He did not sign and played college baseball at Illinois State University, where he started pitching as a redshirt junior after having primarily been a third baseman before that.

[1] He made his professional debut with the Ogden Raptors of the Pioneer Baseball League,[3] where he appeared in 17 games (with one start) and was 3–2 with a 3.41 ERA.

[16] Stewart suffered from tendinitis in his right shoulder during spring training in 2017, causing him to begin the season on the disabled list.

On December 12, 2019, Stewart was selected by the Chicago Cubs in the minor league phase of the 2019 Rule 5 draft.

[26] On December 11, 2020, Stewart signed a minor league contract with the Los Angeles Dodgers organization.

[28] On July 14, 2022, Stewart announced that he had signed a two-year minor league contract with the Minnesota Twins.

[29] In 11 games split between the Triple-A St. Paul Saints, High-A Fort Myers Miracle, and rookie-level Florida Complex League Twins, Stewart posted a cumulative 0-2 record and 7.71 ERA with 16 strikeouts in 14 innings pitched.

He began the 2023 season with Triple-A St. Paul, appearing in 7 games and registering a 2.08 ERA with a whopping 17 strikeouts in 8+2⁄3 innings of work.

[38] However, on August 9, it was announced that Stewart would miss the remainder of the season after undergoing arthroscopic shoulder surgery.