Chicago Cubs face brutal reality check in trade deadline pursuits

The Chicago Cubs, in the days leading up to the All-Star break, had a clear mission—keep their beleaguered, banged-up pitching staff at least somewhat functional until the trade deadline.

More News: Chicago Cubs encouraged to trade for one-time top prospect

By the August 3 MLB deadline, the team would restock with some much-needed pitching help. At the very least, they were expected to pick up a high-end starting pitcher and a couple of solid relievers. Many believed they would go even deeper into the market to find two viable arms for a rotation rocked by injury.

In the meantime, they would tread water as best they could with the ragtag collection of emergency fill-ins and castoffs from other teams they were forced to employ.

Maybe, though, the expected deadline haul won’t happen after all. Maybe the treading of water will have to continue for the rest of the season.

Sellers becoming buyers

Sonny Gray, Chicago White Sox — May 24, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) walks to the dugout after pitching during the third inning against the Minnesota Twins at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images

More News: Chicago Cubs: Insider targets “perfect fit” for Cubs trade deadline shopping

The thing is, back when all of these “Cubs will be aggressive buyers” stories were everywhere, the standings looked significantly different than they do right now. Specifically, some of the teams with the most attractive trade bait for the Cubs have worked themselves into being contenders.

The Boston Red Sox, for example, were expected to trade away both Sonny Gray and Aroldis Chapman. Their current 13-game winning streak, though, has given them the third AL Wild Card spot and a realistic chance of moving further up.

The Miami Marlins have surprised everyone with their 2026. They are now four games over .500 and right at the gate of NL Wild Card consideration. So, consider Sandy Alcantara and any other attractive pitching option off the table.

The Minnesota Twins, Arizona Diamondbacks, Washington Nationals, and even Detroit Tigers can probably be taken off the sellers list as well. They could even join the Red Sox and Marlins as buyers—something which would strain the trade deadline market even further.

Right off the bat, this could mean that expected stud pitchers Gray, Chapman, Alcantara, Joe Ryan, Merrill Kelly, Zac Gallen, Foster Griffin, Casey Mize, and Tarik Skubal, among others, are likely not to be traded after all.

More competition for fewer pitchers

Pat Murphy, Chicago Cubs — Apr 17, 2026; Miami, Florida, USA; Milwaukee Brewers manager Pat Murphy (49) looks on against the Miami Marlins during the eighth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images

This would also mean that there will be more competition for the remaining available arms—something that doesn’t bode well for the usually conservative Cubs, who are also lacking in tradeable high-end prospects.

To make matters worse for the Cubs, The Milwaukee Brewers—who do have plenty of tradeable high-end prospects—may now have to dive deep into the trade market for a starting pitcher. With Jacob Misiorowski and Kyle Harrison ailing and Brandon Woodruff done for the season, the NL Central rival Brewers may have no choice but to become big-time deadline buyers.

Make no mistake about it, this will be a tough market when it comes to making a deal for pitching. Whoever does pull the trigger on a big trade for a starter or elite closer will probably have to overpay greatly.

And that certainly doesn’t fit the profile of how the Cubs front office usually likes to work the trade deadline.

The post Chicago Cubs face brutal reality check in trade deadline pursuits appeared first on ChiCitySports.