Who Is… David Crowley? Milwaukee County’s Trailblazing Nice Guy

From 53206 to the Courthouse: Milwaukee County’s Ground-Level Executive

Milwaukee County is a place of sharp contrasts—home to both bustling lakefront neighborhoods and long-neglected blocks, local pride and generational struggle. At the center of it all is David Crowley, the first Black and youngest person ever elected as Milwaukee County Executive. Since taking office in 2020, Crowley has tried to steer the state’s largest county with a steady hand and a focus on practical gains: public health, fiscal repair, housing, and access to services.

He’s not flashy, but he’s rarely idle. His work takes him from the Capitol to neighborhood clinics, and his personal story shapes how he governs.

The journey

Crowley grew up in Milwaukee’s 53206 ZIP code—an area known nationally for high incarceration and poverty rates. His childhood was shaped by instability: both parents struggled with addiction, and his family at times lost housing. But Crowley credits local mentors, including those at Urban Underground, with helping him find direction as a teenager.

After graduating from Bay View High School, he attended the University of Wisconsin–Milwaukee. Though his early political work interrupted his studies, he returned years later to finish what he started—earning his bachelor’s degree in community engagement and education in 2024, becoming the first in his family to graduate college.

Politics Outside the Limelight

Crowley got his start in government working behind the scenes. He served as a legislative aide, then a policy director in the state Senate, learning the mechanics of policymaking before running for office himself. In 2016, he was elected to the Wisconsin State Assembly, representing the 17th District on Milwaukee’s north side.

There, he focused on mental health services, criminal justice, and transportation. His ability to work with both Democrats and Republicans helped him earn respect across the aisle—skills that would serve him later when managing a county with shrinking budgets and growing needs.

A County in Motion

Crowley won his first election for County Executive in April 2020, in the early days of the COVID-19 pandemic. He was sworn in on his front lawn, masked and socially distanced, with a folding chair and a Bible. It was a quiet start to a high-pressure job.

Since then, Crowley has tackled a long list of county challenges: an aging mental health system, a broken funding model, and public demands for more equitable services. He launched the “No Wrong Door” initiative to make mental health support easier to access and expanded opioid harm-reduction efforts, including free naloxone stations and syringe services.

His administration also pushed for a dedicated affordable housing fund and expanded workforce development partnerships, especially in neighborhoods hit hard by disinvestment.

In 2023, he helped broker a deal in Madison that resulted in a historic overhaul of state revenue sharing laws. That legislation—Act 12—gave Milwaukee County new authority to raise local funds and keep essential services afloat, including transit and public safety. It was a rare bipartisan win, and Crowley was at the center of it.

Family and Focus

Crowley lives in Milwaukee with his wife, Ericka, and their three daughters. He’s open about how becoming a parent changed his priorities. “The policies we pass don’t just show up in headlines,” he said in a recent interview. “They show up in our homes, our schools, and our streets.”

He’s a familiar face in community meetings and civic groups. He’s been involved with the Milwaukee NAACP, the Urban League Young Professionals, and the ACLU of Wisconsin. His supporters say his style is measured and intentional—more about listening than leading with a megaphone.

The Second Term

Reelected in 2024 with over 80% of the vote, Crowley is now focused on long-term problems that never left the table: closing racial health gaps, modernizing county infrastructure, and making sure public services work for more than just downtown ZIP codes.

He’s also overseeing major transitions. The county is phasing out its legacy mental health complex and shifting services to community-based providers. Public transit is moving toward electric buses. And more resources are being directed to housing assistance and eviction prevention—often funded by dollars Crowley helped free up in his deal with the state.

A County Executive With a Backstory and a Backbone

Crowley doesn’t fit the mold of the traditional Wisconsin politician. His background isn’t traditional. His style isn’t theatrical. But supporters say that’s what makes him effective.

He’s not trying to win the room. He’s trying to keep the machinery of county government moving—quietly, steadily, and with the awareness that for many residents, that machinery is their last safety net.

In a county where the problems are big and the stakes are personal, David Crowley’s work is grounded in everyday questions: Who gets a bus route? Who has a clinic nearby? Who can afford to stay in their home?

Those aren’t just policy issues. For Crowley, they’re personal.

Milwaukee County, Wisconsin, stretches across urban streets and suburban enclaves, a region where grit meets diversity and politics pulse with purpose. Since 2020, David Crowley has guided it as county executive—a homegrown leader whose journey from a tough upbringing to the top office reflects both personal drive and what he calls a commitment to equity. A former legislator, a father, and a voice for the underserved, he’s spent his tenure bolstering housing, curbing reckless driving, and pushing racial justice, all while balancing a degree nearly two decades in the making. In a fractured political era, Crowley’s steady climb offers a lens into leadership forged by community and resolve..

Now in his second term, he faces a courthouse funding shortfall, overdose spikes, and economic shifts. His answer? The same playbook—data, partnerships, and a long haul mindset. In a political world of bombast, Crowley’s quiet grind stands out, a testament to a kid from 53206 who turned struggle into strength.