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4 Cubs who shouldn't feel safe with 2026 trade deadline quickly approaching

There's a number of directions the Chicago Cubs can take.
Jun 29, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Shota Imanaga (18) celebrates after ending the top of the sixth inning against the San Diego Padres at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
Jun 29, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Shota Imanaga (18) celebrates after ending the top of the sixth inning against the San Diego Padres at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images | IMAGN IMAGES via Reuters Connect

If the Chicago Cubs series against the St. Louis Cardinals over the weekend proved anything, it's that Jed Hoyer and Co. still need to approach the MLB trade deadline with an open mind.

Current circumstances certainly still point to the Cubs being buyers. They established another safety net, approaching ten games above .500, and are firmly in the National League Wild Card conversation.

4 Cubs who aren't as safe as they think with 2026 trade deadline a month away

That said, as Cubs fans have seen this season, things can change quickly. If they do, the conversation at the deadline will have a different tune for the front office. As the Cubs map out out their path to the deadline, some players shouldn't feel as safe as they do.

Shota Imanaga

If the Cubs are buyers at the deadline, there isn't a scenario where they trade from their pitching staff at the big-league level. Injuries wouldn't allow for such a move. But if the wheels once again fall off the track, the Cubs likely will have some selling conversations.

Shota Imanaga will be included in those talks. After his struggles at the end of the 2025 season, Imanaga has been about what anyone should have expected this season. He's had some starts where he's looked excellent, and others that have been a disaster. Still, given the nature of the league, there certainly would be a taker if he were to become available. To emphasize, though, that scenario only exists if the Cubs are exclusively selling at the deadline.

Matt Shaw

Matt Shaw remains a conundrum for the Chicago Cubs. It would seem that he has a clear path toward becoming a starting outfielder for the Cubs next season, but he's also one of their biggest trade chips.

First and foremost, Shaw needs to get healthy. He's dealing with a wrist sprain, and not expected back until after the All-Star break. Beyond that, in terms of Shaw's positioning as a trade chip, it likely will be based on how successful the month of July is for the Cubs.

If the Cubs stack wins this month and the Milwaukee Brewers remain in sight within the division, it stands to reason that Shaw would be involved in some trade talks. A trade shouldn't be viewed as a likely, but it's certainly not off the table.

Pedro Ramirez

Pedro Ramirez likely has a higher chance of being trade than Shaw does. It's been limited opportunities, only 59 plate appearances, but Ramirez hasn't looked overmatched at the big-league level.

Unlike Shaw, there isn't a clear path to Ramirez having an expanded role with the Cubs after this season. As the Cubs look for controllable pitching, Ramirez likely isn't on solid ground with the team moving forward.

Kevin Alcantara

The biggest surprise at the deadline may be if Kevin Alcantara is still with the Cubs on August 4. The impression is that the Cubs have soured on Alcantara, and that seems clear with how they've handled him over the past year.

Alcantara is currently with the Cubs as Shaw recovers from a wrist sprain, but it doesn't seem like he's long for the roster. It also is pretty obvious the Cubs don't view Alcantara as a replacement for Ian Happ or Seiya Suzuki next year. The next step is going to be a trade.

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