Glenn Youngkin, the Republican gubernatorial candidate in Virginia, likes to define himself as a “political outsider,” a phrase his campaign often repeats as it seeks to distinguish him from his Democratic rival, former governor Terry McAuliffe.

Yet while he has never held public office, Youngkin is hardly a political novice, having given, along with his wife, Suzanne, more than $1 million in campaign contributions to conservative candidates and political action committees since 1999, campaign finance records show.

Youngkin, a wealthy former business executive, and his wife have been prolific donors to mainstream GOP candidates, contributing hundreds of thousands of dollars to the campaigns of Sen. Mitt Romney (Utah) when he ran for president in 2012 and former House speaker Paul D. Ryan (Wis.) from the 2000s to 2017. The Youngkins also have given large sums to the Republican National Committee, the National Republican Congressional Committee and conservative political action committees, records show.

More recently, as Youngkin ramped up his campaign for governor, he and his wife have contributed to staunch allies of former president Donald Trump, including more than $80,000 to a PAC for two Georgia Republicans who lost high-profile Senate runoff races in January.

Earlier this year, Youngkin used $1 million of his own money to establish Virginia Wins, a PAC that is helping a roster of current down-ballot candidates, including some who have cast doubt on the 2020 presidential election results.

The one Trump proponent to whom the Youngkins have not given money is Trump himself, a fact that has not discouraged the former president from repeatedly endorsing Youngkin, whom he described during a recent GOP rally as a “great gentleman.”

McAuliffe, whose own political rise began as a fundraiser for the Democratic Party, has cited Youngkin’s contributions to portray the Republican as “bankrolling” candidates who are anti­abortion and anti-vaccine. Democrats also have faulted Youngkin for contributions to the Republican Party of Virginia, which recently funded mass mailings to voters that Democrats have called antisemitic and racist.

Youngkin “is willing to do anything, support anyone and back all types of extremists in order to bring Donald Trump’s agenda to Virginia,” Manuel Bonder, a state Democratic Party spokesman, said in an email.

Christian Martinez, a Youngkin spokesman, did not respond to specific questions about the candidate’s contributions. Instead, he said in an email that McAuliffe and the Democrats “are trying to distract from their disastrous record and divisive rhetoric because they’re down in the polls.”

“Glenn Youngkin has been running a campaign to bring people together,” he said.

A political cipher

As a first-time candidate, Youngkin is something of political cipher, with no legislative or governing record to reflect his ideological beliefs. Since May, when he won the GOP nomination, his campaign’s news releases have invariably introduced him with two words: “Political outsider.”

As Youngkin’s campaign has unfolded, voters have learned of the wealth he amassed as a Carlyle Group executive — estimates range as high as $400 million — and that he has invested $16.5 million in his own campaign.

Less well-known is the Youngkins’ history of contributions to Republican campaigns — more than 250 donations since 1999 — suggesting that the couple have been far from casual observers of GOP politics at the national level and, more recently, in Virginia.

The donations also show the evolution of the Youngkins’ political tastes, from reliable supporters of establishment Republicans to benefactors of candidates staking out positions more aligned with Trump.

In 2004, for example, they gave $4,000 to the reelection campaign of President George W. Bush, the scion of an elite Republican political family. Seventeen years later, Youngkin’s PAC gave $3,000 to Virginia Del. Ronnie R. Campbell (R-Rockbridge), who had been among three Republicans who signed a letter to Vice President Mike Pence raising questions about the integrity of the 2020 election and asking him to discard the commonwealth’s results.

Rep. Glenn Grothman (R-Wis.) received $5,400 from the Youngkins in 2018 after he had drawn attention for divisive statements, including that affirmative action was “offensive,” that “almost no black people today care about Kwanzaa, and that public employees should be required to work on Martin Luther King Jr.’s birthday, even though it’s a federal holiday.

“It’s very clear from the donations, this is a person who has been heavily involved in Republican politics,” Bob Holsworth, a longtime Virginia political analyst, said of Youngkin. “And it shows that recently he has been very strategic in his donations to ensure that he isn’t seen simply as a Romney-Ryan kind of Republican. Not only has he given a lot but he did so with an eye to this campaign.”

John Fredericks, a Virginia-based conservative radio host who is supporting Youngkin, said he regards the Republican as more of a political outsider than Trump, who had flirted with candidacies and supported various conservative causes before running for president in 2016.

“Before Youngkin started running for governor, I had never heard of the guy,” Fredericks said. “It’s not like he came up through the Republican committees, ran for council and then Congress. I don’t know how a candidate could be any more of an outsider.”

As for Youngkin’s history of campaign contributions, Fredericks said the donations were more relevant to the “inside baseball crowd that goes to the caviar receptions. The average person doesn’t know about that. They don’t pore through campaign contributions.”

McAuliffe could not easily cast himself as a political outsider when he first ran for governor in 2009, given his background as a fundraiser, chairman of the Democratic National Committee and confidant of former president Bill Clinton and former secretary of state Hillary Clinton.

At the same time, McAuliffe had to fend off rivals’ barbs that he was a “carpetbagger,” a Syracuse, N.Y., native who had moved to Virginia and was using the commonwealth to launch his political career.

Nevertheless, like Youngkin, McAuliffe emphasized his business experience and told a reporter that year that he was a good choice for voters “looking for someone new, someone who hasn’t been part of the partisan bickering in Richmond, a business guy to come in and shake things up.”

Flexing financial muscle

Between them, the Youngkins’ contributions add up to about $1.5 million, according to Federal Election Commission records. They gave a preponderance of their contributions — more than $1 million — in the past decade, sometimes displaying their financial muscle on the same day.

On June 22, 2012, for example, each gave $50,000 to a Romney campaign fund.

A majority of the couple’s donations are in Glenn Youngkin’s name. But Suzanne Youngkin, who often lists herself as a “homemaker,” made nearly 80 donations on her own, totaling more than $400,000.

Most recently, Suzanne Youngkin has made $2,500 contributions to Republican women campaigning for House seats, including several — Nicole Malliotakis in New York, Rep. Maria Elvira Salazar (Fla.), and Rep. Beth Van Duyne (Tex.) — who have been endorsed by Trump. At least two women to whom Suzanne Youngkin gave money — Van Duyne and Rep. Stephanie I. Bice (Okla.) — voted on Jan. 6 to reject election results in Pennsylvania. Bice also voted to oppose results in Arizona.

In his early years as a contributor, Glenn Youngkin was a more modest donor. For example, he gave $2,000 to former Virginia governor George Allen (R) when Allen ran for the Senate in 2000. In 2010, Youngkin contributed $2,400 to Sen. Robert F. Bennett (Utah), who was ousted that year by the tea party movement.

The breadth and heft of the Youngkins’ donations picked up in 2012 when they contributed just over $200,000 to entities affiliated with Romney’s presidential campaign.

Ryan, on his own, has also benefited from the Youngkins’ largesse. Over the course of two decades, the Youngkins gave various Ryan campaign funds nearly $160,000, spread out over more than two dozen donations.

When asked about their relationship, a Ryan spokesman, Kevin Seifert, said only that they have been friends “for a long time.” A vacation-style photo from 2017 on the Instagram account of Grant Youngkin, the candidate’s then college-aged son, shows a smiling Ryan in a T-shirt and swimming trunks, posing between the younger and elder Youngkins.

Other mainstream Republicans to whom the Youngkins have contributed include former Virginia congresswoman Barbara Comstock, whose campaign received $40,000; Sen. John McCain’s 2008 presidential campaign, which received $4,800; and former Florida governor Jeb Bush’s 2016 presidential campaign, which received $18,000.

In the past five years, records show that the Youngkins started donating to the party’s most outspoken members, including Sens. Lindsey O. Graham (S.C.) and Rand Paul (Ky.). In 2018, the Youngkins contributed $20,000 to the reelection campaign of Sen. Ted Cruz (Tex.).

In recent months, Cruz has stumped for Youngkin in Virginia, telling crowds that they have been friends “for years.”

“We have stayed with Glenn and Suzanne,” Cruz told one audience, referring to himself and his wife, Heidi. “We have floated in the river with them on inner tubes. There may or may not have been some beverages involved.”

Youngkin’s PAC has given money to an array of conservative candidates seeking House of Delegate seats, all 100 of which are up for election Nov. 2. The beneficiaries include several candidates — Harold Pyon, Karen Greenhalgh and Tara Durant — for whom the Republican Party of Virginia distributed mass mailings that Democrats have assailed as bigoted.

Pyon, who has received $33,500 from Virginia Wins, including $20,500 in September, has denied that antisemitism was the intent of the mailer, which depicted his Jewish opponent, Del. Dan Helmer (D-Fairfax), with his nose appearing to have been digitally altered to seem larger as he gazes at stacks of gold coins.

Greenhalgh, who has received $33,500 from Youngkin’s PAC, has tweeted she did not authorize a mailing the state GOP sent attacking her opponent, Del. Alex Askew (D-Virginia Beach), who is Black, though it was not clear if she was referring to one that depicted him suspended in the air from ropes or another in which his face is framed by flickering flames.

Durant, who has received $33,500 from Virginia Wins, has not commented.

Youngkin’s long list of contributions include a rare $2,800 donation he made to a Democrat — Michelle Caruso-Cabrera, a former Republican who switched parties before challenging Rep. Alexandria Ocasio-Cortez (D-N.Y.) in the 2020 primary.

Ocasio-Cortez defeated Caruso-Cabrera by 35,000 votes.