In 71 games with the Chicago White Sox back in 2021, speedy outfielder Billy Hamilton quickly made himself a fan favorite on the South Side.
It's hard to pin down exactly why White Sox fans fell in love with Hamilton. A .620 OPS, while well below league average, was right on par with Hamilton's career numbers. That was about all you could expect from him when he joined the White Sox as a minor league free agent.
Hamilton only stole nine (9) bases with the White Sox in 2021. His days of stealing 50+ were far behind him, but even still, White Sox fans developed a strong affection for Billy Hamilton during his time with the team that season.
The highlight reel defensive plays and clubhouse energy brought a winning spirit to Chicago as they coasted to an AL Central title.
The organization loved his energy so much that they brought Hamilton back on another minor league deal before the 2023 season. He played in three games for the Sox in May of 2023 before landing on the Injured List.
Now, Hamilton is hoping to bring the same energy and speed across town when he joins the Chicago Cubs for the playoffs.
Billy Hamilton could join the Cubs for the playoffs
The last time Billy Hamilton stepped on a field in a Major League uniform was May 4, 2023 with the White Sox.
Hamilton spent the back half of 2024 and most of 2025 in the Mexican League with Charros de Jalisco.
At the end of August, the Chicago Cubs signed Hamilton to a minor league deal, stashing him in Triple-A Iowa with hopes of adding him to the playoff roster as a defensive replacement and pinch runner.
Hamilton already has three stolen bases in four games played with the Iowa Cubs.
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
This is not an uncommon strategy for clubs that have clinched a playoff birth and are looking for an extra edge in the postseason. The Kansas City Royals are the team that really made it popular back in 2014-2015 when they won the American League pennant in back-to-back seasons.
Kansas City had speedster Jarrod Dyson in the outfield and "designated runner" Terrance Gore on the playoff roster.
Terrance Gore was also brought in by the Cubs for the same reason role in 2018. He stole a base and scored Chicago's lone run during the NL Wild Card Game.
In 2021, Gore played in the playoffs for the eventual World Series champion Atlanta Braves without ever playing a game in the regular season. That could be what we see the Cubs do with Billy Hamilton - no regular season appearances but pinch running in the NL Wild Card Series.
Because the Cubs signed him on August 31 before the deadline, Hamilton is postseason eligible.
Even though he played for the Cubs first, Billy Hamilton is a player that White Sox fans claim as their own. Unfortunately, they may have to watch him chase an elusive World Series ring with the Cubs this October.