Milwaukee Leaders is a series highlighting the lives and leadership of those in our local community. This issue, we spoke with David Crowley, a two-term Milwaukee County Executive and community organizer.
Milwaukee County Executive David Crowley’s story is one of firsts. In 2020, he became the youngest and the first Black person elected to oversee the state’s most populous county. In 2024, he won reelection with 85% of the vote. That same year, he became the first college graduate in his family, leaving UW-Milwaukee with a bachelor’s degree in Community Engagement and Education.
Crowley’s non-linear path through higher education made obtaining his college degree a particularly satisfying moment. Crossing the graduation stage, the 38-year-old was thinking of his community, his three daughters, and, most of all, his mother, who passed away in 2023.
“I remember, when I won [the election for County Executive], she was ecstatic, she was excited, but she always told me how important it was for me to make sure I went back to get my degree,” Crowley said. “She didn’t get to see me walk across that stage, but just knowing how excited she was was so important for me.”
It had been nearly two decades since Crowley first set foot on UWM’s campus as a sociology major just after graduating from Bay View High School. One semester in, however, financial stressors motivated him to drop out and take up an electrical apprenticeship instead.
“During that time, it was either go to school and continue to struggle, and not know how I was going to put food on the table, or take care of those that were around me,” Crowley said. “I had to make a tough decision. I didn’t know anything about withdrawing from college [and] I ended up failing my entire first semester.”
Soon, though, with the possibility of starting a family also on the horizon, Crowley left trade school to focus on community and political work, a passion realized in his junior year of high school through the leadership organization Urban Underground.
“Growing up was loving and caring but my parents both had their own struggles,” Crowley said. “[Urban Underground] really helped save my life. That [experience] helped propel me in tapping into my power and my potential and understanding community—community organizations, community leaders—and piqued my interest in getting involved in politics.”
Beginning his political career in 2010 working for then-U.S. Senator Russ Feingold, Crowley continued in a number of positions under Wisconsin officials before stepping into the political spotlight.
“I always said I was never going to run for office because I was working for elected officials and, being in this industry, elected officials get all of the blame and none of the credit,” Crowley said. “The moment that I knew this was something I wanted to do was when I felt that it was just time for me to step up…Being evicted three different times, moving so many times every year for about 15 years, having family members who struggled with mental health and addiction, for me, it was really about, ‘How do I stop this cycle?’”
Still today, Crowley says, his early experiences with community inform him as he navigates his responsibilities as County Executive.
“I was born and raised in some of the most vulnerable parts of Milwaukee County, some of the city’s most underserved places,” Crowley said. “When I’m able to go back and remind myself, talk to the people I grew up with and see the progress that they see, when they get excited seeing me talk about my trajectory and where I come from, that helps to keep me grounded.”
Much of Crowley’s focus as County Executive has been on shaping a new image of Milwaukee, which he says has been both incredibly rewarding and challenging.
“I think that we are the political lightning rod, and if you’ve never been here and you rely on everything you’ve seen on the news, you would think that this is one of the worst places in the state of Wisconsin,” Crowley said. “Changing that narrative, changing that perception and building the relationships needed to bring resources back has been one of the greatest challenges ever, because we’re talking about undoing decades, in some cases, of the story we’ve been told.”
Looking forward, Crowley believes addressing Milwaukee’s most pressing issues, like those surrounding racial and socioeconomic equity, is instrumental.
“We’re talking about being one of the most segregated communities in the entire country, being a community where we know that we need access to housing on both the affordability and market rate sides, knowing we’re a community that has to stretch its public transportation and really [making] sure that when the tide rises, all the boats rise,” Crowley said. “People always say that you have to pull yourself up by your bootstraps. I’m just making sure that Milwaukee County has those bootstraps in the first place.”