The idea of the Chicago Cubs becoming sellers isn't exactly far-fetched at this point. The team enters its appearance on Sunday Night Baseball 6 1/2 back in the division, clinging onto the final wild card berth in the National League.
Earlier in the year, after wrapping up a pair of 10-game win streaks, Chicago was widely viewed as a legitimate World Series contender. Now, nobody seems too sure what this team is - and there are a ton of pieces on expiring deals who could be moved if things go from bad to worse and Jed Hoyer is forced to punt on 2026.
You know the names: Matthew Boyd, Shota Imanaga, Ian Happ, Seiya Suzuki. Now, in the case of Happ and Suzuki, both have full no-trade protection and, in the case of the latter, he hasn't really done anything to make himself a hot commodity. But outside of this group, there are pieces the Cubs could move that might come as a surprise.
3 names to keep an eye on if the Cubs decide to sell at the deadline
Carson Kelly
OK, technically, Carson Kelly isn't on an expiring deal. His contract contains a mutual option for 2027 but, given how well he's played during his time with the Cubs, he's a strong candidate to go out and get another multi-year deal in free agency.
Jettisoning your primary catcher mid-season would be a heck of a move from Hoyer, but if you're looking past 2026, you need to know what you have with a potential Miguel Amaya + Moises Ballesteros tandem behind the dish. There are always contenders looking for catching help for the stretch run and his impressive 4.5 bWAR and 116 OPS+ over the last two seasons could make him an intriguing trade piece.
Jacob Webb
The next two names on this list might be surprising because they've pitched well - and in the case of Jacob Webb, he's very affordable with a $2.5 million team option for 2027.
But given Hoyer's ability to pick up pieces off the scrap heap and put together a bullpen, moving Webb, who owns a 2.27 ERA and 10.7 K/9 in 27 appearances, could help the team pick up a long-term asset and/or address some other needs. He's not going to net you top prospects or anything like that, but there's a world where a team comes calling on the right-hander, who turns 33 in August.
Hoby Milner
Funky lefty on a one-year deal? Yeah, this is a movable piece. Hoby Milner has been quite good this year, but his numbers took a major hit Friday when he allowed six earned runs and recorded just one out. Prior to that, he carried a 2.28 ERA in 27 2/3 innings of work and was effective against both left and right-handed hitters.
Given the emergence of Ryan Rolison and Caleb Thielbar's presence, the Cubs could trade Milner and still have some left-handed depth. Again, the return won't be earth-shattering, but as we saw in the Andrew Chafin trade that netted Daniel Palencia, that doesn't mean there can't be long-term value coming back.
