As of now, it would seem the Chicago Cubs are moving forward with Matt Shaw and Pedro Ramirez having semi-regular roles in the outfield next season. It's early, and a lot can change between now and the start of the 2027 season, but such a plan would be a mistake.
The biggest reason is that both Shaw and Ramirez have had their struggles against right-handed pitching. The Cubs had one of the best offenses in baseball during the 2026 season, and could be faced with losing Seiya Suzuki and Ian Happ. Even with the need the Cubs have for pitching, that would be a drastic step back for the offense that should be avoided.
There's also the insurance that both provide for the infield. If Shaw and Ramirez are viewed as starting outfielders next season, that puts the Cubs in a dangerous position of lack of depth, considering there's no telling that Nico Hoerner, Alex Bregman, and Dansby Swanson would be healthy for the entire 2027. The Cubs will need one of Shaw or Ramirez, likely the latter, to be available to take over in the infield in the event of an injury.
JJ Bleday could be an under-the-radar trade target for the Cubs this offseason
Given those realities, it would seem likely that the Cubs add at least one outfielder. The free-agent market isn't exactly rich with options. At least, not with options that would likely fall within the Cubs' price range, considering most of the financial resources will be geared towards pitching.
The trade market could be where the Cubs turn to in their search for an outfielder, and that could lead them to a division rival. Outfielder JJ Bleday was surprisingly among the players the Cincinnati Reds didn't trade at the deadline. The Reds had a curious deadline, considering they were largely inactive despite numerous teams having interest in players like Bleday and catcher Tyler Stephenson.
In Bleday's case, he's under control through the 2028 season, and he did have a resurgent year with the Reds after struggling with the Athletics in 2025. It's possible the Reds value Bleday's presence and would like to keep him around. Though, with the threat of a shortened season in 2027, an offseason trade would make some level of sense.
Bleday would be an ideal platoon partner with Shaw or Ramirez in the outfield, considering he thrives against right-handed pitching. He hit 18 home runs against righties with the Reds while posting a wRC+ of 114. At the very least, Bleday would help replace the power the Cubs are losing in Suzuki and Happ potentially departing.
He also wouldn't be an expensive trade for the Cubs to pull off. The added year of control does add to his value, but given that his ceiling is that of a platoon player, it would seem that a deal could be centered around multiple low-level prospects from Chicago's system.
