Hentges attended Mounds View High School in Arden Hills, Minnesota and as a senior in 2014, was the St. Paul Pioneer Press baseball player of the year.

He started 2016 with the Lake County Captains, but had his season ended early after undergoing Tommy John surgery.

Hentges made 30 appearances (12 starts) for Cleveland during his rookie campaign, posting a 1–4 record and 6.68 ERA with 68 strikeouts across 68+2⁄3 innings pitched.

On September 19, 2022, while pitching against the Minnesota Twins, Hentges tossed 2+1⁄3 perfect innings to earn his first career save.

[15] On September 10, it was announced that Hentges would require surgery to repair the labrum and capsule in his left shoulder, necessitating a recovery timetable of 12–14 months.