Is Billy Hamilton Being Stashed for the Wild Card Round?

The Cubs will have some interesting decisions to make with their postseason roster once September 30 rolls around. First and foremost: Will they have 12 or 13 pitchers? If they opt for 12, which seems likely due to only needing three starting pitchers (at least for the Wild Card Round), they very well might add an unexpected piece to the mix on the bench.

Billy Hamilton had not played a major league game since 2023, where he played just three games for the Chicago White Sox. He spent 2024 and most of 2025 in the Mexican League. In 2024, on four different teams, Hamilton stole 80 bases, and in 2025, had seven swipes in limited playing time. There's no doubting that the speed is still there.

The Cubs saw the speed, and convinced Hamilton to come to Iowa just in time to remain postseason eligible. He isn't pretending to be a hitter; Hamilton has only stepped up to the plate twice. He has played defense and stolen bases. This would be the role the Cubs would envision for the playoffs. If, in a tight game, someone who is speed challenged laces a single, there would be Hamilton, trotting out to the bases. Really, that's the only thing he would be asked to do. 

It's a roster luxury to have a pinch runner like Hamilton. Terrance Gore played this role for the Kansas City Royals in 2015 in their championship run. He also filled the role for the Cubs in 2018 and scored their lone Wild Card Game run. Unfortunately, due to the 13-inning game, he tallied two other at bats which were both strikeouts. Gore would be the nearest comparison for Hamilton.

If the Cubs do add him for the Wild Card Round, they will have to ensure he's not at the plate in any key moments. Michael Martinez was never intended by Cleveland to bat with the World Series on the line in 2016; he was pressed into action as a defensive replacement. Hamilton absolutely cannot be placed in that situation.

It would be ideal to have, say, Kevin Alcantara in that role, or someone else who could pinch run and also hit if needed. The Cubs roster is not optimized at this point. But, Hamilton could result in an extra run every time he plays, and in any given game that can be valuable. Time will tell, but don't be surprised if Hamilton runs the bases in a crucial moment in the playoffs. He could swing a game without even swinging a bat.

The speedster's time on the roster would likely be as fast as his sprint speed, though. The Cubs will surely roster 13 pitchers for the NLDS, assuming they get that far. Hamilton would then be a fun luxury and historical footnote. And if the Cubs go all the way, Hamilton's ring will bling just as brightly.