'Your Activities in Milwaukee Could Potentially Save the Whole of Civilization'

MILWAUKEE — The young man stood on the back bumper of a Ford Expedition pulling a trailer covered in hay bales and Trump signs. His shirt said Trump. His hat said Trump. “Let’s go win in November!” he hollered into a handheld microphone hooked up to a makeshift sound system bungeed to the top of the SUV. “Who’s ready to save our country?!”

The Fourth of July parade in the community of Cudahy on the south side of Milwaukee County rolled up Packard Avenue, past a big, old metal forging factory, by a dive bar on what seemed like every block, through a pocket of deep-blue Milwaukee County that four years ago was blue by only a bit but this year could be blue not at all. “God bless Trump!” somebody said from one side of the street. “Fuck you!” somebody said from the other. “Trump 2024!” a white woman shouted. “Get the fuck out of here!” a Black man shouted back.

The young man with the mic planted his feet and looked to his right and his left and reveled in the crossfire of the jeers and the cheers. “That’s what we’re talking about!” he said. “It’s time to fire Joe Biden!”

Hilario Deleon is the chair of the Republican Party of the county that’s about to host the Republican National Convention. His biography is in many ways a mishmash all his own, but he’s also representative of a larger, potentially politically pivotal group of non-college educated, underemployed, young and perhaps especially non-white young men who’ve responded so notably to former President Donald Trump’s populist appeals. He’s 23 years old. He’s half Mexican. He was adopted as a baby, has a white mother and a Black sister, and grew up on the south side of the county of Milwaukee — the highest concentration of Latinos in the state of Wisconsin. Deleon graduated from South Milwaukee High but opted not to go to college. He’s worked as a work-study student for We Energies, a parking lot attendant, a customer service rep on a boat on Lake Michigan, a waiter at an assisted living facility, a dishwasher at a pub that closed because of Covid and most recently on the staff at an indoor trampoline park in the suburbs until he quit earlier this summer. And after living on his own for a few years in a one-bedroom apartment and for a stretch in a house with his biological brother, he has moved back in with his adoptive mom. And maybe the quirkiest quirk of the Deleon mishmash: He’s been, for nearly a decade, an avid participant in Civil War reenactments.

But Deleon hasn’t just voted for Trump. He’s become very politically active in a very short period of time because of Trump. And he’s found himself in a county historically inhospitable to Republican candidates and ideas in at least a nominal position of authority that has enabled him to amplify the messages of Trump. Activated by Trump’s first run — he watched him come down the Trump Tower escalator the same month he finished middle school — Deleon was a local field organizer for the Trump campaign in 2020. That election was the first election in which he was old enough to vote. In 2021 and ’22, he was a staffer for the state GOP. And he just started a new paid post as a middle manager in Turning Point Action’s “ballot chasing army,” part of the sprawling right-wing group’s swing-state push. He believes the last election was “stolen,” he believes the events of Jan. 6 were exacerbated by “antifa,” and he believes the prosecutions of the former and maybe future president are tantamount to “political persecution,” he told me. And he believes, too, that if he can help get just a slightly higher share of Black voters, brown voters, young voters and “low-propensity” conservative voters to vote for Trump — if he can make Trump and other Republicans just “lose by less” in a place where they typically lose by lots — he can be a reason Trump wins back the White House.

“We increase our voter percentage even by a couple points … we win the state,” he said the first time we met. “I want to know that when I go to bed at night I feel like I’ve done enough every single day to try and make that difference.”

After spending a few days with him over the course of the last few weeks, it’s hard for me to pinpoint what precisely Deleon is doing to accomplish this — other than a more regular social media regimen and something he calls “Operation Connecting Milwaukee” that appears to entail somewhat scattershot door-knocking and ambient “relational organizing” of meeting and selling other people and convincing them to do the same. And by nearly any traditional measure — open, active offices, paid staffers, so on and so forth — Democrats here and the Biden campaign, too, make up the bigger, better-funded, better-organized operation. It’s true, too, though, that polling on the whole shows a heightened appeal Generation Z voters seem to have for Trump and the GOP, and granular data here in and around Milwaukee in particular in the last several cycles paint a pattern: The whiter the ward, the more Democratic margins have gone up — and the Blacker or browner the ward, the more those margins have gone down. The movement’s not much, but in a state in which the last two presidential elections were decided by scarcely more than 20,000 votes — Trump winning in 2016, Biden winning in 2020 — it doesn’t have to be.

And if nothing else, as whiter, wealthier and more educated voters here and elsewhere trend toward Democrats while a winning Republican coalition on all three of those fronts gets gradually less, an embodiment of these subtle but important, even decisive shifts in party preferences and allegiances might look a lot like Deleon.

That alone hasn’t necessarily made him a favorite of some more veteran party officials. “Hilario brings … something to the table,” Orlando Owens, the county party’s North Branch chair, told me diplomatically. “I don’t think it hurts to have Hilario there. He’s a little inexperienced,” he said. “Blending old with new isn’t always easy, the blending of multiple personalities — of having a person so young having a lot of authority.”

“We obviously are part of a party that is looking for young people to get involved in bulk,” said Brett Galaszewski, 27, Turning Point Action’s enterprise director and the county party’s first vice chair. “We’ve kind of adopted the mindset that now more than ever young people are needed to not just join the GOP but have a say and influence in it and to help lead it, and we kind of paved the way, I think,” he said.

South Milwaukee state Assemblymember Bob Donovan, who’s 68 and has been something of a mentor to Deleon, described a certain sort of inexperience as to some extent a plus. “Sometimes it’s easy to get set in your ways after serving a long time,” Donovan told me.

“I think Hilario’s doing a great job.”

Is he?

“Hilario would have to answer that question,” Cindy Werner, the county party’s second vice chair, told me.

Is he making new Republican voters? Is he, in other words, more making noise, or is he in fact making that difference he says he wants to make?

“I would be able to answer that question,” said Werner, “after the election.”

“TBD,” Galaszewski granted.

For now, as the Cudahy parade took a turn off Packard and headed toward its end, Deleon saw a water balloon thrown his way, saw plenty of middle fingers flashed in his direction, saw sour faces and thumbs theatrically thrust down. “Her body, her choice!” one man yelled. “We don’t need you!” But he also saw — and saw in an area that in 2020 gave Biden 54 percent of the vote — plenty of thumbs up and Let’s Go Brandon shirts and men and women and their kids jump up from their chairs and run toward the trailer and clamor for the signs that said Trump.

“That,” he told me, “was the most support I’ve ever seen come out of Cudahy.” And on the way to the next parade, still standing on the back bumper and clearly buzzing from the experience he described as “a blast,” Deleon busted out a quite credible Trump impression. “Always good to see you out here in Cudahy, folks. We’re going to get this place winning again,” he said on the mic in his best Trump drone. “I just want to say Cudahy is one of the greatest cities there is in Milwaukee County, and I look forward to seeing you all, here in Milwaukee, for the Republican National Convention …”

‘Might as well try out politics’

He was born Nov. 25, 2000, to a man named Miguel and a woman named Michelle. Linda Deleon had tried to have kids but couldn’t and signed up to foster. At 4 in the morning on April 2, 2001, she got a call from social services. They were allowed to say only so much, and she heard more only later. “They fought,” she said. “There was violence,” she said. “So they brought him,” she told me. “I had to go to Walmart to buy bottles.” Her husband at the time ran three bars and drank too much, and at 38, in October of 2006, he killed himself. Hilario, the oldest of the three children he and his wife had adopted, was 5 — old enough to still today remember seeing his adoptive father in his suit in his casket. His biological father had moved back to Texas, but his biological mother was still around, and Hilario now wanted to know her. So Linda took him for occasional visits, which often were painful and awkward, she recalled. “She goes, ‘I don’t know what to say to him.’ I said, ‘Ask him what he likes, ask him what color he likes, ask him what food he likes …’” The infrequent get-togethers got more and more infrequent, and in August of 2013, in a room in a Rodeway Inn, Michelle died of a drug overdose.

Hilario wasn’t especially attentive in school, but he grew from a young age to love the Civil War. Linda had taken him to the historic site in Greenbush, Wisconsin, called the Wade House, where there was a small reenactment. “And he goes, ‘That really happened?’” she told me. “‘We fought against our brothers? Against our families?’” She gave him two hardbound volumes of The American Heritage Picture History of the Civil War, and he spent hours and hours studying their pages, watching Glory, Gettysburg and Lincoln and everything he could look up on YouTube. In June of 2015, for a ceremony at a cemetery filled with Civil War dead that was not far from his house, he walked over and saw a man named Wayne Issleb dressed as Gen. Ulysses S. Grant.

“There he was with his mom,” Issleb, who lives in Kenosha and manages a motel, told me, “and he approached me …”

“I was a little nervous,” Hilario told me, “but I asked him, ‘May I join you guys?’”

“And I said, ‘Well, absolutely,’” Issleb said. “And he knew the Civil War inside and out — dates, generals, battle times. I mean, he’d really done his research …”

And over the ensuing several summers, Hilario Deleon went with Issleb to dozens of reenactments, in Ohio and Iowa and Illinois, in Pennsylvania, Georgia and Tennessee.

He took to calling him Papa.

And the same month he started getting to know Issleb in person, he started to get to know Trump on TV. He’d never watched The Apprentice. He knew Trump, he told me, mainly from his cameo in Home Alone 2. There, though, the man was, coming down that escalator in this building that bore his name, along with his wife and adult children. “A beautiful family,” thought 14-year-old Deleon. At the first high school he went to, a Jesuit school with a mostly Latino enrollment, he got teased for his open affinity for Trump. His classmates, he said, called Trump a bigot, a racist and worse. It made him double down. Even so, though, he didn’t really get involved in politics until after he graduated from South Milwaukee in 2019 — and after he lost the job at the assisted living facility that fall, and his girlfriend broke up with him, and the engine of his 1992 Honda gave out, and he was on his own in his apartment and struggling to pay his bills. And then the pandemic happened, and he lost the dishwasher job. “I was angry,” he told me. “And I literally said to myself, ‘Well, shit, I got a lot of free time on my hands now — might as well try out politics!’”

He showed up unannounced in the summer of 2020 at the state party office in Milwaukee on Martin Luther King Jr. Drive. He had with him a three-ring binder filled with his plans to put on a rally to counterprotest the Democratic National Convention scheduled to be held in the city that summer. “All of a sudden, this young kid comes in and goes, ‘I want to help Donald Trump get elected, I want to do a rally for Trump,’” party volunteer Bruce Boll told me. “And I slow him down, and I say, ‘Hilario, take a breath.’” His rally never happened, partly for the same Covid-related reasons the DNC didn’t, but Deleon kept showing up at dinners and picnics and meetings and offices. He helped organize an event at which people set fire to masks. He got hired on at a local lower rung of the Trump campaign. He turned that gig into the gig with the state party. He turned that into a role as a driver and a gopher for Donovan’s unsuccessful mayoral campaign. And he got himself appointed as the RPMC’s second vice chair after the sitting second vice chair passed away. And at the beginning of 2023 — at barely 22 — he decided to run for the top spot. Deleon had a five-year plan he pitched, but his narrow, multi-ballot election by the county caucus was as much a function of friction between the half-dozen fiefdoms that make up the party in Milwaukee.

“I understand many people are eager to move forward and help build this County Party into a proper political organization,” he wrote in the “Chairman’s Report” in the newsletter he rechristened “The Milwaukee Mammoth.”

“I have been working overtime with the Executive board to help fulfill our role in one of the most important movements the world has ever known.”

By this past January he was at Turning Point’s Restoring National Confidence Summit in Las Vegas. “Hilario Deleon, chairman of the Republican Party of Milwaukee County,” he said, introducing himself, standing at a mic in the crowd. Charlie Kirk, the organization’s contentious founder and president, stood on the stage. “Wow,” said Kirk.

“What was your name again?”

“Hilario Deleon.”

He asked a question about the possibility of using “conservative influencers” to highlight “the phenomenal work” being done by county “chairs from across the country.”

Kirk didn’t really answer the question. He zeroed in on something else. “So what you are doing in Milwaukee might actually end up saving the entire civilization,” Kirk told Deleon. “If we lose by less in Milwaukee, we could win the White House,” he said. “If we lose less by 2 percent, what could that mean — a hundred thousand votes? — which could make the entire difference,” Kirk continued. “I can’t encourage you enough as a Gen Z county chair in one of the most important counties …”

“Thank you so much, Charlie,” Deleon said. “Let’s go kick some ass!”

“I’m told I have a lot of big eyes watching me,” he told me earnestly late last month at a pancake house here — three days after he’d met Trump for the first time at his rally in Racine.

“Is that right?” I said.

“That’s what I’ve been told.”

“And who’s telling you that?”

“People that are kind of higher up.”

“Does that make you nervous?” I asked. “Are you feeling some pressure?”

“There is a lot of pressure, and I am nervous,” he said. “Because I know what happens here in Milwaukee will decide the fate of this country.”

“Let me ask you one more thing,” I said as he got a go-box for the rest of his steak and scrambled eggs. “You’re a person who knows more than most about the Civil War. Do you think we’re headed toward another civil war?”

“I think we’re in a cold civil war,” he said, “right now.”

‘He really doesn’t know what to do’

“War,” he said one recent day at the county party’s main office in West Allis, “is the final signal that we as a species have failed — to be able to talk our issues out, discuss, debate.”

On his desk were the pair of American Heritage books that ignited his interest in the matter. War, yes, but civil war — that’s a failure, I suggested, not just as a species but as a nation. I asked him about Jan. 6 and the attack on the Capitol. “Most of the people were there peacefully protesting, and they just got caught in the middle of what was going on,” he said, alluding to antifa and what he believes were other bad-faith, false-flag pot-stirrers. “It’s easy to go buy a MAGA hat and dress up.” I asked the proud “Union boy” in his many reenactments what he thought of the people who brought to the seat of the United States government battle flags of the Confederacy. “They’re stupid,” he said. “You go to most if not all Trump supporters’ houses, and there’s an American flag outside.”

This conversation, its location, his position — they all underscored the reality that Deleon is no longer simply a student of internecine strife. He’s a participant. The country careening toward this fall is on a razor’s edge. Wisconsin, which conceivably could decide the election, basically couldn’t be more closely divided. “Literally every ward and every nook and cranny of this county could make the difference,” Galaszewski, the first vice chair, told me. “When people ask me who I think will win,” Marquette University pollster Charles Franklin said, “I say, ‘Give me a quarter, and I’ll flip it.’” And the biggest, most tightly contested, most consequential battles, as any reader of history well knows, can and often do turn on the smallest of decisions — on minor characters, even, whose actions end up having not-so-minor ramifications.

Deleon sat at a table in the office with three volunteers 30 to 40 years his senior. A man named Rich. A man named Herb. Bruce Boll. Deleon, who likes to draw and considers himself an artist, showed me some logos he had designed — a Latino Coalition logo, a Black Republican Coalition logo, an Operation Connecting Milwaukee logo. He clicked through a mock-up of a new website for the county party he hopes to have operational by the start of the national convention. “It needed a reboot,” he told me. Rich was trying to log on to a video conference with the company hosting the site but couldn’t seem to get the sound to work. “Hello?” Rich said. “Hello? Hello?” A couple of walk-ins wanted signs. They were voters already, diehard Republicans, but Deleon persuaded them to become dues-paying members as well.

“I want people to know what’s going on. I want them to see the work that we’re doing here in Milwaukee,” he told me. “I really think that Milwaukee County, the Republican Party of Milwaukee County, is going to become the flagship of the Republican armada in this state.”

Of late Deleon’s been doing interviews with local, national and international press. He’s been manning the county party’s tables and booths at Milwaukee’s events for Juneteenth, for National Puerto Rican Day, for Polish Fest. Earlier this year, the party co-hosted as a speaker Tulsi Gabbard. Last year, Kari Lake was a guest. When the jury in New York found Trump guilty of falsifying business records to cover up a payoff to a porn star, Deleon on his social media accounts called the verdict not just “political persecution” but “ELECTION INTERFERENCE!!!!”

As for more specific get-out-the-vote initiatives? “President Trump has talked about that at his rallies, and I’ve been talking about it for a long time now. We have to build a coalition of disaffected liberals, independents, libertarians and Republicans,” he told me. “So we’re going to be making sure that we’re going to knock on those people’s doors,” he said.

“I guarantee that you will see some sort of increase in Milwaukee County.”

Some of his own people — fellow party officials, longtime party activists — are some of his biggest skeptics. “In all honesty, Hilario’s a great guy, but he’s tied into Turning Point,” Sam Hagedorn, a former county party chair and the father of a current state supreme court justice, told me, “and I think Turning Point turns people off.” Many party stalwarts, citing defeats in, say, key races in places like Michigan and Arizona, wonder if Turning Point’s turnout efforts actually yield the results to win.

Lose by less? “That terminology is not the terminology I’m looking for. That’s a very defeatist position,” said Owens, who has his own initiative called Project Move the Needle to try to garner a bigger share of Black votes on the north side of the city. “I don’t use that jargon,” Owens said. “I look at moving the needle.”

“I like the kid, but the problem is he has no following, he has no base, and he really doesn’t know what to do,” said Bob Dohnal, another former county party chair and the publisher of the Wisconsin Conservative Digest. “He’s well-intentioned, he’s part of the future of the party, but I’ll tell you: When I was 23, and I’m a lot smarter than Hilario politically, I knew practically nothing.”

Even so, the south side of Milwaukee County, where Deleon was born, where he grew up and where he still lives — it’s the bottom quarter of the county that’s represented in Congress by Janesville-based Republican House member Bryan Steil, and Steil sees opportunity, he told me. “Those communities are wildly open to hearing a conservative message,” he said when I ran into him on the Fourth of July after the Cudahy parade and before the start of the parade in neighboring St. Francis. “In each of these municipalities, you’ll see the trend line, and you’ll see where we’re capable of taking these communities.”

Just ahead of Steil in the parade in St. Francis was Deleon. The Ford Expedition and the trailer with the hay bales was on the move again, and he was back on the back bumper and back on the mic, telling people to go vote on Nov. 5, telling them to vote for Trump, telling them to save the country — when he spotted a woman holding a simple sign. “Peace, Love and Democracy,” it said in Sharpie script.

“Ma’am, I just want to correct your sign. I’m going to correct your sign,” he said, the speaker rigged up on the roof of the SUV amplifying a sort of pedantic, sanctimonious tone geared less to have a conversation and more to piss a person off. “We are,” he told her, “a constitutional federal republic, not a democracy.”

And then this woman did something she would tell me she had never done. She stopped watching the parade and she joined it. She put herself between the rear of a convertible with waving local teen beauty pageant winners and the front of the Expedition and the hay bales. And she held up her sign, and she started walking, and she didn’t stop.

I sped up to talk to her. “I just need to do something,” Chris Korenak, 63, told me. “I was just going to stand on the sidewalk …”

I asked her about the state of the words on her sign. “How are you feeling,” I said, “about peace, love and democracy right now?”

“Very unstable,” she said. “Very fragile.”

Korenak with her sign saw off to one side a woman with a shirt. “Trump 2024,” the shirt said. “THIS TIME IT’S PERSONAL.”

I thanked Korenak for her time and went back to talk to Kathy Kuhn. She told me she was wearing her shirt because she was sick of the way people had been treating her because of the signs in her yard. Her Trump signs. Her MAGA signs. Her “Fuck Joe Biden” sign. “They’ve thrown shit on my lawn. They’ve let their dogs shit on my lawn. This time,” she said, “it is personal.”

It was the 248th anniversary of the independence of this country. After the parades, driving Deleon back to his car, the sights and sounds of this particular Fourth of July playing in my mind and ringing in my ears, I asked him again about the possibility in this country of a second civil war.

“There’s really no shots that have been fired at this point, but tensions are high,” he said.

“But even if a civil war were to break out, I don’t know if the entire country would be dragged into it,” he said.

“It’s hard — there’s no North and South anymore,” he said. “I think it becomes a true neighbor-against-neighbor kind of mentality.”

Kathy and Chris in St. Francis. The people in Cudahy on one side of the street yelling at the people on the other with the 23-year-old chair of the Republican Party of Milwaukee County in the middle on the mic back by the Packard Avenue bars.

“Now,” Deleon asked out loud, “are people willing to pull out guns and kill their neighbor? I don’t think so. I think people say a lot of things like that all the time. But in my opinion, I think it’s just talk. I don’t think there’s enough crazy people that are willing to go and do that.”

In Milwaukee, around the county, around the country, the fireworks were about to start for real. But at least for now in the car it was quiet.

“I sure hope there isn’t,” he said.

AP TROIB News