Why Crowley Won in Wisconsin: Reflections from an Exhausted Intern

By Zachary Suri

It was my fourth day as a politics reporting intern at the Milwaukee Journal Sentinel, and I was standing at a sweltering bus stop in Downtown Milwaukee on an early morning in June.

Plagued by years of financial crisis, the Milwaukee County Transit System was announcing a modest surplus for fiscal year 2026. Milwaukee County Executive David Crowley, then slowly fading out of the Democratic primary for Governor, stood to speak.

Instead of simply celebrating the surplus and touting his administration’s efforts to turn around a transit system that had, only a year before, blindsided county leaders with a surprise $10.9 million deficit, Crowley did something very rare in politics. He talked about the problems to come. He warned reporters like me, half-asleep on a Thursday morning, that the bus system was facing a looming fiscal cliff in 2027. More work had to be done, he said. Milwaukee County needed more help from the state.

Two months later, after perhaps the most remarkable stretch in the history of any recent campaign, Crowley might soon be in a position to make that happen. After his surprise victory in the Democratic primary for governor on Tuesday, Crowley is favored to defeat the Republican nominee in November.

On July 9, I watched in a nearly empty ballroom at the top of the Milwaukee Athletic Club as Crowley officially dropped out of the race, endorsing Lieutenant Governor Sara Rodriguez. A week later, she dropped out. And a day after that, a block from that sweltering bus stop, Crowley announced he was reentering the race with the coveted endorsement of Wisconsin’s popular two-term governor Tony Evers.

When Rodriguez announced on July 12 that she was firing her campaign manager after discovering major discrepancies in her campaign finance reporting—the scandal that eventually led to her bowing out of the race—I was driving to Milwaukee County’s Housing Authority to report on Crowley’s affordable housing programs.

That reporting, more than any of my time covering the race, revealed the most about Crowley as a politician.

Milwaukee County has had one of the lowest homelessness rates of any major city in the country almost every year of his tenure. In 2025, there were only 54 unsheltered homeless in a county of over 900,000 people, and none under 24 years old, according to federal data.

Driving around the county with his housing director James Mathy, I learned why.

Milwaukee County has done something very simple, and apparently effective. It has combined a half dozen federal housing programs and behavioral health services under one roof. County officials go into the streets to encourage homeless people to move into transitional or permanent housing, paid for by county housing vouchers. The county has provided small chunks of money, much of it from federal COVID relief funds, to developers across the county to encourage affordable housing development.

Much has been made of Crowley as a “moderate” or “establishment” candidate, the one endorsed by the sitting governor to oppose the democratic socialist frontrunner. But as county executive, probably the second-most powerful position in the state, Crowley has championed progressive policies like housing-first homelessness outreach.

The difference is none of it has been flashy. Few in Milwaukee know that their community has one of the lowest homelessness rates in the country. Until a few weeks ago, Crowley himself hardly seemed to mention it. Just as he did at that bus stop, he often prefers to focus on the problems that still need to be solved.

Milwaukee County government is not known for its efficiency, its pragmatism, or its fiscal stability. Just the opposite. But Crowley is the first to admit that those problems persist. He has embraced a progressive politics that is focused on slowly solving them. Gap financing and social service consolidation are hardly sexy political programs. They are pragmatic approaches to difficult policy questions that Wisconsin’s largest county appears somehow to have gotten right.

The first time I spoke with Crowley was at a press conference announcing a new county initiative to impound vehicles involved in reckless driving. Standing with sheriff’s deputies, Crowley spoke forcefully to the problem of dangerous driving in Milwaukee. It is a serious public safety issue in Milwaukee County (trust me when I say this — in less than two months, two different cars I was borrowing were totaled on Milwaukee streets). This policy, Crowley argued, was a pragmatic solution, one that empowered law enforcement.

Crowley’s opponent in the race embodied the opposite approach to public safety. In the wake of a police shooting in her assembly district in Madison last month, Francesca Hong called the shooting an “execution” and criticized city leaders for clearing an encampment that shut down a busy intersection for days. For weeks, protestors disrupted life in the state’s most liberal county, forcing small businesses to close and forcibly ending a popular outdoor concert series on the state capitol grounds. Meanwhile, Hong was on CNN defending old tweets calling for the cancellation of Thanksgiving.

In the end, voters in Madison went for their ‘favorite daughter’ with surprisingly low margins on Tuesday. Hong did not even win a majority in Dane County, and she lost many of the more populous wards on the city’s wealthier and whiter west side.

Crowley managed to bring together a coalition of voters that included the wealthiest zip codes in the state and the poorest. He won liberal college professors on the west side of Madison, wealthy suburbanites in Whitefish Bay, and huge margins from Black voters on the north side of Milwaukee where he grew up.

In the days leading up to the election, Crowley barnstormed across the state with Governor Evers, but he was still polling far behind Hong. Republicans spent millions trying to boost her campaign, assuming she would be easier to beat in November. Hong was nearing 50% of the vote in most polls, with more than 30% of voters undecided. But somehow, Crowley won almost all of those undecided votes. And establishment Democrats everywhere breathed a collective sigh of relief. “For now, we polka,” Evers tweeted. “Tomorrow, we’re back at work to win.”

As Republican nominee Rep. Tom Tiffany told his supporters Wednesday morning, chances are Thanksgiving is safe this year. His chances of making it to the governor’s mansion? Not as good.

Zachary Suri is a senior at Yale University studying literature and history. He is an aspiring political journalist with experience covering policy and politics in Connecticut, Texas, and Wisconsin. You can read more of his recent reporting for the Milwaukee Journal Sentinel here.