With 12 pitchers sidelined, Chicago targets a blockbuster deal with Boston to land a few veterans.
All eyes will be on what the Chicago Cubs do to upgrade their pitching staff at this year's trade deadline.
The Cubs desperately need to acquire a top-of-the-line starting pitcher and multiple high-leverage relievers. With 12 pitchers currently on the injured list, it’s imperative that the front office addresses these two needs ahead of the August 3rd trade deadline.
Well, what better way to address these needs than by killing two birds with one stone?
There’s a team that could help the Cubs land both a premier starting pitcher and an elite closer in the same deal. That team is the Boston Red Sox.
Boston could look to deal both Sonny Gray and Aroldis Chapman next month. Gray will be a free agent at the end of the 2026 season, while Chapman likely won’t be a free agent until after the 2027 season, assuming he pitches 40 innings this year.
If the Red Sox are open to trading both pitchers at the deadline, the Cubs could be looking to do some business with them.
Gray is in the midst of a strong pitching campaign in his 14th Major League season. He is 10-1 with a 2.61 ERA, 1.104 WHIP, and 82 strikeouts across 89 ⅔ innings pitched. The veteran right-hander has a 2.03 ERA since the beginning of May and would instantly boost this Cubs’ rotation.
As for Chapman, he would give the North Siders a dominant closer for the ninth inning. The hard-throwing southpaw has a 2.36 ERA, a 1.275 WHIP, and 35 strikeouts across 26 ⅔ innings pitched. He also ranks tied for third in the American League in saves at 18.
Acquiring both pitchers in the same deal would be sweet for the Cubs. But what would a deal look like for a starting pitcher on an expiring deal and a closer who might not be a free agent until after next year?
Thomas Nestico of TJStats provided an inside look at what it might cost the Cubs to land both pitchers at the deadline.
Cubs Receive: Sonny Gray & Aroldis Chapman
Red Sox Receive: Pedro Ramirez, Jordan Wicks, Brooks Caple
This is definitely an interesting deal, and one the Cubs would consider. Although the front office would be giving up on two young players (Ramirez and Wicks) and a top-12 prospect (Caple), this is a deal that makes a lot of sense for Chicago.
Ramirez no doubt has the skill set to be a really good hitter in his career. The 22-year-old has shown glimpses of that early in his MLB career, as he is slashing .250/.283/.393 with one home run, three doubles, one triple, and seven RBI in his first 25 games.
But there is simply nowhere for him to play in the infield in the near future. Alex Bregman is signed through the 2030 season, Nico Hoerner is signed through the 2031 season, and Dansby Swanson is signed through the 2029 season.
With Ramirez being blocked in the infield for the next couple of seasons, the Cubs could look to deal the up-and-coming hitter to give them a better chance to win in 2026.
Wicks isn’t a huge loss and could benefit from a change of scenery. He has allowed 12 earned runs across 10 ⅓ innings pitched (10.45 ERA) in the majors this season and has a 7.40 ERA across 12 starts with Triple-A Iowa as well.
The biggest loss in this deal could actually be Caple. He is the Cubs’ No. 2 pitching prospect in the system and has taken a massive step forward in 2026. The 23-year-old has a 3.23 ERA, 1.08 WHIP, and 26.2% strikeout rate in 61 ⅓ innings pitched at High-A and Double-A this season.
Chicago already doesn’t have many valuable pitching prospects down in the minors, so getting rid of Caple would sting a bit.
However, this is a move the Cubs should be looking to make. Gray and Chapman would upgrade both their rotation and bullpen in one move, and this isn't a big return for two top pitchers.
