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3 surprising players who could steal a Cubs' playoff roster spot during the Wild Card round

Keep an eye out for these Cubs making the team's playoff roster
ByRich Eberwein
Apr 7, 2025; Chicago, Illinois, USA;  Chicago Cubs pitcher Justin Steele (35) delivers against the Texas Rangers during the first inning at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
Apr 7, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Justin Steele (35) delivers against the Texas Rangers during the first inning at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

Playoff baseball usually has a way of forcing a few unexpected twists, something the Chicago Cubs have experienced their fair share of during the regular season. While the Cubs' lineup and starting rotation are mostly set, the fringe spots of the roster could see the team add a few unexpected names into the fold.

The team is looking to do anything it can to push past the National League Division Series so we could see some out-of-the-box thinking. Here are three candidates who could end up stealing a coveted spot on the playoff roster.

Here are the players who could sneak onto the Cubs' playoff roster

Justin Steele

Although the Cubs bullpen has had its moments in September, having Justin Steele back in some capacity could help stabilize things. Steele looked sharp in his last rehab outing with the Iowa Cubs, where he tossed two scoreless innings and struck out five batters.

It would be a risky play since Steele hasn't made an MLB appearance in 17 months and forcing him into high-leverage innings during the playoffs may increase his risk of re-injury. We've already seen the Cubs rule Shelby Miller out of a 2026 return for the same reasons. But the precarious state of the Cubs' bullpen could force the team's hand in pursuit of reliable relief pitching.

Justin Dean

Justin Dean grabbed a cup of coffee with the Cubs earlier this season and only appeared in 17 games before getting sent back to Triple-A Iowa. He's a depth outfielder who plays serviceable defense and has a mediocre bat (.213/.326/.297 slash line over 87 Triple-A games).

But the Cubs primarily used Dean as a pinch runner in MLB, and he has 264 career stolen bases in the minor leagues. With the team's position -player depth in a great place, they can afford to roster Dean instead of someone who is more expendable like Gabriel Arias. Runs are hard to come by in the playoffs, so having a dedicated speedster to pinch-run in big spots could be the difference between advancing in the playoffs or getting eliminated.

Gavin Hollowell

Gavin Hollowell has been working to return from a shoulder injury since July 31, and the Cubs could really use his swing-and-miss. Before going down, Hollowell posted a 21% strikeout rate across 14.1 innings pitched with a 2.51 ERA. The 28-year-old has also only allowed one earned run in his four rehab appearances with Triple-A since September 5.

If he's healthy, the Cubs could consider rostering him instead of a long reliever like Colin Rea, who has not been able to carve out a high-leverage role for himself since transferring to the bullpen. With the Cubs only needing three starting pitchers in the Wild Card round, it could be more beneficial to roster Hollowell to maximize the team's ability to get late-game outs.

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