Before stepping into the national spotlight as the Democratic nominee in the Wisconsin governor’s race, David Crowley was shaped by Milwaukee. 

Crowley was born and raised on Milwaukee’s North Side. His father, an electrician, and mother, who worked in the service industry, both struggled with addiction and mental health challenges. He has previously talked about his family’s experiences with evictions and poverty and how it connects to his past and current work.

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He spent time working with local groups and nonprofits like Urban Underground, Public Allies Wisconsin and Project RETURN before working behind the scenes in politics, serving as representative for District 17 in the Wisconsin State Assembly and being elected Milwaukee County executive in 2020.

Some of Crowley’s mentors, former colleagues and friends/mentees are reflecting on his run for governor and what it could mean for Milwaukee. 

“Win or lose, he’s still in the fight to make positive change,” said Lavon Phillips, who Crowley mentored when he worked at Urban Underground. 

Learning at Urban Underground 

Crowley started participating in Urban Underground, an organization founded by Sharlen and Reggie Moore to help youths develop leadership and organizing skills, as a junior at Bay View High School.

Sharlen Moore, who is now the District 10 alderperson and has publicly supported Crowley’s candidacy for governor, said he was inquisitive, outgoing and social as a teen and used the challenges in his life to drive him toward solutions.

“It was sort of twofold, where he learned a massive amount of skillsets of how to connect with people and how to use his voice for change,” Moore said of his time at Urban Underground. “He also knew that he had a family, people that loved and cared for him.” 

Glenda Byfield was the only high school freshman when she joined Urban Underground. She said Crowley helped her feel welcome and included.  

“He would sit next to me when we’d go on long rides and just talk and make me feel like I had somebody there who actually paid attention and cared,” she said. 

Byfield, who now lives in Virginia and works for the federal government, said her personal view of Crowley is that he is a genuinely good human and takes responsibility for his actions. 

If he becomes governor, she and Moore said they think Crowley would put people first throughout the state, while not forgetting about Milwaukee. 

“I know that historically, the city is underfunded, and the citizens struggle to meet their basic needs,” Byfield said. “And I think with David at the helm, that’ll be eased quite a bit.” 

Working with Public Allies and Project RETURN 

Crowley is an alumnus of Public Allies, a 10-month apprenticeship program through AmeriCorps. Allies in the program are placed at nonprofit organizations and come back together as a cohort once a week for collaborative training. During his time in the program, he worked at Project RETURN. 

Wendel Hruska, executive director of Project RETURN, said Crowley worked as a case manager and helped individuals returning from incarceration with reentry needs like housing and employment. 

“Doing it at a very young age, 18 years old, really shows the heart that he has for the community,” Hruska said. 

Public Allies was focused on teaching its leaders to be rooted in community assets, to engage diverse people, build trust and collaboration, have integrity and be a continuous learner, according to Paul Schmitz, then the CEO of Public Allies and the founder of Public Allies Wisconsin.

“I’m so proud of David because he manifests and exemplifies those values as well as anybody I’ve seen,” said Schmitz, who is now a nonprofit and leadership consultant and senior adviser at Collective Impact Forum. He said he got to know Crowley better when reaching out to him to participate in alumni initiatives. 

He thinks that Crowley winning the race would help Milwaukee. 

“Beyond how much I’m inspired by David and believe in David, I think Milwaukee needs friends in Madison who recognize Milwaukee is the engine for the state and want to invest in Milwaukee and not harm Milwaukee,” Schmitz said. 

Urban Underground as a mentor

Milwaukee County Executive David Crowley, left, addresses the moderators during a gubernatorial debate at Marquette University on Oct. 21. Former colleagues of Crowley shared their thoughts about him with NNS. (Andy Manis for Wisconsin Watch)

Crowley eventually worked as a staffer at Urban Underground, according to Moore. 

Phillips, who joined Urban Underground as a sophomore in high school, remembers Crowley encouraging the youths to commit to building safe and sustainable communities and telling them that their voices mattered. 

“If you did not talk, he would ask you a question,” he said. 

The two have stayed in touch as friends over the years. 

Phillips lives and works in Atlanta now. He said he thinks Crowley winning the governorship would be amazing for Wisconsin, especially for young Black men and women. 

He remembers taking a trip to Atlanta as part of Urban Underground and meeting Black male city leaders and university presidents. 

“I feel like that did something for me to be able to see that, because when I was young, I didn’t see a lot of that,” Phillips said.

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