India, Nov. 3 -- David Crowley's political pitch starts at the kitchen table, not the state Capitol. He grew up in a household where evictions, hunger and a potential electricity shutoff were concerns, and he says Wisconsin government needs to focus on the costs families can barely afford.

Crowley, 40, is Milwaukee County's executive and previously served in the Wisconsin Assembly. His father was an electrician and his mother worked in the service industry, but both struggled with addiction and mental-health issues.

Crowley has described not knowing whether he would come home from school to find the family home intact or their belongings on the street. That experience informs a more recent personal milestone: Crowley dropped out of coll...