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3 difficult playoff roster questions facing the Cubs before Wild Card series

Playoff roster is starting to come into focus.
ByJordan Campbell|
Aug 21, 2025; Chicago, Illinois, USA; Chicago Cubs right fielder Kyle Tucker (30) walks back to the dugout during the fifth inning of a baseball game against the Milwaukee Brewers at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
Aug 21, 2025; Chicago, Illinois, USA; Chicago Cubs right fielder Kyle Tucker (30) walks back to the dugout during the fifth inning of a baseball game against the Milwaukee Brewers at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

The Chicago Cubs will be playing in the National League Wild Card round, but there is some uncertainty regarding who they will play and if those games will be at Wrigley Field or on the road. The focus has begun to shift to the preparation of their playoff roster, and for the Cubs, there are some important decisions.

It starts with Kyle Tucker. Tucker has been sidelined since the first week of September with a calf injury, and with each update from Craig Counsell, it feels like Tucker is closer to being out for the rest of the season than he is playing another game for the Cubs.

Will Kyle Tucker be ready for the playoffs?

The biggest decision surrounding the Cubs is the health of Tucker. Since Tucker suffered the injury, the diagnosis has gone from the All-Star outfielder being considered day-to-day to the team being hopeful he is able to play again before the playoffs. If Tucker doesn't return before Sunday, it's fair to wonder if he will be on the Cubs' roster for the Wild Card round.

If Tucker isn't available, that likely opens the door for Owen Caissie to be on the playoff roster, assuming he is cleared from concussion protocol before then.

Could Billy Hamilton slide onto the playoff roster?

It would seem that the Cubs are angling for Billy Hamilton to have a spot on the playoff roster. Hamilton signed with the Cubs at the start of September, ensuring playoff eligibility, and has lived up to his reputation during his latest stretch of games with the Iowa Cubs. Hamilton's inclusion on the playoff roster could be tied to the health of Tucker and Caissie, but chances are the speedy veteran will find a way to be with the team in October.

How will the starting rotation line up?

With his stretch of dominance during the second half of the season, Cade Horton seems to be in line to be the Cubs' Game 1 starter. Even with his struggles giving up home runs of late, Shota Imanaga feels like the safe bet to be the Game 2 starter. The real question is who will be the Game 3 starter, considering Matthew Boyd has regressed during the second half of the season. Jameson Taillon could be the option on a short leash, with Boyd potentially available out of the bullpen.

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