He played in Major League Baseball (MLB) for the New York Yankees, Chicago White Sox, and Seattle Mariners.

[12] On November 27, 2019, Lail signed a minor league deal with the Chicago White Sox with an invite to spring training.

[21] On June 10, Lail was outrighted off of the 40-man roster and assigned to the Triple-A Lehigh Valley IronPigs without having appeared in a game for the Phillies.

[23] On April 21, 2022, Lail signed with the High Point Rockers of the Atlantic League of Professional Baseball.

[26] In total, he made 3 starts for the Rockers, compiling a 2-1 record and 0.95 ERA with 19 strikeouts across 19 innings pitched.

[27][28] He played in 16 games split between the rookie-level Florida Complex League Blue Jays, Single-A Dunedin Blue Jays, and Double-A New Hampshire Fisher Cats, struggling with a 1-3 record, 7.00 ERA, and 38 strikeouts in 36.0 innings pitched.

[29] On January 31, 2023, Lail was hired by the Philadelphia Phillies organization to serve as the pitching development coordinator their High-A affiliate, the Jersey Shore BlueClaws.