Former Obama White House staff reflects on serving America’s first Black president

Former President Barack Obama, who turned 61 on Aug. 4, remains a luminary figure in politics. His former staff tells theGrio that his legacy will forever be marked in history.

Former U.S. President Barack Obama, who turned 61 on Thursday (Aug. 4), remains a luminary figure in politics. 

U.S. President Barack Obama speaks during a news conference in the Brady Press Briefing Room at the White House December 16, 2016 in Washington, DC. (Photo by Chip Somodevilla/Getty Images)

Not only did he make history as America’s first Black president, inspiring a multiracial and multi-generational coalition of supporters, but he also famously delivered the landmark legislation best known by the moniker with his namesake—Obamacare—providing affordable health care for millions of uninsured Americans.

But for those who worked closely with the 44th president of the United States—namely his Black staff—the Obama presidency meant so much more than simply getting the chance to work inside “The People’s House.” TheGrio was able to connect with several former staffers of the Obama White House, who reflected on Obama’s legacy and what it meant to them to serve the nation’s first African-American commander in chief.

Reflecting on the political rise of Barack Obama during his first presidential run, Deesha Dyer, who served as White House social secretary, told theGrio, “I think for the first time, many people who were turned off by politics or just didn’t know about politics were engaged and excited about President Obama’s campaign and later, presidency.” 

Heather Foster, who joined the Obama presidential campaign early on in 2007 as a volunteer in Chicago, recalled being “really impressed” by the then U.S. senator. “He was on the board of a nonprofit that I interned at initially when I was in college,” Foster told theGrio. 

While Obama may not have been as well known across the country as he was in Illinois at the time, Foster noted that his message of “it’s not about me” but about the collective was what resonated with the then-record 69.5 million voters who cast their ballots for him. “It was about doing something together,” said Foster. 

Former President Barack Obama speaks at a rally to support Michigan democratic candidates at Detroit Cass Tech High School on October 26, 2018 in Detroit, Michigan. (Photo by Bill Pugliano/Getty Images)

The sense of “we’re in this together” was a common theme throughout Obama’s presidency and encouraged his White House team to work diligently and collaboratively to achieve their legislative and policy goals. Most of the White House staff who spoke to theGrio said that signing the Affordable Care Act, also known as Obamacare, into law was by far the most consequential accomplishment of the Obama administration. 

Foster said she is proud of the Obama White House’s work on expanding health care, which eventually “change[d] people’s mindset about health care.” 

“It doesn’t matter where you live—north, south, east, west—it’s now accessible health care with accessible options,” said Foster, who noted that today more Americans are getting screenings and preventing disease by being able to seek regular care. 

“The Affordable Care Act will go down in history as one of the most consequential shifts toward equity the country has made,” said Jesse Moore, who worked as an Obama White House speechwriter and associate director at the Office of Public Engagement. “It’s still marred by politics and misinformation, but there is no denying that it broke a decades-long log-jam of inaction on an issue that will touch every family sooner or later,” he told theGrio. 

Aside from legislative achievements, the former Black staffers also reflected on their fondest memories working inside the Obama White House. For Moore, what made the Obama years so special was the president’s ability to “close any perceived gaps between the commander in chief and ‘the culture.’”

“We were lucky to work for a president who represented both with authenticity and pride,” he declared.

The Obama White House’s engagement with the hip-hop community lent itself to facilitating “real-talk about the power of music in young people’s lives, the future of criminal justice reform, and the relationship between fame and leadership,” said Moore.

He recalled sitting down the hall of the Oval Office with Grammy Award-winning rapper Kendrick Lamar, who he invited to the White House to meet with President Obama. 

President Barack Obama meets with hip hop artist Kendrick Lamar, during an Oval Office drop by, Oct. 19, 2015. (Official White House Photo by Pete Souza)

“Trying to ease any nerves he was feeling, I asked him ‘why he accepted my invite,’” remembered Moore. “He took a beat and answered, ‘it’s for the kids in Compton, really. The president feels like the moon to them. Like, you know you’ll never touch it, so it doesn’t seem real. But those kids know me. So when they see me shake his hand, I think they’ll see that he’s real—and so are they.’”

There’s no question that to millions of Americans, President Obama was larger than life. Foster recalled the frequent fanfare whenever Air Force One touched down in a city. “[We would see] the signs at the airport [and] along the streets welcoming President Obama. Every event you would see the long lines of people willing to stand and listen,” she told theGrio.

But celebrity stature aside, many of the former staff described President Obama as authentic and a family man.

Joshua DuBois, who served as executive director of the White House Office of Faith-based and Neighborhood Partnerships, said one of his fondest memories was teaching Sunday school lessons to the first daughters, Malia and Sasha Obama. The love of family was something that extended beyond the First Family. DuBois recalled proposing to his now-wife on the White House grounds and President Obama going out of his way to call him afterward to express a personal message of congratulations. “It’s about time,” joked Obama.

There was also plenty of family fun and Black cultural moments during the Obama years, recalled Charmion N. Kinder, who worked as an associate at the press office for first lady Michelle Obama, and later as a public affairs appointee at the Departments of Housing and Urban Development (HUD) and Commerce.

“I will never forget the day that I discovered that Mrs. Obama did not need one moment of practice to recall how to play Double Dutch for a Worldwide Day of Play PSA shoot on the South Lawn,” Kinder shared with theGrio. “The president walked out of the Oval Office and asked us what we had going on. And, the camera crew asked if it was a requirement to know how to play Double Dutch to work at the White House.”

U.S. first lady Michelle Obama jump ropes “Double Dutch” on the South Lawn of the White House during an event promoting exercise and healthy eating for children October 21, 2009 in Washington, DC. The Healthy Kids Fair included events on cooking healthy meals and emphasized children getting a proper amount of outdoor exercise each day. (Photo by Win McNamee/Getty Images)

Kinder said that moment brought an “overwhelming sense of being a Black woman in the world who belonged.” She added, “it’s a memory that will stick with me for the rest of my days.”

That sense of belonging and aspiration brought on by the Obama presidency was a common theme shared by the former staffers. All of them expressed deep gratitude for having the opportunity to have served their country and the nation’s first Black president, who they say was and continues to be an inspiring figure. 

“He dared us to remove limits, challenge barriers that prevented humanity from rising to the occasion of living promising and innovative lives, and he dared us to see ourselves centered in the power of our futures,” said Kinder. “His vision and commitment to creating a more perfect union left an indelible mark on the lives of our families—most importantly our nation’s children—and he did so with humor, unflappable grace and respect for all of humanity as a lifestyle. We are all better for his leadership as an example of how to serve.”

In terms of Obama’s legacy, Foster said she believes the former president will always be remembered for “inspiring people to be leaders,” as he did for many Obama White House alumni.

“It doesn’t matter where you’re from, what your background is. If you care about an issue, you can lead on it. That can be in your hometown. That can be as the leader of an organization, leader of a firm, leader of a company,” added Foster. 

DuBois, Obama’s former director of faith-based and neighborhood partnerships, said he believes his legacy will be known as “one of America’s greatest presidents, who made life better for millions of people and expanded the sense of possibility for millions more.” He added, “He was a healer in tough times—like after Charleston—and a hopeful voice charting our future.”

Kinder noted that former President Obama is continuing to empower and connect people to “change their world,” through his and Mrs. Obama’s Obama Foundation, and the foundation’s various leaders programs, including Girls Opportunity Alliance, My Brother’s Keeper Alliance and the Obama Foundation Fellowship.

Former U.S. President Barack Obama and his wife Michelle close the Obama Foundation Summit together on the campus of the Illinois Institute of Technology on October 29, 2019 in Chicago, Illinois. The Summit is an annual event hosted by the Obama Foundation. (Photo by Scott Olson/Getty Images)

She also mentioned that Obama’s presidential center, which is still being built in Chicago, “represents an opportunity to build a world-class museum and public gathering space that celebrates our nation’s first Black first family, while uniting a new generation of leaders that can come together to move progress in the world forward.”

Dyer, Obama’s former social secretary, said President Obama will always have “the responsibility of being involved in social and political issues, which she noted, “is one that he’s had since community organizing in Chicago.”

Moore, the former Obama White House speechwriter, said Obama “remains the trusted, earnest voice we need in moments of darkness,” adding, “He’s still a voice I hope to hear when the country feels off-kilter or under threat.”

Gerren Keith Gaynor

Gerren Keith Gaynor is the Managing Editor of Politics and Washington Correspondent at theGrio. He is based in Washington, D.C.

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