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] On June 1, 2024, the Blue Jays selected Little's contract, adding him to their active roster when Jordan Romano was placed on the 15-day injured list due to inflammation in his right elbow.[18] In the 2024 season, Little posted a 1–2 record with a 3.74 ERA while striking out 36 batters in 452⁄3 innings.
On October 27, 2025, Little surrendered the game-winning home run in the bottom of the 18th inning of Game 3 of the 2025 World Series to the Los Angeles Dodgers’ Freddie Freeman.[19]
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