


So here's the thing: I'm running unopposed for County Supervisor of the 5th District.
You might think that means I can kick back, skip the hard work, and just wait for election day. But if you know me at all, you know that's not how I operate. An uncontested race doesn't mean you've earned anything—it means you have an even bigger responsibility to show up, listen, and prove you deserve the trust you're asking for.
This is personal for me. Not in a political slogan kind of way, but in a "this is literally my life" kind of way.
As a father, I'm at our District 5 parks every weekend with my daughter, and honestly? Those moments are everything to me. I see her joy on the swings, watch families gathering for birthday parties and summer picnics, and feel the incredible community spirit that makes these spaces so special. I also see where we can do even better—making sure every playground is safe and accessible, every park feels welcoming, and every family has green spaces where their kids can run free and imagine big. Every child deserves that, including mine. And yes, I'm absolutely the dad who's mentally drafting park improvement proposals while pushing a swing. Occupational hazard.
As a teacher, I'm in the classroom watching the mental health crisis unfold in real time. Our young people are struggling with anxiety, depression, and a world that often feels overwhelming. They don't need another adult offering thoughts and prayers—they need real support, actual resources, and people who genuinely believe in their potential. I see their faces every day. This isn't abstract policy to me; these are my students.
As a fashion entrepreneur, I've built a business from an idea to reality. I know the 2 AM anxiety of making deadlines, the thrill of a successful launch, and the absolute maze of regulations small business owners navigate. Economic development isn't just a talking point—it's my lived experience. That lived experience runs deeper than my own business. I've watched my mother fight tirelessly for underserved communities and small business owners to get equitable treatment—teaching people how to build their own table when a seat won't be offered. I've fought alongside her in bridging the economic gap through entrepreneurship, understanding that real opportunity means dismantling barriers, not just making speeches about them. Those lessons shaped who I am and what I believe leadership should look like.
As a community advocate, I've been in the trenches fighting for reform and equitable economic development alongside my neighbors. I've learned that real progress means building systems that work for everyone. And I've learned that showing up consistently matters more than showing up loudly.
Here's my promise: Running unopposed doesn't mean I'm taking your vote for granted. It means I have the unique opportunity to spend this campaign doing what I actually want to do as your Supervisor—listening to you, learning from you, and building relationships before I even take the oath of office.
No opponent means no attack ads, no manufactured controversies, no political theater. Just me, you, and honest conversations about what the 5th District needs.
Between now and Election Day, I'll be knocking on doors in every corner of our district. I'll be at community meetings, neighborhood gatherings, and wherever folks are willing to talk. Not because I'm checking boxes or following some campaign playbook—but because I genuinely want to hear from you, learn what matters most to your family, and show you that I care about getting this right.
I'm going to campaign like I'm ten points down because earning your trust matters more than winning by default. The job starts now, not on inauguration day.
This isn't about political ambition or building a resume. It's about the community I'm raising my daughter in, the students I serve every day, and the neighbors I've lived alongside for years. This is home.
So let's do something different. Let's use this campaign to actually solve problems together, to build the future our families deserve, and to show what local government can be when someone is genuinely accountable to the community, not to political machinery.
I'm asking for your vote—not because you have no other choice, but because you believe, like I do, that the 5th District deserves dedicated, authentic leadership that shows up every single day.
Let's get to work.
— LeeVan Roundtree





Thoughts from the trail (and the classroom, and the parks, and wherever else you'll find me)
I want to talk to you, get to know you, so that we can grow the 5th together!
8430 West Capitol Drive, Suite #3030 Milwaukee, WI, USA
campaignmanager@roundtree4the5th.com treasurer@roundtree4the5th.com Leevan@roundtree4the5th.com
Today | By Appointment |
April 7th, 2026
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