‘I ran the White House lives of the Obamas for more than two years’

Deesha Dyer was unlike any previous White House social secretary. Her new memoir reveals what went on in the East Wing.

President Barack Obama and First Lady Michelle Obama with Social Secretary Deesha Dyer at the White House in 2015. Picture: Pete Souza/White House

The arrival in 2017 of Donald Trump to take occupancy of the White House was, of course, marked by a bit of protocol-defying trouble. For Deesha Dyer, it was to be a final moment of drama in her role as the White House social secretary for the Obamas.

To supervise this crucial encounter, Dyer had been hiding in the fold of a curtain at the front window, when she spied Melania appearing out of the car with an enormous turquoise Tiffany & Co box. “I was so mad … so mad,” Dyer writes in her new memoir, Undiplomatic. “I’d confirmed with the Trump advance team there would be no gift exchange.”

Not only did Michelle Obama have nothing to offer in return – she’s heard saying in surprise, “You brought gifts?” – but she was stuck looking awkward on live TV, moments before the prospect of goofily advertising Tiffany by holding a branded box in the official photographs. Of such scenes a social secretary’s nightmares are made.

Instead Barack Obama is heard on camera saying firmly to the Trumps, “No, no, we will take care of the protocol”, removing the gift from his embarrassed wife. At this point Dyer senses her boss needs her: she rushes to the other side of the door, through which Barack then pushes the box into her hand. This little moment caused a big talking point: Michelle later even gave an interview to talkshow host Ellen DeGeneres about it.

Moments such as these will some day surely inspire a Netflix series – perhaps titled “East Wing”, after the part of the White House where the social secretary is based. Dyer’s role was not overtly political, compared with the machinations of the West Wing, but in practice it could bring an equally painful collision of the personal and the professional. Never more so than at her first trial by fire in 2015, just months into her tenure.

In the space of a week there was a visit from the Chinese premier to arrange, a state dinner and a visit to a United Nations summit. All the while Dyer was harbouring a secret unknown even to the Obamas. It was a pregnancy she needed to abort.

Although the clock was ticking, Dyer felt she had to delay the operation because, irony of ironies, she also had to orchestrate a visit from Pope Francis – which included about 12,000 Catholic supporters massed on the South Lawn. What cosmically fateful timing, I say to her when we meet at Gunpowder, a restaurant in Soho.

“It was terrible,” Dyer says. She only informed the Obamas much later, when their relationship was cemented into the warm familiarity that continues to this day, as she still works for the couple on an ad hoc basis. “When I eventually told the president and the first lady, they were like, ‘We would never have wanted you to … please go home, take your time’.”

Everything about Dyer’s rise to one of the most high-status jobs in Washington is extraordinary: she was a White House intern at the unusual age of 31 (most White House interns, such as the most famous, Monica Lewinsky, are barely in their 20s) and was hand-picked for her top role by Michelle Obama.

As we talk Dyer, now 47, in London with her husband, is courteous to a fault, her charming self-deprecation vying with impostor syndrome. Yet in Washington she said she felt shunned. It wasn’t just that as a black woman she had to be mindful that any strong opinion, necessary in a leader, would attract the stereotypically “black woman” slur of “difficult”. “Mrs Obama actually told me, ‘Sometimes you have to curb it to get things done in the long run’,” Dyer says.

The social secretary is responsible for every event that takes place in the White House grounds, other than in the Oval Office and press room. This could be anything from the traditions of the Easter egg roll or the Thanksgiving pardon of one lucky turkey – a chance for the first family to showcase their softer side – to events orchestrating hundreds of dignitaries with world-class egos. The social secretary, wielding the White House calendar and guest list clipboard, has the power to shape its public face. It’s a symbolic role?

“Very much so,” Dyer says. “It has to be, because you are the person that executes the vision for the first lady and the president. So everything that happens in 1600 Pennsylvania Avenue is under your jurisdiction.”

President Barack Obama's Social Secretary Deesha Dyer. Picture: Instagram

‘I think that if we didn’t have a Barack Obama, we probably wouldn’t have Donald Trump right now,’ says Dyer. Picture: Instagram

Her post had traditionally been held by someone of the political belle monde who could play their networks like a violin. Yet Dyer grew up working class and was sent to a boarding school for disadvantaged students, where she lost confidence in herself. She dropped out of college and spent her 20s in Philadelphia as a hip-hop reviewer and community AIDS activist, supporting herself by working as a secretary.

After catching Obama fever, she applied for the White House internship despite knowing most candidates would be from an Ivy League university and a decade her junior. She parlayed this chance into a series of hard-won promotions. Eyebrows, she says, were raised in Washington society circles. “Honestly, it wasn’t racism, a lot of it was more about social status and classism.”

Grand dames would suggest she replace her gold hoop earrings for pearls, and donate to her their ancient designer handbags as if she were a “charity case”. Yet the Obamas liked that she, like Barack Obama, had been a community activist, and that her cultural landscape was modern and youthful. Her remit as social secretary was to open up the White House, to make democracy feel more inclusive. In his first term Trump had a social secretary; so far during this term there is, unusually, no social secretary.

“I don’t think they see a need for the role to be as big,” she says. “Also I don’t think the First Lady is at the White House much.”

Would someone from her background be hired at the White House now, I ask. “Absolutely not.” The Obamas wanted, she says, for the White House to be the “People’s House”. What does Trump want the White House to be? “The Rich People’s House,” she fires back.

Meeting Pope Francis at the White House in 2015. Picture: Pete Souza

Pope Francis was arriving on the Wednesday. That weekend Dyer found out she was pregnant; on the Monday she took time she felt she couldn’t spare to walk from the White House to the clinic for a pre-abortion check-up. The receptionist was harried, staff were running late and Dyer started to worry about getting back to her duties. Dyer joked with the abortion clinic staff: “Do you want tickets to come see the pope at the White House?” The room filled with dark laughter. After the appointment she dried her tears and got straight back to work, only pausing to run to the bathroom with morning sickness.

On the eve of the pope’s visit, Dyer slept on a camping mat on the floor of her White House office, as she did on high-pressure occasions, and that week was classed by The New York Times as an unprecedented “Super Bowl” for any social secretary.

She could hear the buzz of crowds camping outside. Three hours before the visit her dress, picked a month before, ripped under her new pregnancy weight, and she had to rush to the White House seamstress for repair. After every detail of the day went to plan, Dyer was almost ready to relax when Barack Obama gestured her over. He was chatting informally with the pope and told him Dyer had made “this all happen today”.

The pope enclosed her hand in both of his for a long five seconds. The feeling, she wrote in the book, “was overwhelming and confusing”. Her abortion was scheduled for a week away, after her first state dinner “with an uninvited guest in my belly”.

“In the picture,” Dyer tells me of the photo of her with Obama and the pope, “you can see the dress is way too tight. I look at it now and think how much I was going through, unbelievable.” She was ashamed for having an unwanted pregnancy, but she felt also filled with God’s grace as the pope told her, “Thank you”.

Obama and Dyer in the Oval Office in June 2015. Picture: Pete Souza

Since leaving the White House she has refocused on her community outreach work. She looks back at her White House era in wonder “that the country rallied around a black man like that. Still, to this day I think, wow, did that even happen?”.

“It makes me extremely sad,” she says. “I think that if we didn’t have a Barack Obama we probably wouldn’t have Donald Trump right now … That scared America. Unfortunately they will do all they can to make sure that that never happens again.”

Yet it was the honour of her life to see that history up close. To unwind dancing to Beyonce with Barack and Michelle after the Christmas parties, to be on the last Air Force One flight with the Obamas leaving the White House for the final time, where they spent hours drinking and reminiscing.

By night Dyer always respected the White House as a private family home: after hours she’d keep a respectful distance in her office as the family went to its movie theatre with the dogs, the Obama girls had birthday parties, or their grandmother, Marian, “wanted to say hi to the chefs”.

I ask her what she missed about the White House. Dyer says whenever she needed energy in her long days she would stand outside her office, which happened to be right next to the public entrance. “People were just so enamoured with it,” she says, and the Obamas enjoyed surprising them on tours. “Especially watching elderly black people, who had fought for civil rights, and thought they would never live to see a black man as president.

“Kids loved him too. Just to see the look on their faces kept me energised and joyful, because I was part of the community that elected him with those same bright eyes … That pure feeling I think was unique to us. There was nothing like it. Nothing like it.”

The Times