Compared with Gausman, the Cubs may prefer Holmes as a possible return piece next season.
He has a $12 million player option for 2027, but if he stays healthy and performs at the level he’s capable of, reaching free agency seems like the more likely path. Before the trade to Chicago, Holmes had interest in signing an extension with the Mets, and it wouldn’t be surprising if a similar feeling develops with the Cubs.
On the other side of the ledger, there are a couple of free agents Chicago should be ready to let walk.
Ian Happ could still return if his market gets squeezed, perhaps because of a qualifying offer, and a team-friendly agreement is not out of the question. Even so, he shouldn’t be treated as a priority. The Cubs would be better off finding his replacement in free agency, ideally someone who can hold things down until Josiah Hartshorn and Ethan Conrad are ready.
Colin Rea also fits the “move on” category, despite how valuable he’s been. He’s been the unsung hero of the pitching staff over the last two years, and Chicago does hold a $7.5 million club option for 2027.
But banking on health is always risky, as the Cubs learned this season. Javier Assad looks ready to step into that Swiss role on the staff, and he should come at a cheaper price.
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Cubs Pitching Picture For October Just Got More Interesting
Justin Steeles path back keeps the Cubs October plans from feeling static. The left-hander is still working through the recovery phase from a flexor strain, but he could be headed for a minor-league rehab assignment by the end of August, which at least puts a late-season return on the board. Chicago has been careful with its pitching timeline all year, and Steeles eventual availability would matter not just for the regular season, but for the shape of the staff once the games get bigger.
Ben Brown adds another layer to the picture after resuming bullpen work following a neck injury, with the Cubs expecting him back in a relief role before the season ends. The broader postseason forecast also looks a little more crowded, with Edward Cabrera, Hunter Harvey and Shelby Miller all projected to give the club more depth if it gets into October. For a staff that has had to manage uncertainty, that kind of incoming help could make the final month feel a lot different than the middle part of the summer. [Read more 🡒]
Matt Shaws Return Leaves The Cubs With A Tough Lineup Call
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Pedro Ramrez has earned a longer look, Tyrone Taylor brings a fresh layer to the roster after arriving recently, and Shaws reentry will test how flexible the Cubs can be as the postseason nears. Counsell will have to manage those pieces carefully, because the challenge is no longer simply getting Shaw back healthy. It is finding a way to do it without unsettling the rhythm the team has built while he was out. [Read more 🡒]
Cubs Already Have A Looming Ian Happ And Seiya Suzuki Decision
The Cubs have already started to think past the current shape of their outfield, because the end of the 2026 season could bring a real crossroads. Seiya Suzuki and Ian Happ are both lined up to hit free agency then, and while Happ could be the cleaner fit for a return on a more manageable deal, Suzuki is headed toward the kind of market that forces a club to make hard choices about its payroll and long-term roster plan.
Chicago does not appear likely to enter next winter with only one answer ready, either. The organization has been weighing younger options for the years beyond 2026, and the list of possible successors includes Kevin Alcantara, Pedro Ramirez and Matt Shaw, a reminder that this is as much about timing and development as it is about name recognition. For a front office trying to keep the window open, the next outfield chapter may be decided well before those contracts actually expire. [Read more 🡒]