The Chicago Cubs are in a position to win the National League Central and reach the postseason for the first time in years, and they need to be aggressive at the July 31 trade deadline.
Adding players mid-season means that some of the current roster members can’t stick around forever. There are only 26 active roster spots and these three players may not make it past the deadline with the Cubs expected to make additions.
1. Ryan Pressly
Ryan Pressly has been one of the more disappointing members of the 2025 roster. The Cubs struck a trade with the Houston Astros to acquire Pressly in the offseason with the inention that he would be the team’s closer this year.
But Pressly lost the ninth-inning job at the beginning of May after an eight-run meltdown against the San Francisco Giants. Daniel Palencia has now claimed the ninth inning, with Brad Keller, Drew Pomeranz and Caleb Thielbar getting the bulk of the work in high-leverage situations. Porter Hodge is on the injured list, but he is also expected to be another trusted arm when he returns. That means Pressly’s margin of error is shrinking as the season goes on.
The 36-year-old has been a bit better since his horrid outing, and he’s turned in eight scoreless outings in May. But he is still having trouble keeping runners off the basepaths (1.75 WHIP), and he’s given up at least a walk or hit in seven of his last eight appearances. If the Cubs bring in another setup man or trade for a closer at the deadline, there’s a good chance Pressly will be the odd man out.
2. Chris Flexen
The Cubs need to add a starting pitcher. It’s plain and simple. The team could have used another experienced starter before Justin Steele got hurt, but now that he is out for the season, the need is even more glaring. There are major concerns that some of the current pieces of the rotation could deal with burnout down the stretch, as Ben Brown and Matthew Boyd only logged around 50 innings in 2024.
Injecting a workhorse starting pitcher will give the team a third man alongside Shota Imanaga and Jameson Taillon, who have both proven they can pitch a full season’s worth of games (150+ innings). If/when that happens, Chris Flexen could be out of a job if he is still around at that time. Flexen is currently the team’s long reliever, a job that he has excelled in so far since he has a 0.00 ERA in his 14.1 innings with the Cubs.
But Colin Rea would figure to take his place in the bullpen after the Cubs trade for a starter, and he theoretically takes priority over Flexen since he is signed to a $6 million major league contract and has a club option for 2026. It would be an unfortunate scenario for Flexen, especially if he can continue pitching well. But he could also be part of a potential trade package, and he could find a new job on a different team in the final months of the season.
3. Cade Horton
Some will not like this but it’s a scenario that could become reality. Cade Horton is the Cubs’ most valuable young pitcher and opposing teams would be foolish if they didn’t ask for him if they are trading a valuable starting pitcher to the Cubs. This is especially true if the Cubs acquire a pitcher with multiple years of team control like Pablo Lopez, Sandy Alcantara, or Luis Castillo.
This would be painful since Horton has looked like a capable major league pitcher in his first four outings, where he has struck out 16 batters in 20.1 innings. But it’s hard to project how productive Horton will be come the late rmonths of the season since the 23-year-old missed more than half of the 2024 season with a shoulder injury. 2025 could be the only chance for the Cubs to make a deep playoff run and Horton may not be ready to pitch in October.
It’s not set in stone that he will be traded since the Cubs have a plethora of top prospects to bargain with. But it’s certainly possible and Horton probably won’t be on the active roster down the stretch anyway. With Imanaga and Javier Assad expected to return from injury and potentially a starter from outside the organization, Horton could finish the season in Triple-A if he’s still with the team.