Oakland Athletics The
Oakland Athletics drafted Naile in the 20th round, with the 608th overall selection, of the
2015 Major League Baseball draft. He split his first professional season between the rookie–level
Arizona League Athletics and Low–A
Vermont Lake Monsters. Naile split the 2016 campaign between the Single–A
Beloit Snappers, High–A
Stockton Ports, Double–A
Midland RockHounds, and Triple–A
Nashville Sounds, accumulating a 9–11 record and 3.39 ERA with 125 strikeouts across 28 games (26 starts). Following the season, Naile was named the best defensive pitcher in
Minor League Baseball. Naile split 2017 between Midland, Stockton, and the AZL Athletics, compiling a 2–3 record and 3.30 ERA with 57 strikeouts across 18 games (14 starts). He made 26 starts for Midland and Nashville in 2018, registering an 8–10 record and 4.54 ERA with 84 strikeouts across innings pitched. Naile split the 2019 season between Midland and the Triple–A
Las Vegas Aviators. In 27 games (24 starts) for the two affiliates, he compiled a 10–7 record and 5.41 ERA with 92 strikeouts over innings of work. Naile did not play in a game in 2020 due to the cancellation of the minor league season because of the
COVID-19 pandemic. He spent 2021 with Las Vegas, making 51 appearances out of the
bullpen and posting an 8–0 record and 4.04 ERA with 51 strikeouts across innings pitched. Naile elected free agency following the season on November 7, 2021.
St. Louis Cardinals On November 18, 2021, Naile signed a minor league contract with the
St. Louis Cardinals. The Cardinals promoted Naile to the major leagues for the first time on June 27, 2022. He made his MLB debut that night versus the
Miami Marlins, pitching one scoreless inning of relief. He made seven total appearances for the Cardinals in his rookie campaign, posting a 5.00 ERA with five strikeouts in nine innings pitched. On February 8, 2023, Naile was
designated for assignment by St. Louis following the acquisition of
Anthony Misiewicz. On February 10, Naile cleared waivers and was sent outright to the Triple-A
Memphis Redbirds. In 6 games with Memphis, Naile posted a 3-1 record and 2.50 ERA with 19 strikeouts. On May 5, his contract was selected to the active roster. In 10 major league contests for St. Louis, Naile struggled to an 8.80 ERA with 7 strikeouts across innings of work.
Kia Tigers On January 19, 2024, the Cardinals sold Naile's contract to the
Kia Tigers of the
KBO League. On August 24, Naile was struck in the face by a comebacker off the bat of
Matt Davidson, and later diagnosed with a fractured jaw. He was temporarily replaced by
Eric Stout. In 26 total starts for the Tigers, he compiled a 12–5 record and 2.53 ERA with 138 strikeouts across innings pitched. With Kia, Naile won the
2024 Korean Series. On November 26, 2024, Naile re–signed with the Tigers on a $1.6 million contract. He made 27 starts for Kia in 2025, compiling an 8-4 record and 2.25 ERA with 152 strikeouts across innings pitched. On November 26, 2025, Naile re-signed with the Tigers on a one-year, $1.8 million contract. ==Personal life==