MADISON, Wis. — David Crowley, the Democratic nominee for Wisconsin governor, ranks as the most surprising winner in this year’s turbulent primary season. But the Milwaukee County executive’s against-the-odds story began long before election night.
Crowley’s parents became addicted to crack cocaine, and his family was evicted three times before he graduated high school. At times, he and his two brothers lived with no electricity or heat.
He spent his first 10 years in northern Milwaukee’s 53206 Zip code, long infamous for having one of the nation’s highest incarceration rates. By the time Black men there reach the age of 35, “half of us growing up in that Zip code would have spent some time behind bars,” said Milwaukee Mayor Cavalier Johnson, who was a year behind Crowley in high school.
His personal history has not gotten much attention outside of Milwaukee, having been overshadowed by the wild, 34-day stretch before Wisconsin’s Aug. 11 primary.
In less than five weeks, Crowley left the race, saying he saw no path to victory; endorsed the presumed front-runner, only to see her drop out amid controversy a week later; then jumped back into the contest with the backing of Gov. Tony Evers (D). Finally, and most astonishingly, Crowley closed a double-digit gap in pre-election polls to defeat a high-profile democratic socialist by half a percentage point.
Now, the 40-year-old chief executive of Wisconsin’s most populous county could make history in November by becoming the state’s first Black governor.
None of that would have seemed like what destiny had in mind for Crowley. His first home was one his father, a master electrician, bought from the city in 1984 and restored. His vivacious mother worked various jobs, including as a waitress and bartender.
But as both became hooked on crack, the family’s situation spiraled.
His mother abandoned the boys and their father for a couple of years. She returned, still in the grip of drugs and mental illness, and Crowley’s father moved out to try to put his own life back together. After eighth grade, Crowley got a job with a lawn maintenance company, he said, because it was “the only way that I was going to buy my own clothes, buy my own shoes.”
The third time the family was evicted, Crowley, a high school sophomore, came home to find their meager possessions on the sidewalk. Their former house on North 23rd Street was eventually demolished and is now a vacant lot.
His father overcame his addiction during Crowley’s early high school years, while “my mother took a little more time,” he said. “But you know, watching them go through what they went through, their challenges, helped me understand resilience.”
As a politician, Crowley tends to frame issues in technocratic policy terms. He speaks of how “housing instability” is a “critical social determinant.” But he roots his priorities in the scorching experiences of his life. “How can you focus on your own education?” he said. “How can you focus on your own health care or job opportunities when you don’t know where you’re going to lay your head down at night?”
Unknown to many voters
At a time when the Democratic Party is beset by fierce ideological struggles, Crowley prides himself on pulling factions together.
A second-term assemblyman when he ran for county executive in a nonpartisan election six years ago, Crowley eked out a narrow victory over a better-known, more liberal rival to become the youngest-ever and first Black executive in a county that is more than 60 percent White. One of his predecessors in the job was Scott Walker, Wisconsin’s famously hardline-conservative former governor.
In 2024, Crowley cruised to reelection with 85 percent of the vote. He carried the poorest wards and the richest, the majority-Black and majority-White, the most Democratic and most Republican.
That same improbable coalition fueled his primary win in the Democratic primary for governor, but he has yet to be tested against a Republican opponent.
As county executive, Crowley put together tens of millions in private and government funding to build affordable housing developments in Milwaukee’s suburbs, something that had never happened before.
He also secured a near-doubling of the county sales tax, from 0.5 percent to 0.9 percent. The increase was part of a budget deal with the tightfisted, Republican-controlled legislature, averting drastic service cuts that would have included eliminating half of the Milwaukee County Transit System’s bus routes. That bargain is now being tested on the campaign trail, where Republicans are hammering him for raising taxes.
But even after Crowley achieved his stunning primary upset over democratic socialist Francesca Hong in the Aug. 11 primary, he remains unknown to many in the Badger State. A late-August Marquette poll found close to 40 percent of likely voters said they didn’t know enough about him to have an opinion, more than double the percentage who said that about his Republican rival, three-term congressman Tom Tiffany.
Tiffany, who faced no significant primary opposition, has been endorsed by President Donald Trump and supported Trump’s false claim that the 2020 election was stolen. He signed onto a lawsuit that would have thrown out Wisconsin’s electoral votes in favor of having the legislature pick the winner.
Having assumed along with the rest of the political world that he would be running against Hong, Tiffany is rushing to paint Crowley with the radical-left tag Republicans had planned to use against her. The GOP nominee’s first general election attack ad against Crowley claimed there is “no real difference between him and socialists.” He has also referred his opponent as “Milwaukee County tax collector David Crowley.”
Tiffany is also trying to flank Crowley on the flash point issue of data centers, branding him “Data Center David Crowley.” One Tiffany ad features a selectively cut video clip in which Crowley says Wisconsin has an opportunity to become “an AI and a data hub not only for the entire country, but for the entire globe.”
Tiffany’s campaign did not respond to a request for an interview.
While opposing a moratorium on data centers, Crowley has said local communities should have the final say on where they are located, that they must follow environmental safeguards and contribute to bringing down utility rates.
He faces a separate challenge in unifying his own party after the divisive primary. Hong began campaigning on Crowley’s behalf within days of losing to him.
In the 2024 presidential election, Wisconsin was the most closely divided state in the country, with Trump winning by a mere 0.86 percent, or less than 30,000 votes. But it is less a purple state than one that is both red and blue, electing one of most conservative members of the U.S. Senate, Republican Ron Johnson, and one of the most liberal, Democrat Tammy Baldwin.
Wisconsin elections tend to be “a tie, and the ball bounces one way or the other at the end,” said former state Democratic chairman Mike Tate.
Evers, the Democratic governor, whose 11th-hour backing of Crowley fueled his primary win, continues to advise him. “At the end of the day, in Wisconsin, you have to spend your time in all 72 counties and talk to people directly, making sure that you’re listening at the same time,” Evers, who did not seek a third term, said in an interview. “That’s how you win. I know that, and he knows that.”
‘Your name is David’
Though fate didn’t throw many breaks to young David Crowley, something transformative came his way in 2002.
It happened in the raucous lunchroom of Bay View High School. Reggie Moore, who with his future wife Sharlen founded a new youth-development group called Urban Underground, was at a table with informational brochures and applications when he laid eyes on a lively 10th-grader holding court with his friends.
Moore summoned Crowley, he recalled, “and he’s kind of like, ‘Okay, what is this?’”
Urban Underground’s after-school program gave him direction and mentorship, and helped him understand the world around him, Crowley later recalled. “It taught me how to love myself, how to love my community, and it just changed my life,” he said in an August interview on the podcast “Milwaukee Uncut.”
Crowley became especially interested in criminal justice, having grown up seeing how Black men were treated under the existing system. Moore urged him to learn the history of the civil rights movement and impressed upon him that “policies make a difference and leadership makes a difference.”
Building self-worth was central to the program. Crowley was known in high school as “Dirty,” a reference to his skin tone. “No,” Sharlen Moore, now a Milwaukee alderwoman, admonished when she heard him answer to that nickname. “Your name is David.”
The Moores saw other worrisome signals. Crowley sometimes showed up late to meetings — or missed them entirely — because he had no transportation. They stepped in where they could; some nights, he slept on Sharlen’s couch.
“It was very clear that David had power, he had leadership, he had agency. However, the conditions in our lives — trauma, exposure to violence — all of those things can impact and suppress the best things about us,” said Reggie Moore, who went on to lead Milwaukee’s Office of Violence Prevention.
Though still in high school, Crowley left home two weeks after his 18th birthday. After graduating in 2004, he joined Public Allies, an AmeriCorps program aimed at developing young leaders in poor and minority communities. (Former first lady Michelle Obama founded the Chicago Public Allies chapter in 1993, and called it “the best job I ever had.”) Crowley helped former inmates find jobs and housing, worked in an alcohol and drug program and did community engagement for a YMCA.
In 2006, he enrolled at the University of Wisconsin at Milwaukee, but dropped out after his first semester to pursue an electrical apprenticeship because his girlfriend was pregnant. He assumed he was starting a family — until six months later, when a paternity test showed he was not the father.
Crowley was devastated, and once again, looking for his life’s direction.
In 2010, he went to work for Sen. Russell Feingold’s reelection campaign. It was a disastrous year for Democrats and Feingold was among the casualties. But for Crowley, the experience widened his lens. He loved political organizing and discovered he was good at it.
‘Mom, we forgive you’
Crowley took a job as a legislative aide to Milwaukee County Supervisor Nikiya Harris Dodd. When she was elected to the state Senate in 2012, he followed her to Madison as her policy director.
By then, both his parents had gotten sober, and each would remarry. When his mother developed blood clots after a hysterectomy, Crowley stayed with her as she recovered and commuted 80 miles each way to work. For the first time, the two of them discussed the brokenness of their shared past.
As he began to understand the depth of his mother’s guilt over what she had put her sons through, Crowley’s anger at what had happened in those years finally began to lift. He realized they all had some healing to do. “Hearing the pain in my mother, hearing the sorrow, hearing the depression from our growing up — when I heard that, it moved me,” he said. “I told her: ‘Mom, we forgive you.’”
He added: “At that moment, it wasn’t about us forgiving her; it was about her forgiving herself.” Crowley also decided it was time to repair his relationship with his father. His mother, Valerie Crowley, died in 2023; he remains close to his father, who is also named David.
Crowley ran for office in the spring of 2016, seeking a spot on Milwaukee’s City Council. He came in third. A month later, he ran again, for a seat in the legislature, and won.
Three days after losing his first race, Crowley married Ericka Bowen. They had met two years before, when she interviewed him at a Starbucks for a magazine article she was writing.
As he took a risky leap toward elected office, Bowen paid the bills so that he could take a leave from his job. Together, they have raised her daughter from a previous relationship, and have two of their own.
In December 2024, Crowley gave the fall commencement address at the University of Wisconsin at Milwaukee. It would not have been remarkable except for a bit of unfinished business: Nearly two decades after dropping out of that institution, he crossed the stage to receive a bachelor’s of science in community engagement and education.
While working full time as county executive, Crowley spent the past three years attending classes and doing hours of homework nearly every night.
“I’ve learned a lot on this path — sometimes the hard way, sometimes the easy way — but always with the intention of setting a better example for my three daughters,” he told his fellow graduates. “When I decided to return to school, I wanted my kids to know that it’s okay to start over, to reinvent yourself, and to challenge yourself — even when life feels overwhelming.”
Crowley added: “We all have the ability to create the life we want.” But for some, building that life means writing their own comeback story — again and again and again.
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