Wisconsin election: Milwaukee County GOP, Democratic chairs debate

We'll remind you that this is not a typical newscast. This is a little more casual. This is more podcast-like. So we're just going to bring our guests in right now. And we have two special guests here to join us from opposite sides of the aisle. We have Hilario De León and we have Kiwan Jennings. Tell us a little bit about yourselves, who you are, and your backgrounds. Yeah, so I'm chairman of the Republican Party of Milwaukee County. I was elected at the age of 22 back in 2023 and then reelected back in 2025. I'm 25, a very grassroots person and I've really worked on rebuilding the county party to be more of an entity within the county politics here in Milwaukee County. And it has truly been an experience and a ride. And you, Kiwan? Something similar. We started around the same time, but I know... You're chairman of the Democratic Party of Milwaukee County, correct? I am. I've been chair about two months now. I'm not quite the same, but... Welcome to the field. Thank you. I've been organizing for years. I just enjoy the work. I'm passionate about it. I typically talk to folks who are not really interested and try to change mindsets, so I love it. Let's start by talking about the governor's race, because I think a lot of people are interested in that. Obviously, top of the ballot. How are you feeling about this? I hate saying how are you feeling, but it's an exciting night. You've been working for months and months leading up to today. So I'm just curious how you're feeling. Optimistic. Do you believe the polls? Do you not? Well, I think going into Election Day. Okay. Republicans are typically underpolled because Republicans don't tend to answer polls. So we're often seeing, what I'm hearing out in the field from fellow county chairs across the state, is that they're seeing higher turnout in a lot of key areas that are needed. Waukesha has very high turnout right now. As a matter of fact, if Waukesha, if we get to at least 60% Republican turnout, Tom Tiffany is going to be the next governor. For us in Milwaukee, it's the lose by less mentality. We're not going to win the county outright. All we have to do is increase the voter percentage by a few points. What we've done differently this cycle is that we put together a precinct, a ward captain, precinct captain system under our initiative called Operation Connecting Milwaukee, and we had 116 ward captains throughout the county out there actively knocking on doors and talking to people that are low prop Republicans that need to turn out and vote this cycle. I noticed as you were talking, Kiwan, you were taking notes. I'm curious what you were noting. Yeah, you mentioned Milwaukee is we only really need. Roughly 50% of the county to come out and support us and I feel strongly about that, particularly on the north side. I just recently heard on the north side there in one polling place in particular, there were 200 new registrations at a polling place that's not very active. And so to put it plainly, and I do believe the black vote may. Flip this thing if they're motivated. How is this race impacted by, like any midterm, you don't have presidential candidates on the ballot. We know that Donald Trump has been able to get voters out in Wisconsin. He's not on the ballot, at least not in name. He certainly has an influence, and he casts a large shadow over this entire election. But how is it different when Donald Trump is not on the ballot? It's very different because it's a matter of whose base is going to turn out. And the president has a very strong approval rating within the party itself, you know, differently from what national polls are saying at, you know, across the country and how people are feeling. But when those voters, those Trump voters show up. Republicans win elections, and so it's just a matter of, again, who is going to turn out, what base is going to turn out, and Republicans have a turnout problem in this state in midterm elections that is just historically known, and we've been noticing that, and that's what we've been so focused on is saying, like, look, and the president has been on the campaign trail the last couple weeks of the campaign and really encouraging voters from across the country, turn out and vote, pretend, like, act as if I'm on the ballot. He hasn't come to Wisconsin, though. He still has, As you said, it still has a big impact. And people can still see the rallies and everything on social media. Just because the president doesn't come to Wisconsin doesn't mean that people from Wisconsin aren't paying attention to what the president is saying and doing. I have more questions about that, but I also want to hear your thoughts. Where do I start? All right, let's get started. In a sense, Donald Trump is on the ballot. Let's talk about it. Tiffany voted 100% of the time with Trump. And so that means... What we're dealing with right now is a direct correlation to those votes, whether it's higher gas prices, groceries, you name it, life is tougher now. And I would say, Tom Tiffany, Trump may not be on the ballot, but the voting record of Trump is on the ballot.