campaign,” Crowley said. “And I quickly learned that not only did I like the work, but I was pretty good at it. And so in August 2011, County Board Supervisor Nikiya Harris at the time hired me and I worked for her on the county board for 1-2 years before she became a state senator. I worked for her for four years in the state senate and then got bit by that bug to run myself and became a state assemblyman. And so that gave me the opportunity to spend seven years in the State Capitol, understanding the lay of the land, understanding how the sausage gets made and really being able to build relationships. I know exactly how Madison works.”

In 2020, Crowley decided to take his interest in politics to another level and ran for Milwaukee County Executive. Crowley won with 50.05 percent of the vote and became Milwaukee County’s first African American county executive. He has gained a lot of executive experience in the last five years.

“I’ve been leading the largest county in Wisconsin, representing close to a million people, 19 different municipalities, cities and villages of all different sizes. And the issues that we have been able to tackle cut across partisan and geographical lines, real Wisconsin issues. Being able to bring on affordable housing, being able to tackle the opioid epidemic, lowering overdose deaths, being able to make government more accessible while also making sure that we could deliver the largest property tax cut in history.”

Since 2010, Crowley has formed relationships with elected officials from across the state of Wisconsin. And relationships are often the driving force in politics.

“Relationships matter a lot to me,” Crowley said. “And one of my favorite quotes is from Teddy Roosevelt. ‘No one cares what you know until they know how much you care.’ For me, one of the first things that I did when I first got elected to the state assembly is I created note cards with all of my Republican and Democratic colleagues. One side had their face on it and then on the other side, it listed what area they represent and fun facts about them because you need to develop a level of trust, especially when you are talking policies that are going to affect everyone across this entire state. And I think that was really important for not only being able to get things done in the state assembly, but even as county executive because folks have that level of trust. They believe that I am honest and we are able to have open and honest conversations about where we need to go and what we need to do.”

Crowley has been building on those relationships through every level of government that he has served on.

“Individuals whom I have served with in the state assembly when you think I am able to say that I’ve served with Steve Doyle who has been representing the La Crosse area for many years or even being able to work with a Dave Obey up north,” Crowley said. “I have developed relationships with folks on both sides of the aisle who are still serving today and still having friends who served in counties across the entire state, being the county executive and building relationships through the Wisconsin Counties Association and the coalition that we built through the League of Wisconsin Municipalities to make sure that all communities across the state got their fair share back from Madison.”

And he learned early on that integrity is critical.

“If you know Russ Feingold, he was that independent thinker,” Crowley said. “And he worked with folks on both sides of the aisle because he wanted to make sure that people could trust government, working directly with the late Senator John McCain to get money out of politics. He wanted to make sure that folks knew who was paying for things, so that the campaign finance disclosure agreements came from the federal government. He was all about integrity, open and honest. He was all about having real relationships no matter what letter was behind your name. I love the fact that I got that experience before actually dipping my toe into my own political endeavors.”

And most importantly it is the relationship that elected officials form with the voters from all walks of life that is paramount.

“We have to acknowledge that there is a lot of frustration,” Crowley said. “There is a lot of frustration with the Republican Party, depending upon how you feel about the current President in the White House. But also with the Democratic Party, not being able to come with a cohesive message that’s really going to galvanize and unify this space. I think folks want someone who actually cares. Who’s going to come to the table? Who understands their struggle? Someone who has actually built solutions from the ground up on behalf of working families every single day. I don’t come from money. I don’t come from the halls of power. I’ve built my career on building relationships and doing what’s right. And I think no matter where you live across this entire state, folks want someone who is going to come to the table willing to have honest conversations and let those who are directly impacted by the issues lend their voice towards those solutions. As we build these relationships as we go across the state, I think that it’s really about understanding that we aren’t really different. The issues that we are facing, affordability, are affecting all of us no matter where we live. Housing is affecting all of us. We have an aging population. How do we make sure that people can age and live in their homes with dignity. Those are the things that we are focused on within Milwaukee County and those are going to be the issues that we will bring to the state level without focusing on the culture wars and the partisan issues that are used to divide. It’s about how do we bring more people together to tackle the issues that we all care about most.”

If Crowley had to sum up the issues facing Wisconsinites in one word, it would be “affordability,” an issue that impacts working people in the state no matter what their background is.

“The biggest thing, especially as we traveled across this state, is the affordability crisis,” Crowley said. “Whether you are making more money or not, things are getting more expensive. Families are getting squeezed every single day. And we know a lot of this is because of the chaos and economic policies that are coming out of Washington, D.C. But it doesn’t mean that we can’t help Wisconsinites out. For me, it’s about how do we focus on building affordable housing so that no child has to go through eviction and families can have a safe place to lay their heads. And when someone has a safe place to lay their head, it’s much easier to deal with all the other issues and challenges that may be going on within their lives. How do we tackle the fact that people don’t have to go into debt just to send their children to childcare? How do we make sure that we are building family sustaining jobs in every corner of this state and fully funding our public schools to make sure that our children are ready to fill those jobs — not just for the jobs of today, but also the jobs that are coming in the future. So it’s really about coming together and tackling the affordability crisis. But we also knows that it dovetails into housing, public education, good-paying jobs, access to affordable healthcare wherever and whenever people need it, especially understanding the cuts that are going to be coming down the pipeline in the next 1-2 years related to both of our rural and urban communities.”