Justin Fairfax, the Democratic candidate for Virginia lieutenant governor, at his Arlington campaign headquarters. (Sarah L. Voisin/The Washington Post)

When Justin Fairfax, then a young prosecutor, first entered the chummy world of Virginia politics five years ago to run for attorney general, Democratic insiders greeted him with a resounding “Who?”

The neophyte shocked the Democratic establishment by nearly beating then-state Sen. Mark R. Herring in the 2013 primary.

Since then, he’s methodically done the work necessary to raise his profile and pay dues: He’s served as a campaign surrogate, cultivated relationships with party activists, and helped local candidates canvass and raise money.

Now the 38-year-old lawyer is running again, this time for lieutenant governor. He is hoping his personal story as a young African American striver will help catapult him to office in a purple state that is becoming increasingly diverse but has elected only white men to statewide office for the past ­quarter-century.

Fairfax, who lives in Annandale with his wife and two young children, faces state Sen. Jill Holtzman Vogel (R-Fauquier), an attorney he has criticized for her work helping conservative groups exercise their right to make political donations without disclosing donors.

Virginia candidates for lieutenant governor: state Sen. Jill Vogel (R-Fauquier) and Democrat Justin Fairfax. (Bill O'Leary/The Washington Post and Linda Davidson/The Washington Post)

But Fairfax has also represented controversial clients. They include a student loan company accused of improperly claiming taxpayer subsidies, a food vendor that paid millions to settle allegations of overcharging D.C. taxpayers and the owner of a fraudulent Virginia charity at the heart of a corruption case against a former Democratic congresswoman.

Fairfax declined to discuss his legal practice in detail, citing client confidentiality. On the stump, he prefers to focus on his two years as a federal prosecutor. He plans to keep his day job at the white-collar firm Venable LLP if elected to the part-time office.

Historically, the lieutenant governor’s office has been a steppingstone to higher office. But if Fairfax is aiming higher, he’s not saying.

“What we are focused on is bringing more economic security and prosperity to all Virginians. We want to get people into 175,000 open middle-skill jobs, lower student-interest rates and expand Medicaid,” Fairfax said. “If we focus on those objectives rather than what political offices you may run for in the future, that’s when we really make progress and earn the trust of the electorate.”

An abrupt political debut

Fairfax was raised in his grandparents’ home in a predominantly black neighborhood in Northeast Washington — where his pharmacist mother moved Fairfax and his three older siblings after her divorce. Fairfax says he has a good relationship with his father, a Harvard-educated consultant to nonprofit organizations.

Fairfax attended Catholic school and Duke University on a scholarship, from which he graduated in 2000. He worked as a staffer for the Senate Judiciary Committee for two years before Columbia Law School.

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A year-long clerkship for U.S. District Judge Gerald Bruce Lee of the Eastern District of Virginia — an African American known for his work to diversify the federal bench — brought Fairfax to the Old Dominion in 2005. He worked in the D.C. office of the white-collar firm WilmerHale before returning to the Eastern District in 2010 as a federal prosecutor.

In that role, Fairfax handled low-profile cases involving narcotics and other crimes, and he served on a human-trafficking task force.

He quit after just two years to run for attorney general, with encouragement from Larry Roberts, a top aide to Gov. Tim Kaine (D) when he was executive.

“He felt like people along the way were able to give him a hand up, and his feeling was when you have those opportunities and you see that there are many people who don’t have them, you take the opportunity to pay it forward,” said Roberts, now Fairfax’s campaign chairman and Venable colleague. “And it looked like [Democratic Gov. Terry] McAuliffe was going to be the nominee and McAuliffe was going to have substantial resources to bring, and it was going to potentially be a good year for Democrats.”

Still, Fairfax’s political debut was abrupt.

“He kind of came out of nowhere,” said Lowell Feld, a consultant to Herring’s 2013 bid who runs the Blue Virginia blog.

Fairfax secured the endorsement of The Washington Post, which strategists believe gave him a boost in vote-rich Northern Virginia. His friendly demeanor, his strong public speaking skills and a low-turnout primary were also factors that helped him come within three points of Herring, Democrats said.

Fairfax rebounded from his loss and went from party crasher to insider.

“To Justin’s credit, he didn’t walk away,” said Alexandria Democratic Committee Chair Clarence Tong. “He won the hearts and minds of the rank-and-file Democrats and party activists and party chairs and got a considerable number of endorsements, too. He worked for every single one of them.”

Fairfax has also been embraced by the party’s progressive wing. Vogel and other Republicans have blasted his responses to a questionnaire from a local chapter of U.S. Sen. Bernie Sanders’s (I-Vt.) political group in which he indicated support for a “Medicare-for-all” health-care system and a guaranteed minimum income.

In an interview, Fairfax backtracked, saying he preferred more incremental steps such as expanding Medicaid to low-income adults and a $15 minimum wage.

Susan Swecker, chairwoman of the Democratic Party of Virginia, said Fairfax embodies the next generation of Virginia leaders. “Our state has changed,” she said. “We are a much more diverse state. . . . It’s about time we elect another African American statewide. And he’s well qualified.”

Grappling with race

Virginia hasn’t elected an African American to statewide office since 1989, when L. Douglas Wilder became the first black governor to be elected in any state.

Fairfax idolizes Wilder, and they speak regularly. And he has taken note of how Wilder underplayed the historic nature of his gubernatorial run in the former capital of the Confederacy and forged a winning coalition of white moderates and African Americans.

“People are far more interested in our ideas than they are in our identity. They want public servants who are talking about them and not about themselves,” Fairfax said. “Doug would be first to tell you it’s about the ideas and message you bring and your experience.”

A spokeswoman for Wilder did not respond to an interview request.

While Fairfax speaks forcefully about racial disparities in wealth and criminal justice enforcement, he has proceeded carefully on more explosive issues involving race.

When a primary opponent sought to outmaneuver him by calling for the removal of the state’s Confederate monuments, Fairfax wrote a lengthy statement about dismantling barriers that black Virginians face, saying “symbolism matters, but substance matters even more.”

In the wake of deadly violence during the summer in Charlottesville involving white supremacists angry over plans to remove a statue of Robert E. Lee, McAuliffe, Herring and Democratic gubernatorial candidate Ralph Northam, who is lieutenant governor, called for the removal of Confederate statues from public spaces.

But Fairfax did not go as far. He said that while he personally opposed the statues, the decision should be made at the local level.

Since then, McAuliffe and other Democrats have softened their stance on Confederate monuments in a state where polls show that a majority of voters want them to remain.

During a lively debate, Vogel questioned Fairfax’s grasp of various issues, wondering whether he could “talk intelligently” about policy — a charge Democrats blasted as racially biased.

“To question his ability to talk intelligently is more reminiscent of something from 1957 than 2017,” said Swecker of the state Democratic Party.

Vogel later said in the debate that she had no doubt Fairfax was very intelligent — just misinformed.

Fairfax has repeatedly criticized Vogel’s comments on social media and in speeches to voters, but, through a spokeswoman, he declined to say whether it was racially offensive. In an earlier interview, he said he learned from Wilder to avoid wading into such battles.

“He was serious and substantive even as people attacked him and used dog whistles against him,” Fairfax said of Wilder. “He showed grace and dignity in the face of all that.”

Possible conflicts ahead

Democrats have pummeled the Republican gubernatorial candidate, Ed Gillespie, because his lobbying firm represented a student loan provider in the mid-2000s that was accused of defrauding taxpayers. But at his first legal job, Fairfax represented a different lender involved in the same scandal.

The whistleblower case, filed by a former federal employee, alleged that providers improperly claimed hundreds of millions of dollars in excessive payments from the federal government.

Fairfax, then an associate at WilmerHale, represented Education Loans Inc.; it settled in 2010.

Between statewide runs, Fairfax spent a year as general counsel and vice president of business development at food vendor Thompson Hospitality, which drew controversy for its joint venture with Chartwells to provide meals for D.C. Public Schools.

Shortly before Fairfax joined the firm in October 2013, a former D.C. schools official filed a whistleblower suit alleging that the companies overcharged the city and mismanaged the meals program. Chartwells and Thompson agreed to pay $19 million to settle the lawsuit two years later, after Fairfax left the company.

Citing attorney-client privilege, neither Fairfax nor a representative for Thompson would answer questions about the contract dispute and subsequent lawsuit.

In 2015, Roberts, a partner at Venable LLP, helped recruit Fairfax to his firm’s Tysons Corner office.

The firm is closely intertwined with Democratic politics. Former Venable chairman James Shea is running for governor in Maryland, former partner John Sarbanes was elected to Congress in 2006 and former managing partner Karl A. Racine became the District’s first elected attorney general.

Among Fairfax’s clients is Carla Wiley, a Loudoun County woman who pleaded guilty to charges related to a fraud conspiracy involving former U.S. representative Corrine Brown, a Florida Democrat who served from 1993 to 2017.

In the plea agreement and later testimony, Wiley admitted to working with Brown and her chief of staff to raise money for a charity under the guise of providing scholarships to underprivileged children, but actually spending money on themselves and on lavish events for the congresswoman.

Fairfax and Wiley crossed paths before the case: He was the keynote speaker at an NAACP Loudoun awards banquet in 2015 where Wiley was listed as one of the organizers.

Fairfax confirmed that he is still involved in the case as Wiley awaits sentencing.

In a Venable news release announcing his hiring, Fairfax praised the firm’s work to help banks navigate tougher regulations adopted after the global financial crisis and the firm’s new division focused on state attorneys general.

Fairfax would not say whether he has done any work with the Virginia attorney general’s office.

If he wins in November, Fairfax says, he’ll leave it up to his firm to decide which clients may conflict with his government role.

“My legal work that is part of public record is certainly open for people to look at, and I’m very proud of my legal work and legal record,” Fairfax said.