[2][3][4] Born in Milwaukee, Wisconsin, Crowley's parents struggled with narcotics addiction in his youth and lost their home when he was just ten years old.

Under the mentorship of Reggie and Sharlen Moore, and their community organizing group, Urban Underground, Crowley became interested in issues of policing and local government.

Crowley graduated from Bay View High School and attended the University of Wisconsin–Milwaukee from 2008 to 2012, but left to pursue politics before obtaining a degree.

[7][8] In the February primary election, Crowley came in a close second to state senator Chris Larson, defeating County Board Chairman Theodore Lipscomb, Sr., and businesswoman Purnima Nath.

[12] He resigned his seat in the Assembly effective June 18, 2020, as required to comply with a 2015 Wisconsin law prohibiting a person from simultaneously serving as a member of the legislature and a county executive.