Former Second Gentleman Doug Emhoff Plays Second Fiddle As His Law Firm Bows to Trump

After his unsuccessful bid for the title of “First Gentleman,” Doug Emhoff, the spouse of former Vice President Kamala Harris and referred to by Jen Psaki as someone who is changing the traditional views of masculinity, had to step up and return to work just like everyone else.

Cue the sad trombone.

With a background as a well-known attorney and having been part of a previous unsuccessful presidential administration, his resume still carries weight in the legal world. This could be the reason why Willkie, Farr & Gallagher wasted no time in offering him a partnership shortly after the Biden administration left the White House.

This is the same firm that recently chose to cut a deal with President Donald Trump over their prior “work” targeting him and anyone connected to him. Even through 2024, Willkie Farr made it their mission to harass and bankrupt former New York City mayor and Trump ally Rudy Giuliani. No longer; Willkie Farr will now give pro bono services to the Trump administration and agreed to drop DEI initiatives from their employment practices. 

Apparently, this did not sit well with Emhoff, who may have gotten ahead of his skis when he tried to stop his firm from striking the deal. 

At a $600-a-plate dinner (the starting bid), Emhoff expressed his displeasure. 

Emhoff is a partner at Willkie Farr & Gallagher LLP, which this week agreed to a deal with President Donald Trump, which the president said includes the firm providing at least $100 million in pro bono legal services throughout his second term.

It’s the third example of a high-profile firm cutting a deal with the White House as Trump has targeted firms that have done work with his perceived political enemies.

Emhoff told the crowd at the Annual Dinner Gala for the legal aid group Bet Tzedek he had told the firm he wanted to fight the threat of an executive order he found unconstitutional but had been overruled, the sources said.

Welp, now we know that Emhoff’s greatest currency is as window decor, and not much else. It’s amazing what happens when you no longer have the privileges of being the Second Gentleman of the United States. One moment you’re prancing before paid-for crowds and attempting to convince folks of your masculinity. The next, you’re complaining at an expensive-plate dinner that barely anyone has heard about that your law firm partners care little about your input.

Willkie’s pro bono work in recent years has been especially attention-grabbing because it included a defamation win against Rudy Giuliani following his work for Trump after the 2020 election.

Willkie had provided representation to two Georgia poll workers who a jury ruled had been defamed by Rudy Giuliani, Ruby Freeman and Shaye Moss, awarded a $148 million defamation verdict.

I worked for a long time in this industry, doing IT and training, and this I know: lawyers are horrible money managers and are always scratching for more. Which means even the toniest of them have to rake in as much money as they can, every chance they can. Willkie Farr & Gallagher LLP knows it’s a losing money proposition to oppose a sitting president who has pretty much been Teflon Don with the majority of these personal, and some presidential, legal challenges.

Since Willkie announced their agreement with Trump, they’ve been bragging about their “new highs on revenue,” and obviously feeling no pain over their decision.

Dougie, on the other hand…

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