After dropping out at 19, Milwaukee County Executive David Crowley will graduate from college this weekend 

Like many parents of younger children, David Crowley is usually up at the crack of dawn.

After he helps his three daughters —  ages 5, 7, and 17 — get to school, he often heads to his office in downtown Milwaukee.

Next is where his day gets a little hectic.

That’s because Crowley, 38, is the Milwaukee County Executive. But for the past three years, he’s also been attending classes at the University of Wisconsin – Milwaukee in an attempt to get his college degree.

Crowley has juggled his daily responsibilities with the county — like meetings and hearings — with daily responsibilities at school — lectures and presentations.

It’s been a difficult journey at times. He’s often up until midnight or later working on homework. But he said it’ll all be worth it when he walks across the stage at UW-Milwaukee Panther Arena Sunday to receive his diploma nearly 20 years after he dropped out of college. 

“I’m excited, I’m anxious, but I also have a heavy case of senioritis,” Crowley said in an interview with WPR.

Crowley, a former representative in the Wisconsin State Assembly, said he’s getting his college degree for his three daughters.

“I wanted to be an example for them,” he said.

He also wants to show others across Milwaukee and Wisconsin that higher education is important.

“I wanted to not only show the next generation, our young leaders, that this is possible and how important an education is, but also other non-traditional students who are like me … that they can go back,” Crowley said.

Crowley is the first Black person and the youngest person to be elected Milwaukee County Executive. He took office in 2020 and won his reelection bid earlier this year.

Sunday, he’ll achieve his next feat after he receives his degree in community engagement and education from the UWM School of Education.

The Milwaukee native will also deliver the commencement speech for his graduation class. When he gives that speech, he’ll be thinking of his late mother Valerie, who died last year.

“She was excited when I became the county executive, but she never stopped talking to me about enrolling in school,” Crowley said. “And I will tell you the day that I enrolled in school, she was just as excited as I was being county executive.”

“If she was at the graduation, she’d be screaming at the mountain tops,” he added. “I probably wouldn’t be able to get through my speech, because I’d probably hear her the entire time.”

‘The art of time management’

Crowley first attended UW-Milwaukee in 2006. He dropped out during his first semester after he said he got into an electrical apprenticeship. He tried going back to school over the years, but he decided to go all in and pursue a college degree around three years ago.

Some days, he swaps out his office at the Milwaukee County Courthouse for a study room on campus.

“I definitely learned how to master the art of time management,” Crowley said.

“Some folks have football Sunday, I had homework Sunday,” he added. “I just missed out on a lot of things, because I knew that the sacrifice would pay off long-term.”

Crowley had a class at 10 a.m. this semester.

“So I may have a meeting for work before class, come to UW (Milwaukee), attend class and then I have my duties even moving forward,” he said.

While attending school, Crowley would sometimes get home after 8 p.m. He’d use that time to spend time with his family, sometimes even doing homework at the kitchen table with his kids.

“But if they were done with their homework or didn’t have any homework, what I would do is use that time to spend with them, because they knew that Daddy was always busy,” Crowley said.

He was sometimes forced to skip class or meetings due to his commitments. A few months ago, he had to miss class due to meetings he had to attend with the Large Urban County Caucus.

“I had to, you know, let my teachers know that this is something that I have to do and, and I’ll be honest with you, not all my teachers knew that I was a county executive,” Crowley said.

Other students he had classes with sometimes didn’t know of his position until he told them about it. But he said conversations with other students allowed him to, “have real conversations and learn about the experiences and the interests of those who were somewhat younger than me.”

“It was pretty cool to be able to break that ice and them to learn from me, and vice versa,” Crowley said.

Crowley is first in his family to graduate from college 

Like his friend Milwaukee Mayor Cavalier Johnson, Crowley grew up in the city’s troubled 53206 zip code. Only around 7 percent of residents above the age of 25 in that zip code have a bachelor’s degree or higher, according to U.S. Census data.

“So I want to be that inspiration, that example, for many people in 53206, but quite frankly, who live in southeastern Wisconsin and in this state, who are second guessing whether or not they should take on a higher education,” Crowley said.

Crowley is the first person in his family to graduate from college.

As county executive, Crowley has fought for more state funding for local municipalities, seeing that come to fruition with the passage of Wisconsin Act 12. He’s pushed for more money to go towards affordable housing and to fight the opioid epidemic, which has taken a toll on Milwaukee County in recent years.

But he also has challenges ahead, including navigating a difficult county budget in the coming years. 

When asked about his next steps, he didn’t rule out running for higher office.

“Opportunity comes at the corner of preparation and luck and so do I have ambition to run for higher office? Absolutely,” Crowley said.

However, he also didn’t rule out going in another direction, another reason he said it was important for him to have a college degree.

“Don’t get me wrong, I love my job, but if I decided to go into the private sector or start my own business or be an entrepreneur … I don’t want not having a degree to hold me back,” Crowley said.