With a postseason spot now secured, the rest of the regular season for the Chicago Cubs will be spent on preparing their roster for an October push. Players like Moises Ballesteros certainly have made a strong case to be on the postseason roster, but there is a forgotten veteran currently playing with the Iowa Cubs who could be the true difference maker.
Lost in the flurry of roster moves the Cubs made at the deadline for postseason roster eligibility, the team signed veteran outfielder Billy Hamilton to a minor-league deal. After spending a couple of weeks at the Cubs' Spring Training complex in Arizona, Hamilton has joined the I-Cubs and has provided an instant reminder of the value he could bring the Cubs in October.
The Cubs brought Billy Hamilton in to be a potential pinch run option on the postseason squad. Safe to say the legs are still there.
— Aram Leighton (@AramLeighton8) September 18, 2025
They've been pinch running him in Triple-A games to get the legs going again. 3 for 3 so far. Here's two of them on two straight pitches. pic.twitter.com/MkfDaK6CMk
Cubs quietly preparing a postseason X-factor in Triple-A
No matter the team, there almost certainly is a spot designated on the postseason roster for a player who can enter the game in the later innings and swipe a bag. There's no shortage of base stealers for the Cubs in their starting lineup with Pete Crow-Armstrong, Nico Hoerner, and Matt Shaw, but the team doesn't quite have that option currently on the bench. Hamilton almost certainly will be that piece.
A player like Hamilton is almost always the unsung hero for a team in October. The last time the Cubs were in the postseason, Hamilton was actually on their roster. The Cubs turned to the veteran during the final month of the shortened 2020 season, and he swiped 3 bags for the team in 14 games.
Depending on the status of Kyle Tucker, dealing with a calf injury, and Owen Caissie, in MLB's concussion protocol, it could be easy to slide Hamilton on the roster once the postseason starts. It would also be fair to suggest that if Tucker and Caissie are healthy and on the Cubs' postseason roster, Hamilton could replace veteran first baseman Carlos Santana on the team's bench.
