Tim Alberta is a national political reporter at Politico Magazine.

GREENVILLE, Wis. — Kevin Nicholson has a confession to make, if only someone would listen. Standing on a makeshift stage inside a burgundy-colored barn rented by the Republican Party of Outagamie County—two hours north of Milwaukee, just west of Green Bay—the U.S. Senate candidate and unlikely new object of conservative fascination has broken into a biographical speech. But many attendees don’t seem to care. He isn’t unique in receiving this treatment; the audience, buzzing off plates of barbecue and $2 cans of Miller Lite, was just as irreverent toward their own congressman, Mike Gallagher, as well as Leah Vukmir, a state senator and Nicholson’s rival in the Republican primary. With the barn’s metal gates flung upward to welcome August’s evening breath, and clusters of party loyalists chattering in buffet lines and around red-plastic-draped picnic tables, the acoustics are dreadful for a rookie politician hoping to be heard.

But then it happens: Nicholson, a decorated combat veteran and business wunderkind with advanced degrees from Harvard and Dartmouth, begins taming the crowd, one expertly crafted anecdote at a time. He recalls his experience fighting and losing friends in Iraq, as Democrats “lied” about the gains his Marines made. He tells of adventures in academia, where he could “test the assumptions of the elites and the experts to find out what they really don’t know.” He mentions his time as a McKinsey consultant, engineering corporate restructurings around the world, as a segue to denouncing the “garbage” math in Washington on the sustainability of America’s debt. The longer he goes, the quieter his audience gets.


Nicholson arrived here a virtual unknown; the strapping, clean-shaven 39-year-old, with light blue eyes and a wavy dark mane, lingered awkwardly near tables to present himself. But as he concludes his remarks, attendees begin approaching the podium. The first one there is Jack Voight, a former state treasurer who recently retired from local office and promised his wife he wouldn’t go near another campaign. Voight engages Nicholson in a passionate, minutelong dialogue, the two men gripping each others’ hands in an arm-wrestling stance. Voight gives the candidate his phone number and tells him to call tomorrow. “I know where all the bodies are buried,” Voight tells him, grinning. Just like that, Nicholson has gained an influential ally.

This is becoming routine. Since declaring his candidacy in late July, Nicholson has won the endorsement of the Club for Growth, the influential and well-heeled conservative group; secured the backing of former United Nations Ambassador John Bolton and his affiliated PAC; and assembled an impressive roster of wealthy Republicans to helm his campaign’s financial operation. Most important is the support Nicholson won before entering the race: Richard and Elizabeth Uihlein, titans in the conservative donor universe, parked $3.5 million in a super PAC for him, baffling rivals in both parties and lending the little-known, first-time candidate instant viability.

It’s rare—practically unheard of—for an established donor to spend that kind of money on an unproven commodity. Then again, candidates like Kevin Nicholson don’t come around every day. It should come as no shock that some Republicans have fallen for him: With his Hollywood looks, military pedigree, Ivy League smarts and private-sector proficiency, Nicholson could have been built in a GOP laboratory. He is hungry and confident and committed, having oriented much of his adult life around an eventual run for public office. His published writings on pension reform read like a product of the Heritage Foundation; his voluntary second tour overseas is the stuff ad-makers fantasize about. He is, for comparison’s sake, a wealthier, better-looking and more charming version of Senator Tom Cotton. “Kevin is even more impressive in person than he is on paper,” gushes David McIntosh, the former congressman and Club for Growth president.

Kevin Nicholson in his home office in Pewaukee, Wisconsin. | Darren Hauck for Politico Magazine

The spell Nicholson has cast over a number of influential Republicans is a source of wonder in Wisconsin these days. Yet people who know him say the explanation isn’t terribly complicated. “He’s a McKinsey consultant. His job is to walk in a room of powerful, wealthy people, blow them away, and get their money,” says one state official who is friendly with Nicholson but obligated to remain neutral in the race. “And he’s very, very good at it.” Another person who spoke on condition of anonymity—a longtime friend of Nicholson’s who is a Democrat, and therefore loath to either hurt or help him with an on-record statement—says none of Nicholson’s early success is surprising. “I’m guessing once he managed somehow to get in front of Dick Uihlein, he just impressed the shit out of him. I’m sure he laid out the case and convinced them he could make it happen,” the friend says. “I’ve seen it—the guy’s fucking incredible. Nobody knows him, and he’s arguably the front-runner for the nomination for U.S. Senate.”

But there’s a glaring flaw in his otherwise immaculate résumé: Kevin Nicholson hasn’t always been a Republican. He was once an aspiring politician and rising star—in the Democratic Party.



***

In 1999, Nicholson, a junior at the University of Minnesota, won an upset victory to become president of the College Democrats of America. The trappings included a full-time position at the Democratic National Committee in Washington and a speaking slot at the party’s 2000 convention. The archived C-SPAN clip of Nicholson’s nearly three-minute speech—in which he declares, “We care about a woman’s right to choose”—is emblematic of the minefield he must navigate en route to the Republican nomination, much less a general election victory. His high-profile stint as a Democrat, followed by what is better described as an evolution rather than a road-to-Damascus conversion, offers lip-licking openings for opponents to question his credibility, consistency and character. What has turned up so far—a laudatory letter he penned in 2000 to the pro-abortion group EMILY’s List; questions about his voting record in the 2008 primary; personal attacks from his former college roommate—are the political equivalent of body blows. Democrats, fearful of losing Tammy Baldwin’s seat in a state President Donald Trump carried last fall, are actively searching for a knockout, having built an atypically large opposition-research effort in hopes of derailing Nicholson before his campaign picks up steam.

He understands the scope of the dirt-digging—with former friends, colleagues and even roommates teaming up to take him down—and therefore seizes every occasion to talk about his past. The goal is to inoculate his candidacy in the hopes that voters will view attacks on his college activism as old news. But his strategy is not merely a defensive one. Nicholson knows that Wisconsin’s Republican base is comprised of many white, working-class voters who were Democrats themselves not a generation ago; the objective in playing up his Democratic roots is to turn a potentially crippling liability into his campaign’s unlikeliest asset. “It’s something I’ve embraced,” he tells me, riding north on I-43 toward Greenville in the back row of his family’s black SUV. “I start every speech talking about how I was a Democrat, and what I saw and what I was involved in, and how it made me a conservative.”



Just like Ronald Reagan,” Voight tells me. “He has seen the other side.”



Sure enough, within the hour, Nicholson opens his remarks to the Outagamie County GOP by disclosing his collegiate party affiliation. It draws a few playful boos, but then again, most people aren’t listening yet. Jack Voight is. After his passionate exchange with Nicholson following the speech, I ask Voight to explain his enthusiasm for the GOP newcomer. “Just like Ronald Reagan,” Voight tells me. “He has seen the other side.”

It’s not the first time I’ve heard Nicholson mentioned in the same breath as a president. Progressives that loathe (and fear) him claim there’s a master plan to pursue the White House, while conservatives he has courted describe someone who, to borrow from Bruce Springsteen, was born to run. “He is sort of the central-casting version of what a Republican candidate should look like, be like, sound like,” says Charlie Sykes, the once-dominant conservative talk-radio voice in Wisconsin who recently quit to write an anti-Trump book. Despite long being Vukmir’s biggest booster in the state’s conservative media scene, Sykes, who’s staying neutral for the time being, says of Nicholson, “If voters are looking for a fresh face, he would be the ideal.”

Months of gossip percolating through Wisconsin’s political class have produced two distinct and diverging judgments of Nicholson, revolving around the sincerity of his conversion and the scope of his ambition. The generous view holds, more or less, that Nicholson quit politics because he felt abandoned by the Democratic Party, discovered his inner conservatism and re-emerged serendipitously back home just as Wisconsin’s GOP bench was growing a bit stale. The cynical view is essentially that Nicholson has wanted to be president since he was a teenager and has few core convictions; that he saw the demographic winds shift during his time in D.C. and decided the clearest path to public office as a straight, white man in Wisconsin would be as a Republican.

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After conversations with more than two dozen people who know Nicholson, I’ve concluded that there’s something to both of these narratives. Friend and foe alike testify in detail to his methodical preparation and deep-seated political aspirations, leaving no illusion that he finds himself running for federal office by happenstance. And yet it’s apparent that Nicholson, a moderate Democrat turned Marine officer, felt fundamentally betrayed by modern liberalism and went searching for something else. Neither of these broad conclusions would seem inherently harmful to Nicholson; it’s the details that could complicate his tightly crafted story of political self-discovery. Any date that proves inconsistent, any record that contradicts past statements, will fuel the perception of a candidate with something to hide. It’s a perception Nicholson, an intensely personal guy who is introverted by nature, plays into; his campaign would not tell me, for instance, what Nicholson’s parents do for a living. This is likely because he hails from a heavily Democratic family—his mother, Federal Election Commision records show, donated thousands of dollars to liberal candidates and causes in recent years—and wants to protect his parents from efforts to expose intrafamily tension. Yet his guarded nature adds to a shadowy aura surrounding his campaign, which, paired with imminent attacks on the discrepancies in his biography, could prove debilitating. The Republican Party’s next big star might not even pass his first test.

It’s risky to start poking holes in a decorated veteran’s backstory, and Nicholson’s GOP adversaries have no need to get overly personal—at least, not yet. They believe, in a state where Republicans have radically transformed government through seven years of brutal party-line warfare, that Nicholson’s new-to-the-team routine won’t fly with voters. Wisconsin is one state where there is little daylight between the grass roots and establishment; outsider rhetoric can be ineffective bordering on counterproductive. Against that backdrop, Nicholson’s early traction has some Republicans concerned, if a bit annoyed.

When Vukmir learns that I’m here to write about Nicholson, she rolls her eyes. “What do you know about him?” I ask. She shakes her head. “What you’ve heard him say. That’s about all I know.” Vukmir, who sits on the powerful Joint Finance Committee, was waiting for the state’s budget to pass before officially announcing her Senate campaign, but couldn’t afford to wait any longer and wound up launching in the first week of September. But I know, speaking to her in Greenville weeks earlier, she’s here for the same reason as Nicholson. During our interview, Voight comes around the corner—and Vukmir buttonholes him. They make a minute of small talk before Vukmir gets to the point: “I’ll be calling you.” Voight shoots me a glance, wondering if I’ve spilled the beans about his bromance with Nicholson. “OK,” he smiles guiltily.

I can’t tell whether Vukmir sees through Voight. But it’s apparent, after another minute of prodding her about Nicholson, that she’s struggling to mask her irritation. “I don’t know what Kevin’s conservative record is, other than him saying he’s a conservative,” Vukmir says. “So he’ll have to get people to believe that.”



***

The story of Nicholson’s transformation starts with Jessie Roos. They met at the University of Minnesota, and according to mutual friends, forged a relationship owing to equal parts romance, intellectual admiration and political drive. They were inseparable, with Roos pulling double-duty as Nicholson’s girlfriend and most trusted adviser. This arrangement caused uneasiness in College Democrat circles as Nicholson campaigned to lead the national organization. The reason: Roos was among the most prominent conservatives on campus. In 1998, she and four other students were plaintiffs in a lawsuit against the university; they objected, the Associated Press reported at the time, “to sending $1.04 per quarter in mandatory student fees to the Queer Student Cultural Center, La Raza Student Cultural Center and University-YW (Young Women), groups they say promote homosexuality, communism and abortion.”

Despite their diverging politics, Roos was Nicholson’s “north star,” a phrase used by two separate college friends to describe her influence over him. The couple broke up and reconciled repeatedly, in part because Roos feared Nicholson might never acknowledge the truth about himself: that deep down, he was a conservative. The relationship nearly ended, permanently, when Nicholson advocated “a woman’s right to choose” in his convention speech. Reviewing the text with him by phone from Minnesota, Roos went ballistic when she heard the line and demanded Nicholson remove it. He refused. “We got in a fight. I knew at the time it was not something he had thought extensively about,” she recalls to me. “And that definitely was a piece of the conversation in terms of courtship and leading toward marriage, because that was a no-go zone for me.”

Kevin and Jessie Nicholson have been a couple since college. The story of their relationship is the story of Nicholson’s transformation. | Courtesy Kevin Nicholson

Today they can claim a happy ending: Nicholson ultimately turned anti-abortion, the couple got married, had three children and are now simpatico in their worldviews. Jessie Roos is now Jessie Nicholson, herself a political pro with a communications background: She was a George W. Bush political appointee at the Department of Agriculture and previously worked for former Minnesota Gov. Tim Pawlenty as well as Republicans in the Statehouse. It takes five minutes around the Nicholsons to realize that Jessie, who led her husband’s conversion, will be guiding his Senate campaign more than any consultant or strategist. “We are partners, and we both have different roles to play,” she says, smiling. “I know how I think things should go.”

She’ll have to help her husband craft sharper answers to questions about his background, including that convention speech. Before heading to Wisconsin, I heard Nicholson say on multiple radio shows that someone “put a piece of paper in front of me” containing the abortion rights language. As we ride together, I ask a simple question: Did you write that line, or was it written for you? “Um, let’s start with the most important thing,” he replies. “I’m responsible because I said it. So don’t think that I’m equivocating on this.” Sure, I say, but it’s important to nail down: Did you write it? “Yeah—so, no. The bottom line is ... ” Nicholson stops and swallows hard. His face is flushed. “Cognizant of the fact you’re going to write this out, I want to be clear: I own it, ‘cause I was a young person but I was an adult, and I should have known better. Period.” He continues: “I wrote a speech which was pretty innocuous. It was about generational differences. ... That was sent to the DNC, it was recut, and that particular phrase was inserted.” So, I ask him, you didn’t write that phrase about abortion? “Nope. Well it—don’t get me as a bullshitter here. I own it. I said it.”

Unless the DNC is hanging on to 17-year-old emails containing Nicholson’s original draft, nobody can prove who wrote that line. But Nicholson’s convoluted story only invites further scrutiny of his record on abortion. Already, Democrats have released the EMILY’s List letter, as well as the College Democrats’ abortion rights platform that was adopted on Nicholson’s watch. I found something else, having heard from friends about his frequent appearances on MSNBC during the 2000 campaign: a transcript of “Equal Time,” on July 14, 2000, in which Nicholson debated Scott Stewart, then the chairman of the College Republicans. Discussing the Supreme Court, 22-year-old Nicholson said, “Obviously, the next president is going to have a huge impact on the court. And I personally believe, and the people in my organization, the College Democrats of America, believe that Al Gore needs to be elected in order to ensure that the simple issues, base issues like a woman’s right to choose, must be protected.”

I couldn’t find the videotape. But Nicholson’s opponents probably will, and if they do, he can expect a bruising attack ad highlighting his abortion flip-flop. Whether voters care about what a candidate said in college remains to be seen—Trump called himself “very pro choice” on Meet the Press in 1999 and the GOP nominated him 18 years later—but Nicholson’s vulnerability speaks to the broader challenge he faces in running his first race as a Republican, with his only political experience coming as a Democrat.

Two things are striking as it relates to Nicholson and abortion. First, it represents a rare policy area in which his opponents have discovered vulnerability; one Democrat familiar with the party’s opposition-research efforts tells me they are frustrated because of how careful he was in college to avoid taking polarizing positions. And second, Nicholson’s liberal friends—most of whom insisted they not be quoted in this story—agree that his change of heart on abortion comes across as the most authentic element of his entire conversion. “I have children, and they’re a hell of a lot more than a choice,” Nicholson tells me. “I also saw innocent lives of kids [taken] in combat. I say that and it’s not hyperbole, it’s not a joke. If anything makes you stop and think about how wasteful it all is, it’s watching life get blown to smithereens because they’re in the wrong place in the wrong time. It does change your perspective, and it does mature you.”



***

Before he met his wife, Nicholson told me, his “greatest political influence” was his grandfather, a 50-year union worker and FDR devotee, who drilled into his grandson’s psyche the evils of Ronald Reagan and the Republican Party. Nicholson says those spirited discussions with the man he spent his childhood weekends with—and eulogized in early 2016—formed the core of his worldview as he headed off to college, and inspired him to become active in the Democratic Party.

It certainly sounds improbable: a teenager stumbling into campus politics, informed by little more than his grandfather’s New Deal nostalgia, and within a few years ascending to lead the College Democrats of America. Hoping to better understand Nicholson’s background, I went to his hometown of Mequon, Wisconsin, and visited his alma mater, Homestead High School. To my surprise, few people there remembered him. He flashed serious wheels as a track-and-field standout, and earned good grades, but there was zero extracurricular activity to foreshadow a career in politics—no student government, honor society, study abroad. When I talked with two of the Social Studies department’s longest-tenured teachers—Ernie Millard and Steve O’Brien, both of whom taught when Nicholson was there—neither could muster a memory. Only after I showed Millard his photo did he remember coaching Nicholson on the freshman wrestling team. When I told them he’s running for U.S. Senate, O’Brien leaned forward. “You’re shitting me.”

The portrait of young Nicholson, painted by the few who knew him then, is of a reserved kid who was both smart and standoffish. (“I like long walks,” reads the caption beneath his senior yearbook portrait, “especially when they are taken by people who annoy me.”) His political activism was mostly limited to lunch-hour debates with friends. One such discussion was captured on video when Nicholson’s friend, Ryan Rudominer—who later became a Democratic operative in D.C.—won a C-SPAN scholarship as a high school senior. The footage opens with Nicholson arguing to friends that “Welfare is the only program designed to get people off of it,” adding, “You do not want generations on welfare.” (This was 1996, and Nicholson idolized Bill Clinton’s brand of center-left politics.) The biggest difference between Nicholson in high school and college may have been his surroundings; Rudominer says they were two of the only Democratic students in their staunchly conservative town, and that Nicholson hadn’t yet come out of his shell. “It didn’t surprise me to see Kevin running for national political office,” Rudominer tells me. “He’s always had the political skills and ambition for it.”

On a makeshift stage, Kevin Nicholson speaks to voters in Outagamie county in northern Wisconsin. | Tim Alberta

Everything changed when Nicholson arrived on the ultraliberal Minnesota campus. Within a year he was elected to student government—he would eventually run, unsuccessfully, for student body president—and promising his new friends that some day he would win the White House. More than ever, Nicholson kept his guard up; he was careful, friends tell me, never to be seen drunk or heard cursing in public. But his ambition was obvious to all: Nicholson ordered a vanity plate that read “ARFS1” (short for “Air Force Once”) and, after establishing himself as the top Democrat on campus, set his sights on winning the presidency of the College Democrats of America.

His closest ally was Mike Tate, who led the Wisconsin College Democrats and later served as chairman of the Wisconsin Democratic Party during Baldwin’s victorious Senate run in 2012. Nicholson enlisted Tate’s support when running in college and the two became fast friends, having grown up 12 miles apart in suburban Milwaukee. They roomed together at the 2000 convention and Tate often crashed at Nicholson’s place in D.C. “He had his whole life planned out. He was going to serve in the military, come back to Wisconsin and run for office,” Tate says. “My biggest disappointment is that he’s doing it as a Republican.” He tells me Nicholson “gets up every day with a mission” and “should absolutely be taken seriously” by Democrats, even if Tate still doesn’t understand why his friend switched parties. He recalls one late-night college conversation that he can’t shake. “I was once foolish enough to think I wanted to run for office, and he talked to me about how Humphrey and Mondale were partners in Minnesota politics for decades,” Tate says. “And he said, ‘Mike, that could be you and me in Wisconsin.’”



He had his whole life planned out. He was going to serve in the military, come back to Wisconsin and run for office,” Tate says. “My biggest disappointment is that he’s doing it as a Republican.”



Nicholson today is embarrassed by his former self, telling me three times that he was a “punk kid.” This is precisely how some fellow College Democrats remember him: as the cold, cocky, unpopular leader of their organization. “I did not like Kevin, and he would be the first person to tell you that,” says Alexandra Acker-Lyons, who was Nicholson’s vice president and is today a Democratic consultant. “Kevin is that guy—D.C. is crawling with them, summer interns and Hill staffers—who you know wants to run for office, and you know isn’t doing it for the right reasons.”

Others followed him with a cult-like fervor. “He was very well liked and could really relate to people, talk to them on their level,” recalls Kevin Pomasl, an active Democrat on Minnesota’s campus who worked local races and became Nicholson’s close friend. Pomasl, who today runs a fire equipment company in northern Wisconsin and considers himself an independent, says Nicholson “sold himself” as a star-in-the-making, and people gravitated toward him accordingly. One such person was Adam Tillotson, who was a year behind Nicholson at Minnesota and met him through College Democrats. Drawn to his “powerful personality,” Tillotson says he became Nicholson’s friend and political disciple. “There were so many people who saw great things in him,” Tillotson tells me. The two rented an apartment together near campus, but soon had a falling out. Tillotson packed his bags. They never reconciled, and Tillotson—who today leads a teachers union and makes no bones about being a partisan—is now Nicholson’s fiercest critic, bombarding Wisconsin reporters with tales of the Senate hopeful’s zealous pursuit of the Oval Office. Among many other accusations, Tillotson says Nicholson was verbally and emotionally abusive toward people during college. Nicholson, visibly irritated by questions about his former roommate’s scattershot allegations, tells me through a clenched jaw, “He’s lying.” Notably, in interviews with five other people who knew Nicholson at Minnesota—including three Democrats who oppose his Senate candidacy—nobody corroborated those accusations.

Nicholson took a semester off school to work at the DNC while leading the College Democrats, during which time he told everyone of his plan to join the Marines after graduation. In retrospect, Nicholson says, the wide-eyed reactions were an early indication that, “This wasn’t my crowd.” But there were other signs Nicholson didn’t belong; for a straight, white, centrist Democrat from Wisconsin, the party’s embrace of what he calls “identity politics”—and its leftward lurch on cultural issues at the turn of the century—made him uncomfortable.

“He was struggling with it back then. I remember teasing him and joking that he was going to end up as a Republican,” says Stewart, the former college GOP chairman who was Nicholson’s frequent sparring partner on cable television. Stewart hadn’t spoken with Nicholson in years, but says he wasn’t a bit surprised to learn that his old adversary had switched sides. “We’d be in the green room, talking about our families, and as we talked he would reveal these misgivings about the Democratic Party,” Stewart recalls. “I always got the impression it was something he was dealing with.”

When Nicholson returned to Minnesota in the fall of 2000, he slowly steered away from campus politics. He took over as president of the student newspaper, wanting to pad his résumé with business experience, and began closing in on graduation. But he grew restless and abruptly left school again—this time, to work as a ranch hand in rural Wyoming. He told friends he needed to “figure shit out,” which nobody except Jessie understood. “He had this weird, early life crisis,” Tate tells me. For the next year and change, Nicholson was off the grid, communicating only with Jessie and a few close friends via handwritten letters, telling them of books he was reading and things he was learning about himself. By the time he returned in late 2002 to finish up his coursework, something was different about Nicholson. The guy who once had it all figured out, only to begin drifting, now had it all figured out again. He graduated the next spring, married Jessie and joined the United States Marines Corps.



***

Nobody at Camp Lejeune knew much about Nicholson in late 2005, except that he was the new guy joining the 2nd Combat Engineer Battalion—and that a torn ACL in his left knee had delayed his arrival. (Nicholson has torn the same ACL three times.) It took nearly a year for Patrick Cleary, a fellow second lieutenant in the battalion who quickly became Nicholson’s closest buddy on the base, to discover a secret. During a discussion at the officers’ club of a new book, The Audacity of Hope, by Illinois senator and likely presidential candidate Barack Obama, Nicholson exploded. “What a bunch of bullshit. We’re just going to change the world with hope?” he said, according to Cleary. “Why don’t we just tell our Marines we’re going to war with hope?” Cleary says the officers exchanged puzzled looks. “‘Why are you so worked up?” Cleary asked. “He said, ‘I used to be the president of the College Democrats and I believed in this shit!’” Cleary recalls. He re-enacts his response, cocking his head to the side: “Whaaaat?”

By his telling, Nicholson had been moving rightward since his stint at the DNC in college, but it was the tour in Iraq when he had “given up on any shred of, ‘I’ll be a different kind of Democrat.’” | Courtesy of Kevin Nicholson

It was a similar story the next year during Nicholson’s 2007 deployment to Iraq. Leading 37 Marines in Anbar Province, on the heels of President Bush’s troop surge, Nicholson was “all business,” recalls Nate Flagg, who served in his unit. Nothing was known about the lieutenant’s politics. The tour was winding down when Nicholson offered a copy of his résumé to one of his Marines who was anxious about applying for work as a civilian. He spotted the bullet point reading “College Democrats,” and within hours the platoon was howling. “It was the biggest mistake he ever made,” Flagg tells me. “We were pretty ruthless about it.” How did Nicholson respond? “That was a long time ago,” Flagg recalls his superior saying. “Everyone is entitled to change their mind.”

That wasn’t all Nicholson had changed. Gone was the arrogant, swaggering collegiate; people who knew Nicholson in the Marines describe a quiet, buttoned-down officer who was intensely devoted to his men. He and Jessie produced a regular newsletter for families in his platoon, and when he brought the entire unit home safely after more than 100 combat missions in Iraq, he was awarded the Navy Achievement Medal. By his telling, Nicholson had been moving rightward since his stint at the DNC in college, but it was the tour in Iraq when he had “given up on any shred of, ‘I’ll be a different kind of Democrat.’” The anti-war rhetoric from Obama, Hillary Clinton and other Democrats proved to be the turning point. “There’s no other way to put this; I was livid,” Nicholson tells me. “I knew what we were doing there. We were stabilizing that country. We made incredible amounts of progress. And what I was hearing back home was a complete and absolute lie, as politicians were running around calling it a failure.”

When he returned stateside in November 2007, Nicholson says, he and his wife went all-in for John McCain. They put up yard signs and made multiple donations to his campaign totaling $500; Nicholson attended a McCain rally and was photographed sitting behind the Republican candidate. As with so much else in Nicholson’s past, however, there is nothing simple about his official switch to Republicanism. He says he voted for Bush in 2004; yet he registered as a Democrat when he moved to North Carolina in 2005. This caused an even bigger headache: When he went to vote for McCain in the May 2008 presidential primary, state law disallowed same-day registration switching. So he says he voted “no preference” in the Democratic primary. The problem: records from Nicholson’s precinct that day suggest nobody voted “no preference.” This doesn’t mean he’s lying about backing McCain, and Nicholson can be excused for rolling his eyes at questions about “paper ballots in North Carolina 10 years ago.” But it’s another example of biographical vulnerability, even as his version of events is pretty convincing. “I would ask people to use common sense,” Nicholson tells me. “I was a Marine, and I was giving my vote, my money, my support and my time to ... the person who was going to be commanding me in a short period of time in combat.”

Nicholson’s contract with the Marines was set to expire in 2008—until he unexpectedly volunteered for a second deployment with a different service branch. “Kevin and I are talking, we’re both getting out, we both want to go to business school,” Cleary recalls. “So the Army calls. ‘Hey, we’re short of lieutenants in Afghanistan’—you can read into what that means, you’ve got lieutenants there getting lit the fuck up—‘and we need unique route clearance capability. We need combat engineers that know how to lead route-clearing platoons to go to Helmand, the most dangerous province in Afghanistan, with an Army platoon.’” Cleary pauses. “Interservice rivalry is an understatement: totally different culture, totally different way of operating, totally different language. And Kevin’s like, ‘I think I’m gonna extend and go to Afghanistan.’ And I said, ‘Are you out of your fucking mind?’”

I had never heard Nicholson discuss this; he mentions fighting in Afghanistan, but not the circumstances. Cleary, who like Nicholson attended Harvard upon leaving the Marines, feels obligated to emphasize and contextualize the decision his friend made. “He voluntarily extended to take on what I view—as a combat engineer who knew what that mission entailed—the most dangerous fucking mission available to a serviceman,” he says. “Basically, you go hunting for IEDs, and when you find them you blow them up. And it’s [the Taliban’s] most effective ambush tactic, so they really want to kill you.”

Kevin Nicholson’s home office is filled with memorabilia from his time in the armed forces. | Darren Hauck for Politico Magazine

Nicholson, a Marine captain by the time of his second deployment, was awarded the Bronze Star for leading the specialized counter-IED team in Afghanistan. He returned home in 2009 and left the military that summer, having been accepted into the dual MBA/MPA program put on by Dartmouth and Harvard. Nicholson was offered a full-time job by McKinsey after interning with the consulting behemoth in the summer of 2010, but deferred the position until he had finished the graduate program. When he did, in the summer of 2012, Nicholson and his young family moved back home to metropolitan Milwaukee.

By this point, word of Nicholson’s political conversion had spread—thanks in part to Jessie sharing on Facebook her husband’s writings on pension reform—and many of their friends, regardless of political affiliation, assumed Nicholson was putting down roots to run for public office. They were right. Over the next several years, the Nicholsons worked systematically to cultivate relationships with activists, donors, elected officials and other political players in the state. That work paid off: Nicholson caught the attention of Jeff Harris, a major GOP donor, and Brett Healy, an influential conservative with deep relationships in Madison. Harris and Healy, according to numerous Wisconsin Republicans I spoke with, became Nicholson’s unofficial gatekeepers: making key introductions, promoting Nicholson to their allies as a once-in-a-generation political prospect, and grooming him for an eventual campaign. “His conservative bona fides were reinforced by the people who vouched for him,” says Matt Batzel, the Wisconsin-based executive director of the grass-roots-organizing group American Majority. “And when you meet him and talk to him, you have no doubt that he’s a conservative.”

Nearly every Republican I spoke with says their introduction with Nicholson was brokered by either Harris or Healy, neither of whom would comment for this story. This is almost certainly how Nicholson got an audience with Dick and Liz Uihlein, the megadonor couple that gave more than $23 million to conservative candidates and causes in the 2016 cycle. (Nicholson tells me only that a “mutual friend” set up the meeting.) It’s known in GOP circles that Dick and Liz don’t always agree on politicians to support; it raised eyebrows, then, after the initial $3.5 million was pledged to Nicholson’s super PAC, when both joined the candidate’s finance committee. Uihlein is one of the Club for Growth’s biggest donors—which didn’t hurt Nicholson’s dogged pursuit of the group’s endorsement—and is poised to rally other Republican rainmakers to Nicholson’s cause.

If financial might is fueling much of the hype surrounding Nicholson, there are reasons to suspect he won’t live up to it. His name identification in Wisconsin is all but nonexistent. Vukmir has her own deep-pocketed supporters, starting with Diane Hendricks, the richest Republican donor in the state. Eric Hovde, a self-funding businessman who finished a close second in the 2012 primary, is weighing another run. The pivotal endorsements in Wisconsin come not from national groups such as the Club for Growth (whose endorsed candidate in 2012 finished third in the GOP primary), but from conservative talk-radio in the southeast corner of the state, which is Vukmir’s territory. His biographical vulnerabilities aside, Nicholson is raw as a retail campaigner and can come across as programmed and mistake-averse. If he wins the nomination and squares off against Baldwin—who is certainly beatable, having run behind Obama in 2012—Nicholson will have to spend next fall tap-dancing around Trump (about whom he’s been advised not to utter a negative word). He’ll also have to show a better command of the issues: Nicholson is playing to a perceived strength by attacking Baldwin’s poor handling of a Veterans Affairs scandal in Wisconsin, but when I ask him about the VA accountability bill that Trump signed into law this summer, Nicholson admits to not knowing the details.

All of that said, and given his manifest upside as a candidate, I was stunned at the degree to which the most prominent Wisconsin Republicans I spoke with—in particular, close allies of Speaker Paul Ryan, Governor Scott Walker and former White House chief of staff Reince Priebus—were dismissive of Nicholson’s chances. Some of this skepticism, in both Madison and Washington, speaks to the pack mentality of veteran politicians trusting only one of their own. There’s also an element of jealousy: Out-of-nowhere phenoms like Nicholson aren’t often well received by members of the party who have spent years paying their dues. But above all, the rookie candidate must overcome a fundamental deficit of trust: In countless conversations, people who have met with Nicholson tell me they aren’t convinced he is truly a conservative.

“I’m not buying it,” Scott Fitzgerald, the state Senate majority leader, tells me. Fitzgerald, who has announced his support of Vukmir, says Nicholson reached out to him earlier this year after Rep. Sean Duffy, a presumed challenger to Baldwin, opted not to run. They had a cup of coffee, and Fitzgerald saw the upside others are investing in. But it wasn’t enough. “I’ve met those types of candidates—sometimes they’re successful, but other times they turn out to be show horses instead of workhorses,” Fitzgerald says. “It’s a roll of the dice with Kevin, because you just don’t know enough about him. You don’t know who he really is.”