After losing three statewide elections — Tuesday’s loss, the 2017 gubernatorial primary election to Ed Gillespie and a 2013 loss to conservative minister E.W. Jackson for the Republican nomination for lieutenant governor — Stewart may be out of running room for high-profile offices in Virginia.
His future also remains uncertain as chair of the Board of Supervisors in Prince William County — where voters chose Kaine on Tuesday by 29 points.
Returning to the Board of Supervisors may be a stale consolation prize for a political showman who sought to ride the Trump era to heights far beyond the mundane concerns of local zoning cases, school funding and traffic.
If Stewart does seek a fifth term as chair next year, he would face a strong Republican nomination challenge from Martin E. Nohe — the board’s vice chair — in an increasingly moderate county that may be tired of his fights to preserve Confederate monuments in Virginia, his attacks on undocumented immigrants and his past associations with white nationalists that weighed down Stewart’s Senate bid, political analysts say.
In other words, the road to political recovery, if it exists, could be rocky after an election where Virginia’s fractured Republican Party also saw disappointing losses in three House races.
“At this point, I don’t know what that path would be,” said Quentin Kidd, director of the Wason Center for Public Policy at Christopher Newport University in Newport News.
“It’s hard to go back to voters in Prince William County and say: ‘I want to be on the Board of Supervisors’ when all you’ve spent your time doing for the past several years is running for other offices, and embarrassing a lot of residents in Prince William County along the way,” Kidd said.
Stewart said Tuesday night that he plans to take some time to rest and reflect on what lies ahead.
He has been campaigning for office for four consecutive years, Stewart said, referring to his 2015 reelection as county board chair, the brief stint in 2016 as chair of President Trump’s campaign in Virginia, followed by the failed bids for governor and senator.
What’s more, his political rhetoric has apparently hurt his international trade law practice.
Earlier this year, a major automobile industry client dropped Stewart as its attorney, slicing his income in half, Stewart said.
“I have not decided what I’m going to do,” Stewart said. “I am campaigned out right now, I’ll tell you that much.”
Stewart’s often acidic Senate campaign was both a product of deep divisions within Virginia’s Republican Party and a cause of more internal party strife.
His victory in June over state Del. Nicholas J. “Nick” Freitas (R-Culpeper) for the party’s Senate nomination was fueled by arguments that the person to take out Kaine — Virginia’s former governor and Hillary Clinton’s 2016 running mate — should be a take-no-prisoners conservative who models himself after Trump.
Stewart regularly derided state party leaders, most notably when he called General Assembly members who supported Medicaid expansion “flaccid,” “garbage” and “toilet paper” Republicans as he waved a roll in the air outside the state Capitol.
While the tactic helped him win in a low-turnout GOP primary, it undercut his general-election campaign from the start, with several prominent fundraisers and party leaders immediately distancing themselves from Stewart.
“Attacking your own party and the so-called ‘establishment’ is counterproductive,” said John Whitbeck, who resigned as state party chairman shortly after Stewart’s primary election victory. “It leads to people unwilling to donate or volunteer or be generally supportive of a candidacy.”
Stewart’s campaign suffered further from controversies over his ties to well-known white nationalists such as Paul Nehlen, a self-professed “pro-white” congressional candidate in Wisconsin, and Jason Kessler, an organizer of the “Unite the Right” rally in Charlottesville last year that led to the death of Heather Heyer, 32.
Badly trailing Kaine in polls and campaign cash, Stewart briefly tried to soften his abrasive style in hopes of winning over moderate voters, but that effort didn’t last long.
He doubled down on the vitriol by, among other things, implying without evidence that Kaine had been accused of sexual harassment — an attempt to capitalize on Republican anger over the claims of sexual misconduct against Brett M. Kavanaugh during his Supreme Court nomination battle.
The approach drove away many potential supporters.
“I used to like him,” said Miguel Martinez, 27, a former Prince William County police officer who chose Libertarian candidate Matt Waters over Stewart and Kaine on Tuesday. “He’s just ventured a little too far right for me.”
Overall, the failure underscores a need for Virginia’s Republican Party to “retool” in a state where Trump is deeply unpopular, said Stephen Farnsworth, a professor of political science at the University of Mary Washington in Fredericksburg.
The gains by Democrats this year and in last year’s General Assembly races prove that uber conservatives like Stewart will no longer succeed in a statewide race, Farnsworth said.
“A conversation about Confederate statues will not resonate with a statewide electorate in the same way it did 30 years ago,” Farnsworth said.
Nohe (R-Coles) thinks the same thing about Prince William County.
Over the years, Stewart’s campaigns for higher office have hampered the board’s ability to deal with local concerns, such as traffic congestion or crowded schools, Nohe said.
One example occurred in April, when Stewart introduced a measure that would have tripled the tax rate on computers used by businesses, with the extra income meant to cover a drop in residential property taxes by an average of $32 per year while funneling an extra $9 million to county schools.
Stewart cast the idea as a way to make large computer data centers in the county pay their fair share while helping homeowners and students. He noted that the data centers in the county paid less than in other jurisdictions.
But most of his colleagues on the Republican-controlled board saw it as damaging to all local businesses, while potentially driving away lucrative data center companies and thought Stewart was promoting it as a way to win political support from some voters.
Stewart pulled the plan when he saw he lacked support.
“It didn’t make any sense if your goal was to grow the economy in Prince William County,” Nohe said.
Elena Schlossberg, a community activist in Prince William, said voters in the county have grown tired of such moves.
Stewart began his political career in 2003 as a slow-growth advocate representing the county’s sleepy Occoquan district. Shortly after he won the 2006 special election for the chairman’s seat, Stewart began getting contributions from developers and promoted more construction. He then morphed into the scourge of undocumented immigrants that won him national recognition.
“When everything you do is through a lens of votes and there is not a core fundamental belief system, it’s a house of cards that eventually falls apart,” said Schlossberg.
In an interview before the election, Supervisor Jeanine M. Lawson (R-Brentsville) said Stewart would still probably do well if he ran for his Prince William seat next year because voters may show their satisfaction with county services under his leadership.
Lawson said she ran into Stewart at a party in late October in Gainesville to celebrate the county’s success in blocking Dominion Energy from installing power lines near a group of homes.
Stewart was instrumental in getting state authorities to order Dominion to partially bury the lines beneath Interstate-66 as a way to accommodate a data center complex nearby.
That evening, his looming loss appeared to darken his mood, and he seemed ambivalent about settling back into county politics, Lawson said.
But in light of Stewart’s 29-point loss to Kaine in Prince William, Lawson said on Wednesday that it now seems “a lot less likely” that he would do well in a re-election bid.
At his election night gathering, Stewart briefly seemed inclined toward leaving the political spotlight, though he said he hopes to help Trump win reelection in 2020.
“I’ve been chairman for 12 years,” Stewart said. “That’s a long, long time.”
Surrounded by TV news cameras, he then remarked: “I wish you’d given me this much attention sooner!”