Trump, Gov. Youngkin to appear together for the first time in Va. rally

Trump and the governor have run hot and cold on each other since Youngkin entered politics three years ago, with relations particularly strained as Youngkin aggressively flirted with a presidential bid of his own. But now both see an upside to locking arms. The pair met privately for the first time just two weeks ago.

Youngkin opted out of previous chances to meet. When Trump led a rally in Richmond on the eve of the Super Tuesday primaries in March, Youngkin said he had a conflict and showed up instead at the University of Virginia-Duke basketball game in Durham, N.C. Youngkin, citing another conflict, skipped a rally organized on behalf of his own campaign in October 2021, which Trump phoned in to and his former White House adviser Stephen K. Bannon headlined.

Trump has fared poorly at the polls in Virginia, losing by five points in 2016 and twice that in 2020. He dragged the state GOP down with him while in the White House, as Democrats won full control of state government in 2019 for the first time in a generation. Trump did not seriously contest Virginia four years ago; his lone campaign appearance, in Newport News, was intended to reach voters in the swing state next door, North Carolina, a media market that Friday’s rally also will reach.

But that was before Biden’s popularity took a dive and recent polls suggested the Old Dominion’s presidential contest was a dead heat. Earlier this month, the Cook Political Report shifted Virginia from “solid Democratic” to “likely Democratic.” (Although Cook also found that the state still was at “low risk” of flipping to Trump.)

Though independent political analysts and even Republican strategists don’t rate Virginia a top-tier swing state, Trump and Youngkin have declared the commonwealth in play. What’s more, Youngkin allies credit the governor with making Virginia competitive with his “common-sense conservative” policies in education, public safety and cost of living.

“The fact that we’re even talking about it as competitive — two words: Glenn Youngkin,” said Zack Roday, a Republican strategist who has done work for Youngkin in the past. He said the Virginia GOP was in a “pretty dark” place before the governor flipped Virginia in 2021. “We had no bench, we had no wins, we had no hope.”

Youngkin suggested in a recent Fox News interview that his record, as much as Trump’s, has opened the door for Republicans in a state that hasn’t picked one for president since George W. Bush in 2004.

Voters “want Trump back in the White House because he built a strong America. And that’s exactly what we’ve seen in Virginia over the course of the last couple years,” Youngkin told Fox’s Sean Hannity on June 10. “Common-sense conservative policies work. We’ve unleashed a rip-roaring economy in Virginia, and I think they want to see it on a national level.”

The idea that Trump could boost his chances by campaigning in Virginia or sidling up to Youngkin drew derision from the Biden campaign and other Democrats, who note that Biden has opened six campaign offices in the state while Trump’s campaign has no visible ground game.

“Virginians have rejected Trump every time he’s run here, and his MAGA allies were soundly defeated last year after they campaigned on his agenda of banning abortion across the Commonwealth,” Jake Rubenstein, state director for the Biden campaign, said in a written statement. “We’re mobilizing voters in every corner of Virginia and looking forward to beating Trump for a third time in November.”

“Every time Donald Trump opens his mouth on Virginia soil, he’s just widening our margin,” said Richmond Mayor Levar Stoney, one of the state’s two representatives on the Biden-Harris campaign’s national campaign advisory board.

A political novice and private equity chief who poured $20 million of his personal fortune into his gubernatorial campaign, Youngkin flipped seemingly solidly blue Virginia one year into Biden’s term. The win drew national attention, given its off-year timing and the political fame of Youngkin’s Democratic rival, former governor and Clinton pal Terry McAuliffe.

But Youngkin has yet to replicate that electoral magic, despite consistently healthy job-approval ratings. Most of the gubernatorial and congressional candidates he stumped for across the country in 2022 lost. A year later in his own state, Democrats won full control of the General Assembly in contests that Youngkin had called a midterm referendum on his governorship.

Virginia House Speaker Don L. Scott Jr. (D-Portsmouth) questioned how Youngkin could smooth Trump’s path in a state that just rejected the governor’s aggressive push in November’s legislative elections.

“Virginia is a competitive state but … whatever they’re smoking, they need to realize that we have not legalized it in Virginia yet,” he said.

Roday, who led Youngkin’s 2023 legislative effort, acknowledged those losses but noted that the results in key races were close and that Democrats have paper-thin margins in both the House and Senate.

“Sure, we didn’t win,” he said. “Virginia’s been on a razor’s edge and that’s the Youngkin effect. … It’s not whether Youngkin delivers victory, it’s the fact that Virginia’s on the board. That’s what Youngkin has done.”

Roday is among the Republican strategists who stop short of claiming Virginia is fully in play but say it could get there. “A confluence of things have to happen for [Virginia to acquire] North Carolina-type status, where it cracks the top seven or top six [swing states], but it’s competitive,” he said.

Henry Barbour, a Youngkin supporter, GOP national committeeman from Mississippi and nephew of that state’s former governor, sees it that way, too.

“Look at what he’s done in a swing state — cut taxes, fought for parental rights, governed as a conservative — and he’s very popular,” he said. “I think he has a bright future and I’m sure former president Trump appreciates that Governor Youngkin helped put a blue state into a competitive state of play.”

Susan Swecker, chairwoman of the Democratic Party of Virginia, agreed that the rally will be a boost — but for Democrats.

“Virginians see Trump for what he is: a convicted felon who’s on an increasingly unhinged and dangerous quest for power, fuels political violence, and said the extremists who marched on Charlottesville were ‘very fine people,’” she said. “It’s fitting that a loser like Trump would choose to head to a state that’s rejected him twice, where he and his agenda of banning abortion are so toxic that local Republicans have been forced to avoid campaigning with him over the past few years, and that is poised to reject him again in November.”

Whatever its impact on voters, the Trump’s rally with Youngkin will mark a milestone in the sometimes-bumpy relationship between two wealthy business figures who made unlikely U-turns into politics.

Youngkin, a former Carlyle Group executive, embraced Trump and refused to acknowledge that Biden had legitimately won the White House in 2020 as he sought his party’s gubernatorial nomination in 2021.

While Youngkin accepted Trump’s endorsement, he admitted Biden’s legitimacy and kept Trump at arm’s length during the general election, leaning into MAGA culture-war themes about “critical race theory” and “election integrity” with a friendly, basketball-dad persona that played better with suburban moderates.

Trump has griped privately and publicly that Youngkin failed to give him enough credit for his win. That Youngkin spent the first two years of his term exploring a 2024 presidential bid only deepened the rift, prompting Trump to lash out on social media in a way that dovetailed with the GOP’s anti-China rhetoric.

“Young Kin (now that’s an interesting take. Sounds Chinese, doesn’t it?) in Virginia couldn’t have won without me,” Trump wrote.

Youngkin has toggled in and out of MAGA messaging over the years — campaigning in 2022 for election-denying gubernatorial candidates such Kari Lake in Arizona and decrying Trump’s various criminal indictments while staying neutral in the presidential primary until rival Nikki Haley suspended her campaign the morning after Trump’s Super Tuesday rout.

Youngkin tweeted his endorsement that Wednesday about 9 p.m., when it was buried in other news breaking at that very hour: The $2 billion, taxpayer-backed sports stadium the governor had been seeking for the Washington Capitals and Wizards was dead.

Trump and Youngkin seemed to put all that behind them at a private meeting on June 12 at Trump National Golf Club in Northern Virginia, where the governor presented internal polling suggesting his state was winnable. The campaign released a blurry photo of Trump standing beside Youngkin, the former commander in chief flashing a thumbs-up that Youngkin — in a minor breach of Trump photo etiquette — did not reciprocate.

The awkwardness persists.

When after that meeting Trump breezily told a reporter he could consider Youngkin for his running mate, the governor’s team went dark, opting not to respond to requests for comment.

Widely known to be eyeing a run for president in 2028, Youngkin has signaled an interest in being part of the conversation — he has resumed national political travel and is waiting to hear if he snags a prominent speaking slot at the Republican National Convention next month — but not part of the ticket.

In his recent interview with Hannity, Youngkin sidestepped when the Fox host repeatedly asked if he would serve as Trump’s running mate if asked. Youngkin said he had to finish his job as governor — a shift from when the governor was considering a 2024 presidential bid and pointedly refused to commit to completing his term, which wraps up in January 2026.

“I would be honored and humbled and tell him that there’s a ton of talent in the Republican Party today and I’ve seen them everywhere and it’s my job to finish my time as governor and help him win Virginia,” Youngkin told Hannity.

“Is that a hard no?” asked Hannity, breaking into a chuckle as Youngkin reprised his bit about “so much talent.”