Ryan started 2019 with the Bowling Green Hot Rods and was promoted to the Charlotte Stone Crabs and Montgomery Biscuits during the season.

[8] Ryan was assigned to the Triple-A Durham Bulls to begin the 2021 season, and logged a 4–3 record and 3.63 ERA in 12 appearances, 11 of them starts.

On July 22, 2021, while Ryan was in Tokyo competing in the 2020 Summer Olympics, he was traded alongside Drew Strotman to the Minnesota Twins in exchange for Nelson Cruz and Calvin Faucher.

[9] After making 2 starts for the Triple-A St. Paul Saints, posting an ERA of 2.00 with 17 strikeouts, the Twins selected Ryan's contract when the rosters expanded.

[11] Despite missing a month due to injury, Ryan had a career year as he led the team in wins (13), strikeouts (151) and innings pitched (147).

[16] He went six innings in a group stage win against Israel, and left with a no-decision in the semifinal game against South Korea.