After his sophomore season, Little was drafted by the Chicago Cubs in the first round of the 2017 MLB draft.[8][9] He signed, and was assigned to the Eugene Emeralds, where he went 0–2 with a 9.37 ERA in six starts.[10]
Little spent the 2018 season with the South Bend Cubs, compiling a 5–11 record with 5.15 ERA in 22 games (21 starts).[11] Little began 2019 with the Myrtle Beach Pelicans on the injured list.[12] After being activated from the IL, he returned to South Bend before being promoted back to Myrtle Beach. Over six starts with South Bend, he compiled a 1.91 ERA, and over four starts with the Pelicans, he went 2–1 with a 5.95 ERA.
Little did not play a minor league game in 2020 due to the cancellation of the minor league season caused by the COVID-19 pandemic. In 2021, he saw action as a reliever, pitching with the Tennessee Smokies and Iowa Cubs for the majority of the season. He found relative success in this new role, accruing a 3.24 ERA across 26 games with 53 strikeouts.
On August 30, 2022, the Cubs selected Little's contract and promoted him to the major leagues for the first time.[13] He made his MLB debut that day, pitching against the Toronto Blue Jays. On September 1, Little was removed from the 40–man roster and returned back to Triple-A Iowa.[14]
In 2023, Little spent the season with Triple–A Iowa, making 50 appearances and registering a 4.05 ERA with 73 strikeouts across 73+1⁄3 innings of work.[15]
Toronto Blue Jays
On November 6, 2023, Little was traded to the Toronto Blue Jays in exchange for cash considerations; he was subsequently added to the team's 40-man roster.[16] He was optioned to the Triple–A Buffalo Bisons to begin the 2024 season.[17]
