Meet the REAL Doug Emhoff: VP Kamala Harris' husband's cheating with the family nanny... work for dodgy arms dealer... and well-timed 'feminist' rebrand as his wife runs for president

It has been awkward timing, to say the least, for the Kamala Harris campaign to begin rolling out merchandise featuring a four decade-old picture of the vice president's husband.

On Friday, coffee mugs emblazoned with an image of a handsome - noticeably younger, thinner and fuller-haired - Second Gentleman Doug Emhoff went on sale on kamalaharris.com.

For just $20.00 – you too could wake up to that smiling face in the morning.

'Kamala's campaign team tells me you liked this photo so much they made merch out of it,' Emhoff, 59, joked to his Gen-Z fanbase on Instagram, who have been charmed by the unassuming, ex-lawyer who seems perfectly content in his wife's shadow.

But less than 24 hours later, Doug's gag wasn't landing as well.

DailyMail.com reported exclusively on Saturday that Emhoff's first marriage to film producer Kerstin Emhoff fell apart after he had an affair with his young daughter's teacher, Najen Naylor.

Emhoff confirmed the illicit romance in a statement to CNN.

Though he did not address some of the grim details of the Mail's reporting – specifically, that his affair with Naylor, who also moonlighted as the family nanny, resulted in a pregnancy and, according to Naylor's close friend, she 'did not keep the child.'

(It's not clear if the pregnancy was terminated or if a child was given up for adoption.)

This would be a shocking revelation about any political spouse but it's even more so for Emhoff, who is now in the running to become America's first First Gentleman.

What's more, since his wife became Vice President in 2020, he has embarked on a public crusade presenting himself as a role model for American men.

'[Toxic masculinity] is something I have thought about a lot, something I've spoken about a lot,' Emhoff told MSNBC host Jonathan Capehart in March 2023. 'There's too much of toxicity – masculine toxicity out there.'

'We've kind of confused what it means to be a man, what it means to be masculine, where you've got this trope out there where you have to be tough, and angry, and lash out to be strong,' he proclaimed. 'It's just the opposite. You know, strength is how you show your love for people.'

It's remarks like those and others Emhoff has made over the years that are not sitting well with critics.

And while many political experts concede that his infidelities likely won't hurt his wife's electoral ambitions, they do expose him to allegations that he's a craven hypocrite.

'I've got to be honest, I don't really give a s*** about Doug Emhoff and his first marriage,' said former Fox News anchor Megyn Kelly on her podcast Monday.

'What I do care about is his preaching and lecturing to the rest of us on what it means to be toxically masculine…' she explained.

'Is it toxic masculinity to eff around on your first wife with your children's nanny and then get her pregnant?' Kelly asked.

Indeed, there's a lot more to Doug Emhoff than a flattering picture on a coffee cup and some lofty ideals. 

And now, as everything from his infidelity to his legal work for a OxyContin pusher and problematic arms dealer comes to the fore, many are asking: Who is the real Doug Emhoff?

He married his first wife, film producer Kerstin Emhoff, in 1992 and they had two children, Cole, 29, and Ella, 25.

As an up-and-coming lawyer in Los Angeles, Emhoff worked at two prominent firms before opening a boutique law operation in 2000, which was sold six years later to corporate giant Venable.

Emhoff became a managing director of the firm's West Coast offices.

One of Emhoff's law partners, Aaron H. Jacoby, told The New York Times in 2020 that he was hesitant to sell to Venable, but Emhoff convinced him.

'[Emhoff] 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,' Jacoby said.

It was also around this time that Emhoff's marriage to Kerstin was ending after she discovered his affair with Najen Naylor, sources told the Mail.

Emhoff's daughter was 10 at the time and his son was son 15.

Naylor left her job as a teacher at The Willows, an elite private elementary school in Culver City, California amid the scandal.

By contrast, Emhoff's career at Venable was only taking off.

He reportedly represented Abbott Laboratories, a multi-national health care company, in an OxyContin fraud case.

Among other cases, Abbott was accused by the state of West Virginia in 2004 of inappropriately marketing highly addictive OxyContin to its citizens, while allegedly downplaying the drug's risks. 

The case was settled in 2004 when Purdue Pharma LP, the Connecticut company that developed OxyContin and has been accused of stoking America's opioid crisis, agreed to pay the state $10 million.

Abbott was working on Purdue's behalf – and a clause in their contract reportedly indemnified the business. Neither company admitted wrongdoing.

In 2011, Emhoff reportedly represented international arms dealer Dolarian Capital in a case against another weapons broker, who was accused of lying about securing an export license to ship thousands of AK-47s from Romania to the Afghan national army.

In 2019, Ara Dolarian, the owner and president of Dolarian Capital, was arrested by the FBI and charged with illegally brokering the sale of millions of dollars of military-grade arms from Eastern Europe to Nigeria without permission from the State Department.

Dolarian pleaded guilty that year and was reportedly jailed in 2023 for 14 months.

Emhoff was also reportedly part of the team defending pharmaceutical giant Merck in 2013 when it was sued over an osteoporosis drug, Fosamax, that 1,200 plaintiffs alleged caused their jaw bones to deteriorate. 

Merck did $3 billion in sales of Fosamax in 2007 alone. The company settled with the claimants in 2013 for $27.7 million.

As Emhoff's legal career progressed, so did Harris' political career. They married in August 2014, while she was California's Attorney General.

Emhoff appeared to use his prominent position in Venable to help his new wife on her way up.

When Harris ran for Senate in 2016, the largest pool of her campaign funds came from Venable's lawyers and employees, according to the New York Times.

Emhoff left Venable and joined DLA Piper as a partner in 2017, splitting his time between the company's LA and Washington DC offices, as Harris started her new job as a senator in the nation's capital.

And when Joe Biden tapped Harris to join him on the 2020 Democratic presidential ticket, Emhoff took a leave of absence from the firm.

'I really decided to lean in on this issue of men supporting women, professionally and personally, so they can succeed, even if that means stepping away from my own career,' he told a group of young girls at a charity event in 2022.

The move was praised as a 'revolutionary' departure from the old-fashioned 'gendered' norm of the man as the breadwinner.

However, Emhoff's decision to put his legal career on hold may not have been entirely down to his feminist sensibilities.

There were grumbles in the media over whether Emhoff's job would prove problematic for Harris politically. 'Will Doug Emhoff's Legal Career Be an Issue for the Biden-Harris Ticket?' asked a New York Times headline in September 2020.

Ethics experts also flagged potential conflicts of interest between DLA Piper's lobbying work on behalf of global media company Comcast, defense contractor Raytheon, the Puerto Rican government and countries like Afghanistan and Bahrain.

By November 2020, after Biden and Harris' electoral victory, Emhoff left DLA Piper.

The closest parallel to Emhoff and his career choices are those of Marilyn Quayle, the wife of President George H.W. Bush's vice president, Dan Quayle.

She abandoned her legal career in 1989 when concerns over conflicts of interest between her clients and her husband's role became untenable.

Perhaps, Emhoff is not such a trailblazer after all.

Today, Doug is teaching entertainment law at Georgetown Law where he is paid nearly $200,000 per year.

Forbes estimates that his and Harris' combined net worth is $8 million, up from $7 million in 2021.

So, for all of Doug's sacrifices for his wife's career – it appears he's doing just fine.