Upcoming Roster Move Could Signal Blockbuster Trade for Cubs

Chicago Cubs left fielder Ian Happ is reportedly heading to the injured list after he fouled a ball off his left shin in Tuesday night’s 9-3 loss against the Milwaukee Brewers. It’s a bummer for Happ, who was starting to break out of his slump since he was removed from the leadoff spot. ESPN’s Jesse Rogers reported that the Cubs are calling up one of their top prospects to replace Happ on the active roster, but it’s surprisingly not one of the outfield prospects.

Cubs Calling Up Moises Ballesteros

Who knows, it could be as simple as the Cubs trusting Moises Ballesteros against MLB pitching more than Owen Caissie at this point, but seeing that the Cubs just lost one of their corner outfielders, it made sense to think Caissie could have been the one promoted. Instead, the Cubs are planning to bring up Ballesteros from Triple-A prior to Wednesday’s series finale in Milwaukee.

Ballesteros was also called up earlier this season, when Happ went on the injured list in May because of an oblique strain. The left-handed hitting prospect was 3-for-16, with two walks in five games. At Triple-A this season Ballesteros is hitting .332/.393/.496, with nine home runs in 379 plate appearances.

The 21-year-old prospect has been red-hot in July, hitting .351, with a 930 OPS across 19 games.

Owen Caissie Trade Rumors

Again, maybe the Cubs feel that Ballesteros is better suited to face MLB pitching right now, but this could have been a prime opportunity to give Owen Caissie some action. Maybe the Cubs are close to trading him?

Caissie, who the Cubs acquired in 2020 from the San Diego Padres in the Yu Darvish trade, has been in trade rumors for a while. His name was popular last winter and the Cubs were reportedly close to dealing him for Jesus Luzardo in December. That trade eventually fell through after the Cubs weren’t satisfied with the Miami Marlins’ pitcher’s medical report. Luzardo was traded to the Philadelphia Phillies and Caissie remained with the Cubs.

Now, Caissie is the No. 1 prospect in the Cubs’ minor league system according to MLB Pipeline’s rankings. The left-handed hitting outfielder got off to a slow start in 2025, but is now up to a 137 wRC+ in 82 games.

The 23-year-old outfielder has been on a tear since May 31, posting a 1.086 OPS and 172 wRC+ in his last 40 games. During that stretch Caissie has crushed 13 of his 20 home runs on the year, while slashing .320/.412/.673, in 177 plate appearances.

According to a recent report from USA Today’s Bob Nightengale, the Cubs are willing to trade Caissie for Pittsburgh Pirates starting pitcher Mitch Keller.

“The Cubs desperately want another starter at the deadline, targeting Mitch Keller of the Pirates, and would include outfield prospect Owen Caissie to make it work.”

That report was a bit surprising because Keller isn’t necessarily seen as one of the top pitchers available on the trade market. He’s been better this year, posting a 3.69 ERA in 22 starts, but the rest of his contract certainly drives Keller’s value down.

Regardless, we know that Caissie’s name is involved in trade talks. We also know that the Cubs aren’t dealing him for a rental at this year’s trade deadline, so if Caissie is departing then it’ll be for a pitcher that is under team control for multiple years.

Edward Cabrera, Sandy Alcantara, Joe Ryan and MacKenzie Gore are among the top starting pitchers the Cubs have been linked to this summer. Elite relievers such as Jhoan Duran, Cade Smith, Pete Fairbanks, Griffin Jax and David Bednar have also been connected to the Cubs in trade rumors. You can add Emmanuel Clase too, but he’s a bit tied up now.