In 2019, Olson started 14 games for High-A Wisconsin Timber Rattlers, posting a 4–7 record with a 4.66 ERA and 84 strikeouts over 94 innings.

[1] In 2021, Olson started 14 games for High-A Wisconsin Timber Rattlers, posting a 5–4 record with a 4.30 ERA and 79 strikeouts over 69 innings.

On May 31, the Tigers announced that Olson would be promoted to the major leagues for the first time to start two days later against the Chicago White Sox.

[9] On the season, Olson made 21 appearances (18 starts) at the major league level, posting a 5–7 record with a 3.99 ERA and 103 strikeouts in 103+2⁄3 innings.

Entering the 2024 season, Olson made the Tigers' Opening Day roster as part of their rotation, beating out Matt Manning for one of the final spots.