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Chicago Cubs: Odd roster move explained after team waives veteran reliever

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Hoby Milner, Chicago Cubs

The Chicago Cubs made a head-scratching bullpen-related roster move on Friday, amid some very real concerns that the bullpen in place now is quickly starting to fall apart.

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The team activated left-handed reliever Hoby Milner from the IL and then immediately placed him on waivers. Initial erroneous reporting had the team designating the 35-year-old for assignment, but that report was later corrected.

This means that Milner, who was signed by the Cubs in the offseason on a one-year $3.75 million contract to be an anchor in a rebuilt bullpen, is officially up for grabs and can be claimed by any of the remaining major league teams. If claimed, Milner is gone. If unclaimed, he’ll be back in the Cubs’ control and the team would be free to move him around the playing board as needed, whether that involves a temporary move down to Triple-A or keeping him at the big league level.

If a team picks him up, they’ll be on the hook for the remainder of his 2026 contract—which reportedly amounts to about $800K.

A puzzling move

Hoby Milner, Chicago Cubs
Jun 19, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Hoby Milner (41) pitches against the Toronto Blue Jays during the ninth inning at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images

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The updated and corrected report doesn’t make the Milner move significantly less puzzling.

The veteran southpaw has a history of being a very solid, dependable middle-relief option and it’s quite possible that at least a team or two with playoff aspirations would want him—even with him just coming off the IL and with a good amount of money owed to him for this homestretch of the regular season.

If claimed, the Cubs lose a legitimate asset who could’ve restored some stability to a stressed and strained bullpen. Before being placed on the IL on June 27, following an emergency appendectomy, the ten-year veteran had posted a 3.53 ERA through 38 games and 35.2 innings pitched.

A high-stakes gamble

Chicago Cubs, Cubs News, Hoby Milner
Jun 12, 2026; San Francisco, California, USA; Chicago Cubs relief pitcher Hoby Milner (41) throws against the San Francisco Giants during the seventh inning at Oracle Park. Mandatory Credit: John Hefti-Imagn Images

Chicago is likely gambling that other teams will pass on him, lacking roster spots at this point in the season and unwilling to add to their payrolls.

If unclaimed, the Cubs would then have added flexibility when it comes to where they can keep him and would be free to move him up and down between the big league and minor league squads to boost roster flexibility ahead of the September 1 roster expansion.

However, if the pitcher does clear waivers and the team wants to send him down to the minors, he’d also have the right to nix the assignment and declare himself a free agent.

This Milner move is certainly a gamble.

As he entered his rehab assignment in Iowa, the thought was that Milner would step back into the Cubs bullpen to replace the struggling Caleb Thielbar as the chief lefty in relief. Friday’s waiver decision casts some real doubt on that and could make for a scenario where the team walks into the postseason with the untested Ryan Rolison and Thielbar as the only dedicated left-handed relief options in the pen.

Chicago will know by the end of this weekend whether their roster gamble has paid off.

The post Chicago Cubs: Odd roster move explained after team waives veteran reliever appeared first on ChiCitySports.

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