The Chicago Cubs are in a frustrating position of having a number of high-paying deals that simply aren't aging in their favor. The upcoming trade deadline is a clear chance to attempt to shed at least one of these deals if there is any team willing to take a gamble on a reclamation project. As the Cubs continue to fall behind in the National League Central, there is no choice but to attempt to shed salary.
It is important to note that the trio of deals the Cubs need to attempt to deal are going to be incredibly difficult. There is a great chance none of the following players are traded, but it is a gamble the team should take, actively shopping their frustrating contracts, starting with infielder Dansby Swanson.
If Chicago becomes sellers, these veterans should be available
1. Dansby Swanson
Swanson is owed $28, $27, and $26 million each of the next three seasons. It is hard not to become incredibly frustrated with a deal that is paying an infielder who has struggled to reach the Mendoza line in the 2026 season. Still, Swanson is a World Series champion and has an impressive resume that could tempt some team into taking a gamble on the infielder as a reclamation project. Even if it is swapping bad contracts, Swanson getting a fresh start and Chicago finding a deal that expires sooner would be a win.
For Swanson, it is incredibly unlikely you're going to find a new team willing to take on your deal. However, it is completely impossible based on career accomplishments, and the shortstop should welcome the chance at a fresh start.
2. Alex Bregman
We are not one year into Bregman's deal and fans already have reason to panic around how it might age. The infielder signed a five-year deal worth $175 million and is currently hitting .246 and hasn't been the consistent source of offense expected. If there is one piece that you almost can assuredly move it is Bregman. The veteran has a respected resume and would be a potential offensive push for a World Series contender.
The Cubs have every reason to want to turn the page based around the early-season frustrations on the deal and the infielder not fitting the timeline of contention. Dealing Bregman and offloading the salary makes a great deal of sense and gives the veteran one last chance to make another meaningful postseason run.
3. Carson Kelly
The veteran catcher is a far lower deal than Swanson or Bregman, but is an aging veteran that no longer fits your timeline for meaningful contention. Next season has a $7.5 million club option, with next year offering clear value for a contending team looking for a viable backup option. The Atlanta Braves are one potential answer as the team has shuffled six catchers out of the lineup due to consistent injury issues.
No matter the landing spot, Kelly makes sense as a trade chip when you look at the veteran's current contributions. Chicago should at least explore giving Kelly a new landing spot ahead of this year's deadline.
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