It’s Deesha Dyer’s first week in a new job that nothing in her back story suggested she would ever hold: White House social secretary.
The job has historically been the province of upper-class white women with pedigree, connections and political networks. Dyer arrived in Washington with none of these.
She was a girl from a hard-knock neighborhood in West Philadelphia who dropped out of college, got a 9-to-5, developed a side-hustle writing about Philly’s hip-hop and soul scene, went to community college, and at age 31 became a White House intern. It’s a résumé that would be highly unusual even among the more eclectic guests at White House state dinners — and now Dyer will be the woman who organizes them.
She is only the second black woman to serve in the role, responsible for planning every event held at the White House and executing a vision that reflects the Obamas’ style. “I’m excited about being able to bring people in here, and to make the White House as public as possible, and make sure that I am a warm face, I’m comforting and I’m a good host,” Dyer said in an interview this week.
She is definitely a fresh face — who looks younger than her 37 years — but Dyer is no Ms. Smith goes to Washington. For the past two years she served as deputy to her predecessor, Jeremy Bernard. She’s described as sharp, ambitious, an overachiever whose network was built within the confines of the Obama White House, where she is generally beloved, cited for her “positivity” and work ethic.
“She was a force in the best way possible,” said Alyssa Mastromonaco, President Obama’s former deputy chief of staff for operations and Dyer’s boss during her 2009 internship.
Admirers of the Obamas, who selected her for the new job, like to highlight the ways Dyer symbolizes their pledge to open the White House to young people who would not ordinarily come there, a world apart from the usual Washington social set.
The Obamas’ first social secretary, Desirée Rogers, struck a blazingly glamorous figure — perhaps distractingly so — and left after just over a year. The second, Julianna Smoot, was an adept political fundraiser with a knack for cultivating power players. Bernard, the first man and openly gay person in the role, was a longtime political supporter of the Obamas.
Dyer has been more of a worker bee. But in addition to valuing symbolism and competence, the Obamas are known to treasure loyalty, and the closing months of a second term are traditionally the time for an administration to reward the faithful with the big titles that can launch them onto a high-profile career track, post-White House.
As anyone who knows Dyer will tell you, her past experience and present position work in an unexpected harmony. She founded a mentorship program in Philadelphia and now helps to plan White House workshops for students.
At a film workshop in late 2013, Dyer decided to start things off by leading the visiting high school students to the south balcony of the White House to watch the president’s helicopter take off, before partnering them with Hollywood VIPs for the day’s seminars.
“We thought about what they usually don’t get in school. They get art. They get painting. This is different,” Dyer said that day as she rushed from room to room in pumps that by the end of the day gave way to sensible flats.
On other occasions, some of those Philly musicians Dyer used to write about during her journalism years have ended up performing at White House functions.
“The White House is very much a place where you could easily get stuck in doing what has always been done, but Deesha thinks outside of that,” said Danielle White, the president’s former director of scheduling and a friend of Dyer’s.
The outsider has become the ultimate insider. And Dyer plans to bring even more outsiders in.
“Mrs. Obama has always talked about having a very open White House and to make sure that it is the ‘People’s House’ and that it stays that way,” Dyer said. “They put me in this position to continue to bring people into the house and as many people as possible.”
Dyer is from Philadelphia, but she spent her formative years amid rolling fields in Hershey, Pa., at the Milton Hershey School, a full-scholarship boarding school founded by the chocolatier a century ago. With a $10 billion endowment, the school admits students from low-income families based on factors that include their level of poverty and living conditions, with priority given to students from Pennsylvania.
Dyer’s parents, Diana and Isaac Dyer, enrolled her and her older brother, Isaac, in the school. Dyer spent her middle and high school years living in a home with other students and house parents, who assigned chores — cooking, dusting and the like.
“Looking back on it now is an emotional experience,” Dyer said. “I lived with 16 girls all my life and was able to work with different people, different personalities. It was a great place to grow up.”
Dyer graduated from Milton in 1995. In 2005, the school gave her an alumni award for community service. But those years in between were marked by detours. She started college at the University of Cincinnati, where she was in the school’s color guard. But despite a financial lift from Milton, which provides scholarships to its graduates, she found university life unaffordable. She dropped out and returned to Philadelphia without completing her degree.
“Cincinnati is a beautiful place, and I had a great group of friends,” Dyer said. “I just wasn’t prepared financially for college at the time.”
Back home, Dyer worked as an assistant at a real estate company and traveled abroad, flying to Europe and Mexico.
“It was a see-what’s-out-there, late-20s kind of travel,” Dyer said. “I would go over for about two weeks at a time and then come back here and work for a little bit, then save up enough to go somewhere else.”
She also started a hip-hop HIV-awareness program, passing out fliers and condoms at local clubs, and for seven years, she wrote music previews for local publications, including Philadelphia’s City Paper. The young freelancer proved that she was tuned in to the hip-hop scene, said Patrick Rapa, the paper’s music editor.
“It was almost entirely writing about independent and lesser-known acts,” Rapa said. “She had her ear to the ground, and she was very persistent” — but not a pest, he said. She became his go-to hip-hop writer at a time when Philly music was about to explode nationally.
“It was just so rich. It drew a lot of us in,” recalled MSNBC reporter Trymaine Lee, a Hershey School classmate who also covered the music scene then. They saw the rise of Jill Scott, the Roots and band leader Questlove, then a DJ at a local club. Old-school Philly hip-hop remains the music Dyer turns to at the end of a long day.
Dyer remembers that time in her life fondly, but freelance writing did not pay the bills, and real estate was not her passion. At 29, she returned to college and earned an associate degree in women’s studies. While looking for opportunities for a group of girls she was mentoring, she came across an application for a White House internship and applied.
She joined the administration at a time when the clique of young campaign grunts who had sweated it out together for the president were settling into their White House jobs. She was 32 and had to figure out her place among them.
“We were a group of people who had worked together through the campaign and were coming into the White House in the most emotional of circumstances, and she fit in,” recalled Mastromonaco, the former deputy chief of staff for operations. “From the minute she got here, we just knew she was one of us.”
At the end of her White House internship, Dyer was named associate director for scheduling correspondence and then promoted to hotel program director, traveling with the president and first lady and planning lodging for the White House entourage. Bernard brought her onto his team in 2013, and she often functioned as his liaison or would oversee one event when he was preoccupied with a conflicting one.
I first met Dyer when the first lady’s press office invited me to hang with her behind the scenes at the 2013 film workshop. The close media access to a member of the East Wing staff was unusual, but Dyer seemed comfortable as I followed her around with my reporter’s notebook. Months later, when I ran into her on the street and waved hello, she stopped to give me a hug and chat me up.
“That’s how I am all the time,” she said later. “I love meeting new people. I love meeting different people.”
“As soon as we met, she hugged me,” Bernard told Vogue this year, describing Dyer as a serious-minded colleague with a great sense of humor. “And she’s incredibly warm.”
Her friends ascribe almost magical powers to her. She is not just a routine volunteer at Carpenter’s Shelter in Alexandria, but an all-star one who whips up hot meals such as chicken and waffles or hot dogs and hamburgers for the 60 homeless men and women there while other volunteers fall back on a vat of pasta, said a coordinator there.
Other pals swear that she is capable of stretching time. She mentors several girls in different cities. And last summer in Philadelphia, Dyer was among a group of black women who founded beGirl.world to encourage teenage girls to travel abroad.
Between her 14-hour days at the White House, she makes time to work out, with yoga classes or SoulCycle. And once or twice a year, Dyer serves a homemade brunch outdoors at her Capitol Hill home for a couple of dozen women from the White House. The group includes low-level staff members, especially young black women, as well as senior staffers, including the first lady’s chief of staff, Tina Tchen.
“She is bringing this group of women together in a social way that, outside of work, would probably never have been together,” said White, the former director of scheduling. “And she’s a pretty good cook.”
Dyer is not known to be personally close to the first lady, but she has earned Michelle Obama’s trust, according to a former East Wing staff member, who did not want to go on the record discussing internal White House dynamics.
“In that position, the first lady has to have absolute confidence that you’re on your game,” the staffer said. “If it all goes downhill, everyone will wonder how did the first lady fail. They won’t think the president was a bad host. They will think the first lady was a bad hostess.”
If Dyer is feeling pressure, she will not admit it. When asked about dealing with people who make certain assumptions about her unconventional résumé, she brushes it off.
“There are preconceived notions in life in general — whatever you do, whatever position,” Dyer said. “We always deal with those, [but] this role has been held by people who are all different, and they have all brought their own things to this role, so I look forward to doing that as well.”
Dyer said she sees Bernard as a model. He, too, was a historic pick for the job, and he also has no bachelor’s degree and has said he would never have expected to be appointed to the position. But, by all accounts, he was a success, overseeing events large and small with finesse while remaining in the background.
Already, her schedule is packed. For Friday, she was planning to oversee Michelle Obama’s annual Mother’s Day tea for military moms. She’s working on the Kids State Dinner and the Fourth of July picnic on the White House grounds.
And, of course, she is also planning the state dinner for China in the fall — the ne plus ultra gala for every White House social secretary.
“I’m excited about that — although it is not for a while,” Dyer said. “I’m already thinking about my outfit and everything we need for the event.”
Alice Crites contributed to this report.