He has represented the husband of one of the Real Housewives of Beverly Hills, the licensing company behind the pizza rat viral video and a slew of clients that run afoul of liberal sensibilities — from drug makers and arms dealers to Walmart.
Now Douglas Emhoff could potentially represent the United States as its first Second Gentleman, as his wife, Senator Kamala Harris, campaigns as the running mate of former Vice President Joseph R. Biden Jr., the Democratic presidential nominee.
While Mr. Emhoff’s fund-raising prowess and connections in the legal community in both Washington and Los Angeles were seen as strengths when his wife was challenging Mr. Biden for the presidential nomination, they loomed as a potential liability once Mr. Biden added her to the ticket. Late last month, Mr. Emhoff announced that he was taking a leave of absence from DLA Piper, one of the world’s largest law firms, where he is a partner.
It remains unclear whether Mr. Emhoff will continue to practice law in any capacity, but keeping a connection to a firm with a thriving Washington lobbying practice and offices in places like Moscow and Riyadh could prove problematic. Critics are already scouring his client rosters at DLA and a previous firm, which have included representations viewed suspiciously by progressive voters whom Democrats are relying on to help defeat President Trump.
Working for clients who are entitled to legal representation is distinct from the type of conflicts of interest that have proliferated in Mr. Trump’s Washington. The administration and its associates have routinely used their positions to promote and steer money to the Trumps’ Washington hotel and other entities they own, drawing condemnation from watchdog groups and the Office of Government Ethics.
Even so, if Mr. Emhoff maintains his DLA partnership or continues practicing law elsewhere, it could complicate efforts by Mr. Biden and Ms. Harris to distinguish themselves from the Trump Administration’s practices.
During his decade as a lawyer at the corporate firm Venable, Mr. Emhoff represented the pharmaceutical giant Merck in lawsuits tied to its drug Fosamax; the arms dealer Dolarian Capital in a case related to its sale of AK-47s for use in Afghanistan; and a nightclub owner accused of sexual harassment and sexual battery, including spraying an employee’s hair and body “with a foreign substance” that he removed with “his mouth, lips and tongue.” The case was settled out of court.
Mr. Emhoff left Venable in 2017 for DLA Piper, where he has less of a track record. Though he is not personally registered to lobby, ethics experts flagged the firm’s lobbying practice — which in addition to defense contractors and telecommunications companies includes countries with checkered human rights records like Afghanistan and Bahrain.
Mr. Emhoff’s continued association with the firm, even if he is on leave, could raise suspicions about any interaction between it and clients seeking favor from the government.
“He should leave the firm entirely,” said Richard W. Painter, who served as chief White House ethics counsel during the George W. Bush administration. “Leave of absence still imputes the financial interests of the firm to him.” He added that clients that pay the firm could be accused “of trying to buy influence.”
The Biden-Harris campaign, in a statement, said Mr. Emhoff “has always observed the highest ethical standards to ensure his personal law practice was kept entirely separate from his wife’s work” and that he is now “completely focused” on the campaign.
Some of Mr. Emhoff’s associates argued that he could — and should — create a framework allowing him to serve as both a vice-presidential spouse and a practicing lawyer.
Alex M. Weingarten, a friend and former colleague, said Mr. Emhoff is “fastidious’’ about adhering to ethical standards, and suggested it could send a “good message” about gender roles if he were able to continue his legal work.
“One of the phenomenal parts of this story is that America is seeing that a spouse can be supportive of their spouse’s career, even if the one that needs to be supportive in this instance is the man,” said Mr. Weingarten. He said they had demonstrated that “you don’t necessarily need to sacrifice one for the other, and that her success is not dependent on him, and vice versa.”
Mr. Emhoff, 55, was raised in New Jersey, moving to Southern California with his family at age 17. After graduating from law school at the University of Southern California, he got married and had two children, while building a legal career in Los Angeles. In 2000, he co-founded a boutique law firm, which built a portfolio of clients ranging from car dealers to entertainment companies.
Mr. Emhoff had connections to the entertainment industry, including through his first wife, Kerstin Emhoff, co-founder of the Los Angeles production company Prettybird. But he wasn’t necessarily enchanted by Hollywood, said Mr. Weingarten, whom Mr. Emhoff tried, unsuccessfully, to recruit to the boutique firm. “It was just a general commercial litigation practice,” Mr. Weingarten said, adding, “I don’t think Doug was out specifically hunting for entertainment clients, any more than, you know, trying to make a living and looking for clients.”
But his friends said he wanted to be a part of something bigger, and he convinced his partners to sell the firm in 2006 to the corporate law giant Venable, which was looking to build a presence on the West Coast. Aaron H. Jacoby, one of Mr. Emhoff’s former partners at the boutique firm, initially opposed the sale, but eventually came around. Mr. Emhoff, he said, “is a persuasive guy. He is the type of guy — I don’t mean this in a bad or nefarious way — but he gets what he wants.”
Mr. Emhoff became a partner at Venable, eventually moving into a management role in which he oversaw the firm’s Los Angeles office and the opening of a new San Francisco office. He also recruited lawyers, and made a second run, this time successful, at Mr. Weingarten, who remains at Venable today.
“He is directly responsible for the success that we have enjoyed in L.A. and the success that we are enjoying in San Francisco,” said Mr. Weingarten.
At Venable, Mr. Emhoff represented Willie Gault, the former Olympic sprinter and N.F.L. star, in a fraud case brought by the Securities and Exchange Commission. He was immersed in a multimillion dollar legal battle involving the Taco Bell Chihuahua.
More recently, while at DLA Piper, he represented Mauricio Umansky, the husband of Kyle Richards, one of the stars of the Real Housewives of Beverly Hills, in a real estate dispute with the vice president of Equatorial Guinea.
In 2009, Mr. Emhoff’s first wife filed for divorce.
Mr. Emhoff met Ms. Harris on a blind date in 2013, when she was California’s attorney general, and they were married in a quiet civil ceremony the following year. They now share three residences: a four-bedroom stucco home valued at $5 million in the Brentwood section of Los Angeles and apartments in San Francisco and Washington.
Mr. Emhoff quickly demonstrated a willingness to tailor his finances to suit his wife’s career, divesting individual stock holdings that could be targeted by critics and transferring the money into mutual funds and other instruments that limit potential conflicts.
While friends say Mr. Emhoff has never been particularly interested in politics, he threw himself into his wife’s career. Within hours of Ms. Harris’s speech at the Democratic National Convention, he appeared at a virtual meeting of the party’s L.G.B.T.Q. caucus. Six days later, he joined Ms. Harris at a virtual fund-raiser with Jewish donors, where Representative Ted Deutch of Florida introduced him as the “next Jewish mensch.” On Thursday he will appear with Ms. Harris in Florida.
As a political spouse, Mr. Emhoff has not been afraid to speak his mind. Of Mr. Trump, he recently tweeted that “barely being able to read lies, distortions, and platitudes from a teleprompter IS NOT PRESIDENTIAL.” And after Attorney General William P. Barr downplayed at a news conference last year Robert S. Mueller’s report on the investigation into Russian interference in the 2016 election, Mr. Emhoff drew on his own professional standing: “As a lawyer, and fellow member of the D.C. Bar, I’m just seething right now at Barr’s performance this morning,” he tweeted. “It’s a flat out embarrassment and stain on our profession.”
Ms. Harris has also leaned on her husband’s network to help raise money for her campaigns.
When she ran for Senate in 2016, the largest pool of campaign funds came from Venable’s lawyers and employees. And when she challenged Mr. Biden for the presidential nomination last year, Mr. Emhoff was a liaison with fund-raisers in the legal community. “I’ve been meeting with my fellow lawyers all over the country” he tweeted last November of his efforts on behalf of his wife’s campaign.
But the prominence of Venable as a supporter was not without controversy. As California attorney general, Ms. Harris decided not to pursue an investigation of Herbalife, a nutritional supplements company accused of fraudulent practices, even though her San Diego regional office had sought an investigation in 2015, Yahoo later reported. Herbalife was represented by Venable, though not by Mr. Emhoff personally. Ms. Harris also received $5,400 in donations at the time from an outside lobbyist who did work for Herbalife. By 2016, Herbalife had agreed to pay $200 million as part of a settlement with the Federal Trade Commission.
Julie Contreras, an activist and pastor who has campaigned against Herbalife, said she was disappointed when she learned that Mr. Emhoff’s firm represented the company. “You can’t tell me that as the A.G. of California, you have all these complaints, and then your husband is going to be working for this company?’’ she said. “Somehow that was ethically inappropriate.”
Brendan J. McCormick, a spokesman for Venable, said that “as a matter of practice, neither Doug Emhoff nor the firm represented companies on matters involving” his wife. He also said that the firm’s representation of Herbalife was unrelated to cases brought by the F.T.C. and other state attorneys general.
In 2017, Mr. Emhoff switched firms, becoming a partner at DLA Piper, and became licensed to practice in Washington. He retained a partnership stake in Venable that was worth nearly $1.2 million and it paid him $200,000 in 2018, according to the couple’s tax filings for that year, the most recent one for which they have released their filings.
He was paid $1.34 million by DLA Piper in 2018, tax filings show.
Among the firm’s lobbying clients with interests before the federal government are the telecom giant Comcast, the defense contractor L3 Harris Technologies and the governments of Afghanistan and Bahrain, as well as the Qatari government-funded Al Jazeera Network and the Palestine Monetary Authority. Other clients also have significant stakes in federal government decision-making.
In the past, Mr. Emhoff has taken comfort in his practice, calling it something of a balm.
“With all this other stuff that’s happening in my life right now, it’s great to have,” he told The Hollywood Reporter last year. “It’s something that I love and I’m good at.”
Sarah Lyall contributed reporting and Sheelagh McNeill contributed reporting.