“He wanted to please,” his mother says.
Over the next four decades, as he became his family’s first college graduate and a Republican and migrated to Virginia, Stewart never outgrew his White House dream, an ambition that drives his campaign to unseat incumbent Sen. Tim Kaine (D).
Yet just about everything else about Stewart has changed, including, most notably, his transformation into the enfant terrible of Virginia politics.
Instead of Kennedy, Stewart’s North Star is President Trump, whose caustic, insult-laden antics Stewart apes with unapologetic gusto. Stewart’s turn astonishes those who have known him the longest, including members of his family who still live in this blue-collar city etched into the bluffs overlooking Lake Superior.
“I’d give you a kidney, but I’d never vote for you,” Stewart’s cousin, Frank Grandson, 63, told him recently.
Grandson, a Democrat who supervises production for a Duluth publisher, is accustomed to roiling family debates about politics around a fire at the Stewarts’ cabin outside the city. Once mostly Democratic, the clan now includes Republicans, and like many families, their debates have grown more fierce during the Trump era, particularly as the hour gets late and alcohol is poured. Although they disagree on most issues, Grandson said he long considered Stewart a “moderate” in his views and temperament.
But after Stewart embraced Trump two years ago, Grandson asked, “What in the hell are you thinking?” And when Stewart appeared in a video surrounded by Confederate battle flags, Grandson sent him a text: “WTF?”
Stewart’s wife was also startled by images of her husband and the flag and told him he had committed a political blunder.
“He said there’s nothing wrong with it,” said Maria Stewart, who, despite her upbringing in Sweden, quickly understood the racial undertones of the flag. “He doesn’t get it sometimes.”
Earl “Rocky” Stewart Jr., 63, an electrician in Duluth and a Democrat, blanches at his brother’s histrionics. “It’s not the Corey I know at all,” he said, “but I suppose it’s just that switch you have to turn on when you’re in politics.”
Out of loyalty, Rocky Stewart has contributed $500 to his brother’s campaigns, even as he disagrees with his positions and choice of words, such as a statement he made about undocumented immigrants, saying Prince William County would “hunt them down.”
“Cringeworthy,” Rocky Stewart said.
“I know he’s a decent, honest person, but I can’t explain this,” Grandson said of Stewart’s transformation. “It’s like finding out your uncle likes to wear a dress and high heels on the weekend.”
The true nature of Stewart’s political core has been a riddle since his election as chairman of the Prince William Board of County Supervisors 12 years ago. He has toggled between mundane local governance — controlling development and spending, for example — and polarizing concerns such as deporting undocumented immigrants, railing against establishment Republicans and protecting a statue of Gen. Robert E. Lee in Charlottesville.
It was his defense of Confederate monuments during his failed 2017 gubernatorial campaign that linked him to white supremacists — ties that he has since struggled to disown.
“You might ask, ‘Who is the authentic Corey Stewart?’ ” said Martin E. Nohe, a Republican supervisor in Prince William who has known Stewart for two decades. “The answer is that he is someone who changes when it benefits him to do so.”
In Kaine, Stewart is facing his most daunting hurdle, an incumbent with a 20-point lead in the polls and a mountain of cash in a purple state where Trump is largely unpopular. But Stewart insists that the president is stronger in Virginia than polls suggest and that he will defeat Kaine by appealing to the president’s blue- and white-collar coalition and by running a “vicious, ruthless” campaign.
“I’m never going to espouse anything I don’t believe in,” said Stewart, 50. “But short of that — if it’s not unethical or illegal — I’ll do it.”
'As fast as I can'
On Christmas Day in 1985, Corey, then 17 and in a suit and tie, grinned as a cousin focused a video camera on him. “Well, Corey,” the cousin said, “when you’re president, this film is going to be worth a lot of money.”
His family was well aware of his lofty ambition, one that exceeded anything his father, a longshoreman, had envisioned for himself. A heavy smoker who liked to splash vodka in his coffee, Earl Stewart was the family’s disciplinarian. When his children misbehaved at dinner, he’d jab them with his fork or make them stand in the corner for an hour, hands over their heads.
After one of Corey’s brothers tried to hide a failing report card, Earl Stewart beat him with a belt, a moment that terrified Corey and made him determined to “get straight A’s for the rest of my life.” “As kids, we liked it when he was working and wasn’t home,” Rocky Stewart said of their father. “We were raised to be seen and not heard.”
Once the nation’s busiest port, Duluth offered ample opportunity for longshoremen loading ships with iron ore and grain. A union man and loyal Democrat, Earl Stewart made a comfortable living until ports in other parts of the country lured away business.
Earl Stewart was angry as his wages declined by two-thirds. Three of his sons had followed him into blue-collar work. But fourth-born Corey was on a different path. He liked to read about Kennedy, quote Winston Churchill and recite the presidents’ names in order.
At his father’s urging, Stewart joined the debate team at Duluth Central High School but initially struggled with speaking extemporaneously, unable to fill more than a minute. “I thought, ‘This kid isn’t going to make it,’ ” said Jack Armstrong, the coach.
By graduation, Stewart evolved into a “competent” debater, his coach said. His allegiance was already drifting to the Republicans, in part because he was captivated by then-President Ronald Reagan and also because of the GOP’s opposition to abortion, a position held by his mother, a devout Catholic. Stewart’s embrace of the Republicans irked his father. His grandmother refused to speak to him for several months.
Stewart attended Georgetown University because he wanted to get to Washington, the epicenter of politics. “The gentleman from Minnesota,” his roommate, Tom Manzi, called him, a teasing nod to Stewart’s aspirations. Christie Garcia, a student whom Stewart dated, described him as affable and “boring” — more interested in academics than romance, a preference that “broke my heart.”
Stewart received a law degree from the William Mitchell College of Law in St. Paul, after which he was hired at a Washington firm. By then he had married Maria, with whom he moved in 2001 to Prince William and entered politics.
An old Georgetown roommate — by then a journalist — advised him on how to ensure headlines: Return reporters’ calls; speak in simple sentences; be edgy.
In 2003, Stewart ran for supervisor, his first race. Selling himself as an anti-growth candidate, he assembled a bipartisan coalition and, in the primary, defeated a Republican backed by the district’s reigning power broker, then-Rep. Thomas M. Davis III (R).
Before he completed his first term, the chairman’s seat opened, forcing a special election that Stewart won. At 38, three years after entering politics, he was top man in one of Virginia’s fastest-growing counties.
“Up or out,” Stewart told his staff, his mantra for wanting to advance “as fast as I can.”
'This isn't so bad'
Facing reelection the following year, Stewart found a new issue: illegal immigration. He seized on a colleague’s proposal to slash services to undocumented immigrants and allow police to seek proof of citizenship during routine stops.
Thousands flooded the county to testify at board hearings that drew national attention. Adversaries called him a racist. He received death threats. For the first time, he was besieged by interview requests, virtually all of which he accepted.
Along the way, he lost allies such as Elena Schlossberg-Kunkel, an anti-growth activist who had hosted a fundraiser for him the year before.
“I tried to tell Corey as a friend and fellow human being that he was going down a path that would haunt him as a moral and ethical issue,” she said. “He’d say, ‘I hear what you’re saying.’ But it was like he couldn’t stop himself.”
More than a decade later, Stewart describes the period as “traumatic,” one that he navigated without knowing whether his political career would implode.
“It made me more combative,” he said. “I became a villain in the eyes of a lot of people and I realized —” he paused for a moment — “ ‘This isn’t so bad.’ When you’re vilified on a legitimate issue, you earn a whole lot of die-hard supporters.”
He won reelection with 55 percent of the vote and began publicly flirting with running statewide. But it wasn’t until six years later that he sought the Republican nomination for lieutenant governor, a race he lost to firebrand E.W. Jackson of Chesapeake.
Stewart concluded that he needed to attract voters beyond Northern Virginia. “The question was, ‘How in the hell am I going to get my name out there?’ ” he said.
He found his answer in 2015, attending his first Trump rally in Manassas. “I’d never seen that level of excitement,” he said. “I knew I wanted to be part of it. This was my opportunity to advance to the next level.”
To Stewart, who became for a time the chairman of Trump’s Virginia campaign, the candidate’s crude, anything-goes style meant “you didn’t have to be the perfect politician with the perfect words. You could be whatever the hell you wanted to be.”
Newly emboldened, he entered Virginia’s 2017 gubernatorial race as a Trump clone, tagging his opponent “Establishment Ed” Gillespie and posting messages on Facebook such as “Hey Hillary, you suck!”
He lost the primary by fewer than 5,000 votes, astonishing the Republican establishment. A year later, Stewart won the GOP nomination in the Senate race, a result he interpreted as validation of his Trumpian bluster.
Yet Stewart acknowledges that the controversies of the past two years have cost him. His law practice — earning him $600,000 in 2017 — is down 50 percent because his biggest client dropped him. “I am broke,” he said.
Perhaps nothing was more damaging than his association with white nationalist Jason Kessler, who organized the Unite the Right rally that turned into a deadly riot in Charlottesville in 2017, and Paul Nehlen, an anti-Semitic congressional candidate from Wisconsin.
Stewart insists he was unaware of Nehlen’s extremism when he called him a “personal hero” in early 2017. The same goes for Kessler.
Yet Stewart has other allies with vitriolic views. Rick Shaftan, his campaign consultant, once described the NAACP as “the black KKK, only more violent.” Eugene Delgaudio, a former Loudoun County supervisor who has introduced Stewart at campaign events, has referred to former president Barack Obama as a “child molester” and has accused “homosexuals” of seeking to “brainwash children.”
Stewart said he disagreed with remarks made by both men but described Shaftan as “brilliant” and Delgaudio as a “truly good person.”
Yet he was infuriated when another consultant tweeted under Stewart’s name that a Muslim Democrat then running for governor in Michigan was an “ISIS commie.” He fired the consultant and ordered the tweet deleted.
Another infamous tweet that Stewart claims not to have written — “Nothing is worse than a Yankee telling a Southerner that his monuments don’t matter” — prompted widespread ridicule because of his Minnesota roots.
At first, Stewart was irate over the tweet, the author of which is a former aide he declined to identify. Then he noticed that the post “actually got me a whole lot of attention.”
The tweet stayed.
A new mold
Returning to Duluth in August for a family gathering, Stewart was his usual genial self, joking with his brothers, sister and cousins around the fire, though Grandson noticed that he seemed bothered.
Someone had called him a “neo-Confederate,” Stewart complained, a term he had never heard.
And those constant depictions of him as a racist? He was fed up.
Grandson told his cousin that perhaps it had been a mistake to pose for photos with Confederate battle flags.
“Maybe that wasn’t such a smart move,” Stewart conceded, according to his cousin.
A month later, Stewart sipped tea in his plantation-era manse in Woodbridge, surrounded by Victorian settees and Tiffany lamps. His red pickup truck was parked outside.
Stewart does not like to admit mistakes, but he conceded that his Confederate dance was “politically costly.” Still, he added, his defense of the monuments “probably won some people over, too.”
He dismissed the idea that his political act is just that — an act intended to draw attention, gin up support and power his drive for more of the same. He knows he could “go up in a ball of flames.”
“But if I win,” he added, his voice picking up intensity, “it’s spectacular. It will propel me right to the top. I won’t just be a regular senator. I’ll be the guy who wasn’t supposed to win.”
Whatever the outcome, Stewart has achieved one goal: not being like the politicians he detests, the ones “with the same blue suit, red tie — flag pin in the lapel — and the same freaking haircut.”
“I never wanted to be the guy who is just another guy,” Stewart said.
On that score, at least, few would argue that he is anything but a success.
This is the first in a two-part look at the candidates running for U.S. Senate in Virginia. Tomorrow: Tim Kaine.