No county in Wisconsin has as many voters as Milwaukee. It’s the economic engine of the state and its largest and most diverse county. It also leans heavily Democratic. In 2020, around 70% of the nearly half a million total votes in Milwaukee County went to Joe Biden and only 30% to former President Donald Trump.
That helped Biden win Wisconsin by a margin of just more than 20,000 votes.
Republicans have to do better in Milwaukee and Dane County, says Bill McCoshen, a Wisconsin Republican strategist. “In previous presidential years, we've lost the two of those [counties] combined by more than 360,000 votes. It's almost impossible to make that up in the other 70 counties,” he says. “So, we have to do a better job. And that includes getting suburban voters to come our way.”
Operation Connecting Milwaukee
Milwaukee County GOP chair Hilario Deleon is focused on that mission. The 23-year-old Republican organizer has been engaging with people about the conservative platform throughout Milwaukee County—at street festivals, cultural events and anywhere folks gather. He’s been at events like Juneteenth and UMOS’s Cinco de Mayo celebration.
Deleon has dubbed his approach “Operation Connecting Milwaukee. ” He uses data or in-person outreach to find prospective conservatives and delivers the GOP’s message through neighbors or relatable emissaries. The goal is to find people who may lean conservative but not vote often and also to connect with independents, libertarians, and disaffected liberals.
“For a long time Republicans have kind of left [Milwaukee] alone and thought it's a lost cause,” he says. “Well, now they're starting to wake up and realize that if you lose by less than cities like Milwaukee, you can take the rest of the state because the rest of the state will carry for President Trump.”
Deleon has a deliberate approach. He asks people how they think things are going in the country. If they respond positively, he asks them why and then tries to engage on the issues. If they say “poorly” or “bad,” he deems it an opening for the conservative platform, poking holes in the record of incumbent Democratic President Joe Biden.
“By showing up to places like this, the events like this, it's how we lose by less,” Deleon says. “We show that we're here in the community. Because a lot of times, people say that Republicans aren't in the community. Well, they can't say that anymore because we're here. I'm here. As the chairman, as the leader, I have plenty of other people that could be here. But I choose to be here myself.”
At the Cinco de Mayo event on Milwaukee’s south side, people walk by with little dogs, eating tortas or plucking away at styrofoam containers of elote corn. Deleon tries to blend in at his engagement booth. “How you doin’ folks? How ya doin?” he asks some passersby, who immediately frowns at his Trump signs. “What's wrong? Let's have a conversation. No?”
Deleon acknowledges it might be an uphill battle in some Milwaukee communities. “I have no problem having a conversation — a civil conversation with people. But liberals and leftists, they don't like to talk, they immediately just turn off and tell them nope, nope, nope.”
The allure of conservatism
At Cinco de Mayo, a Trump sign is the central decoration at the outreach booth, leaning precariously against the table, along with a sign for Wisconsin’s Republican U.S. Senate candidate Eric Hovde.
Every so often, the Trump sign is blown over by the wind, and Deleon dutifully picks it back up again. It’s a tenacity Deleon says he has had ever since he was young, when he first got into politics. When he was in first grade, he found a set of Civil War books in a closet in his house. “And I would stay up late at night and I would flip through it and I saw and studied the history of the war, and how we got where we were. I’m a Civil War re-enactor myself.”
Deleon says he was inspired by Republican abolitionists like Abraham Lincoln. “We are one of the only countries that fought a war against ourselves to free our fellow man.”
Deleon says he’s been a loyal Republican since then, even defending his political views throughout high school when Trump was president. “I was treated horribly in the school by students and teachers. So, it really made me want to pay attention more to every single issue that he got done when he was president.”
Deleon was adopted. His biological dad is Mexican, but DeLeon is quick to point out that he’s American – and Hispanic. “If you would break it down by ethnicity, I have Mexican, Spanish, German, Polish. I’m Mr. Worldwide, as one person might put it. But my sister's adopted. I'm adopted. My sister's African American. My mom is a single mom. How are you doing, sir?” he asks someone walking by the engagement booth.
Some Hispanic groups have torn into former President Donald Trump for his descriptions of immigrants. He’s said immigrants who commit crimes are "animals" and “poisoning the blood of this country.” He’s also boasted that he’ll get Mexico to pay for a border wall.
But there is nothing about Trump that gives Deleon pause. Not his record, his platform, his current legal troubles, or his personality. Certainly not his comments about immigrants. “No,” says Deleon. “Let Trump be Trump. Let him be him. He does what he does; you can take the man out of New York, but you can take New York out of the man.”
Treading a fine line on immigration
Just about at this point, a Cinco de Mayo attendee named Tony Garnica walks up to the GOP booth, his Mexican straw cowboy hat shielding him from the sun. “You know, Trump is against immigrants?” Garnica asks. “No, that’s not true,” says Deleon. “He has said many times that ‘I want people to come in legally.’”
“I know, but he says as soon as he gets in power, he's gonna kick everybody out — all the immigrants,” Garnica responds.
“That's not what he means,”Deleon argues.
At various events this year, Trump pledged “the largest deportation in the history of our country.” But Deleon says that didn’t happen in Trump’s previous term and claims Trump only wants to deport criminals.
Trump has said he wants to use the National Guard to remove migrants and would start by using local police forces and focusing on any migrants with a criminal record.
Garnica and Deleon continue to debate about Trump’s character and policies.
“You know who is gonna [get] kicked out? All the Mexicans,” Garnica says.
Deleon interjects that he’s part Hispanic himself and Garnica explains he’s talking about undocumented Mexicans.
“Are you illegal?” Deleon asks Garnica. “No.” Garnica responds. “Then what are you worried about?”
“I'm worried about my people, what do you mean what I worry about?” says Garnica.
“What about the American people?” he asks. “What about the American people that can't get jobs? What about the American people that are homeless? What about the American people that are having issues with drugs? What about those people?”
An eye on the prize
Garnica is exactly the demographic Deleon is looking for. He’s Hispanic and says he leans conservative. But this year, Garnica says he’ll be voting for Biden.
Deleon doesn’t have to win everybody over — just enough people to push up Trump’s ceiling in Milwaukee. In this state, every vote counts. Four of the last six presidential races had margins of less than 1 percentage point.
At the Cinco de Mayo event, two paletas sellers —hawking the creamy and fruity Mexican popsicles— ring dueling bells as they compete for customers. Deleon is competing in a way, too, for voters. And he’s alright with that.
