The Cubs’ trade deadline strategy has become an increasingly important conversation in 2026. Every year, you see teams part ways with top prospects to stay competitive. This often leads to lengthy lists of top trade candidates and the top needs of every organization. In turn, this prompts organizations to prepare months in advance. For Chicago, this is crucial as, despite being a top-10 team, they still have a long way to go to ensure they make the playoffs. With this in mind, examining the Cubs’ trade deadline strategy leading up to August 3rd reveals fairly clear needs.
Cubs’ Trade Deadline Needs
Top Need: Impact Starting Pitcher
One of the biggest stories of the year had been the Cubs’ injury struggles, especially in the pitching department. Nearly every starter has seen time on the injured list. In the first half of the season, the starting rotation has been one of Chicago’s biggest weaknesses. There is hope that, at some point, Ben Brown and Edward Cabrera will return, but until then, they lack a true impact starting pitcher. Even with Cabrera, it is hard to feel confident in any of the current options as a high-quality playoff game starter.
Chicago has a ton of potential in their rotation, but the first half of the season was far from great. If Shota Imanaga and Matthew Boyd return to their high-quality form, then it may not be as crucial as it seems right now. However, it just feels like it is asking too much to count on going right in that scenario. A top-of-the-rotation guy would be great, but at this point, the Cubs’ trade deadline strategy needs to bring in an above-average arm who can stay healthy.
Secondary Need: High Leverage Arm
The bullpen has had nearly the same story for Chicago in the first half. Closer Daniel Palencia has been limited to just 16.2 innings, and top setup man Hoby Milner is still a while away from a return. Beyond these two, the bullpen has seen most arms deal with injuries at some point in the season, leading to a bunch of guys being signed mid-season and thrown into high-leverage situations. They have not been awful in every game, but it still is a glaring concern.
Luckily, the Cubs have had a few guys, like Trent Thornton, Ryan Rolison, and Jacob Webb, step up and provide quality play. Despite this, it is hard to feel comfortable with them playing like that for the entire second half/postseason. Similar to starting pitching, if they can get healthy, then it could end up being alright. However, getting at least one high-leverage arm would be ideal, just to ensure that the bullpen does not revert to where it currently is.
Something to Keep an Eye on: Utility Man
One minor thing that could be in the Cubs’ trade deadline plans is adding another bench bat. Matt Shaw has been struggling with injuries lately, and once you get past him, it seems like Chicago has issues trusting any of the bench bats. Led by Michael Conforto, who has been the main off-the-bench bat, there are a few solid options. However, they are all young and unproven. Pedro Ramírez is really the only backup infielder they have, meaning if a starter gets hurt, they could be in trouble.
Now, the reason that this is just something to keep an eye on is that the Cubs’ offense is heating up. They have plenty of talent and guys who are capable of rotating around the field as needed. Additionally, if Shaw can stay healthy, then he gives them a valuable utility man who can play anywhere. Although if the Cubs did decide to trade him for a pitcher, like it has been rumored, then bringing in another guy to fill his role may be a wise decision. As long as Shaw is on the roster, I would be surprised by an aggressive offensive addition, but it remains a possibility.
Two Possible Trade Partners
Boston Red Sox
A few weeks ago, this likely would have been a lot easier to say. Sonny Gray and Aroldis Chapman would both fill exactly what Chicago needs. However, the lack of quality teams in the A.L., combined with Boston’s nine-game win streak, has put them right back in the playoff picture. That makes it hard to say that they will sell at the deadline, but for the sake of the Cubs’ trade deadline plans, we’ll say that they do. This is exactly where Shaw rumors started to grow, as the Cubs could look to include him in a package deal to acquire both of the pitchers.
Gray should have been an All-Star, with an 11-1 record and a 2.54 ERA. He could slot as one of the Cubs’ top starters and a potential game one playoff starter. Chapman, who many Cubs fans are very familiar with, is still playing at an elite level and adds much-needed velocity to the bullpen, making it a perfect trade destination for him. It would likely be expensive to get both of these guys, but even just one of them could help solidify Chicago’s pitching staff. With that being said, the Red Sox are certainly a team to monitor as we inch closer to the trade deadline.
New York Mets
The Cubs have already traded for a Mets pitcher when they acquired David Peterson in an effort to stabilize the rotation. As New York is gearing towards the future, another trade possibility is Freddy Peralta. Due to his connection with Craig Counsell when they were on the Brewers, he has been a Cubs trade target for much of the season. He has had a down year and should not cost as much as other options. Additionally, it is hard to say what teams may be selling this year, meaning that anyone in need of a pitcher, which is almost everybody, needs to jump on the opportunity.
Like the Red Sox, the Mets also have a reliever option for the Cubs. Luke Weaver has had a strong year, with a 1.85 ERA in 39 innings. The righty could slot in as one of the team’s top relievers, filling a much-needed hole. Now, the fact that he is under contract next season could make him a bit more expensive than Peralta. It remains to be seen how aggressive Chicago will be, but the Mets are a team that needs to at least be in the Cubs’ trade deadline plans to improve their pitching staff.
Last Word on the Cubs Trade Deadline
If Chicago wishes to compete in a strong National League, then improving the roster is a must. With the talent that they have, it is not wise to sit back and watch everyone else boost their chances. This is not saying to purge the farm system, but the team needs to be willing to take risks. The Red Sox and Mets are just a few of the teams to watch with them, but it could be worth it to call around with most of the league to see who is available. The Cubs’ trade deadline must be an active one if Chicago actually wishes to make a deep playoff run in 2026.
Main Image Credit: Vincent Carchietta-Imagn Images
