He played collegiate summer baseball for the Traverse City Pit Spitters in the Northwoods League.
[2] He did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.
In 36 appearances in 2023 with South Bend, the Double–A Tennessee Smokies and Triple–A Iowa Cubs, Little accumulated a 5–2 record and 2.12 ERA with 105 strikeouts in 63+2⁄3 innings pitched.
[4] Upon making the majors, the 6'8" Little tied the record with Chris Volstad from the 2012 season for being the tallest starting pitcher in Chicago Cubs history.
[6] On April 3, 2024, Little made his first start, throwing one strikeout with no earned runs in one inning a win against the Colorado Rockies.