The Post-White House Transformation Of The Obama Family

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Former President Barack Obama wrote himself into the history books when he beat his opponent, John McCain, in 2008 to be elected America's first Black president. The Obamas — a family that includes patriarch, Barack, matriarch Michelle Obama, and their daughters, Sasha and Malia Obama — then settled into the White House and turned it into an interior design marvel with the help of Los-Angeles-based designer Michael Smith.

The Obama family was already used to luxurious living since they previously stayed in the posh neighborhood of Kenwood on the Southside of Chicago (the Obamas now own three homes). As such, their transition to the White House was pretty smooth on all but one day: the beginning of their stay. "That first night, you kind of wake up with a startle then say to yourself, 'My goodness, what am I doing here?'" Barack recalled (via YouTube). "Every day, although you consider it the place you live, I think you're very mindful that this is a place of history. That this is a place that belongs to the people and to the country ... While you're here, you may be part of the first family, but once your term's up you're going to be a citizen once again."

During their time at the White House, the Obamas made it accessible to the public in a way that it hadn't been before. Michelle hosted the Girl Scouts on the South Lawn in July 2015, and a month later, entrepreneurs got to pitch their ideas on the White House's inaugural Demo Day. Following the election of Donald Trump as president in 2016, the Obamas exited the White House. Barack, his wife Michelle, and their children have since experienced major changes in their personal and professional lives.

When the Obama family left the White House, they reportedly rented a mansion in the Washington, D.C. neighborhood of Kalorama, which isn't far from their former Pennsylvania Avenue address. The Obamas eventually purchased the said mansion for a reported $8.1 million, making them neighbors to an elite crowd, including first daughter Ivanka Trump and former Secretary of State Rex Tillerson.

The home, which was previously owned by Joe Lockhart (who was former President Bill Clinton's press secretary), helped the Obamas write themselves into the history books yet again by staying in D.C. post-White House. The last known president who made a similar move was the late President Woodrow Wilson, whose D.C. home has since been made open to the public.

The Obamas' transition from the White House to living as citizens was strange, at least according to Michelle Obama. "It was odd coming down a different street and parking through a different set of barricades, because we still had barricades," Michelle recalled in a chat with "Moments That Make Us." "We still had Secret Service, but I had a front door. It's, like, the little things [that matter] ... I had a front door that I could open." At the time of the Obamas' move, their youngest daughter, Sasha Obama, was still schooling in the D.C. area. Sasha eventually graduated from Sidwell Friends School in June 2019 and was set to attend the University of Michigan.

Prior to their exit from the White House, the Obamas were vocal about how they would spend their first few months away — and it had everything to do with well-deserved leisure. "We're gonna rest a second," Michelle Obama said in her and Barack Obama's final joint interview as a presidential couple with People. "We're gonna take a breather, you know. As I told all of our staff here, it's time for us to tap out for a second. People need time to refresh and to reflect."

Of course, the Obamas led by example. They first had a short vacation in Palm Springs as a family. In February 2017, Barack and Michelle accepted a challenge to kiteboard and seek adventure in the British Virgin Islands following an invite by billionaire businessman Richard Branson. The following month, it was reported that Barack had booked a month-long stay at Marlon Brando's private resort at the Tetiaroa Atoll in French Polynesia.

In May 2017, the Obamas were still on a traveling spree, as Barack and Michelle reportedly had a six-day stay in Tuscany, Italy, all while protected by high-level security detail. In June 2017, Barack and Michelle were joined by Sasha and Malia Obama on a trip to Bali, Indonesia, a Southeast Asian country in which Barack spent a good chunk of his childhood. The former first family went river rafting in Bongkasa Village, had a fun walk through rice fields, and visited a museum during their five-day stay.

Malia Obama graduated from Sidwell Friends School in June 2016, months before Barack Obama's second term in office came to an end. A month prior, the White House released a statement announcing that Malia would enroll in her parents' alma mater, Harvard University, in 2017. Malia took a gap year, during which she set her sights on the film business. She fed her passion for filmmaking by attending the Sundance Film Festival in January 2017 and worked as an intern for The Weinstein Company in New York.

Malia finally joined Harvard in August 2017 as a history major, and of course, her family was there to help her move into her dorm room — all but former President Barack, who didn't offer a helping hand. "Michelle, she had like a cleaning glove, one of those yellow ones, she's scouring the bathroom," Barack revealed in a chat with "My Next Guest Needs No Introduction with David Letterman" (via CNN). "Sasha ... was helping make the bed and fold clothes ... and I was basically useless." Barack only had a 5-minute task of assembling a desk lamp, but the activity turned out to be a Herculean chore.

Malia eventually settled into Harvard, and her romantic life soon took center stage. She reportedly began dating Rory Farquharson – a former student of the Rugby School in England — with whom she was pictured kissing at a Harvard-Yale University game in November 2017. The following year, Malia and Rory were photographed shopping in New York City, and although the timeline of the couple's ultimate breakup is not clear, Malia was seen on what appeared to be a date with producer Dawit Eklund in August 2022.

The Obamas have a long history with the Carters — singer Beyoncé Knowles and her renowned hip-hop artist husband, Jay-Z. When Barack Obama first assumed the presidency, Knowles serenaded him and Michelle Obama as they had their first dance at the Neighborhood Ball. Years later, when Barack was eyeing a second term in office, Jay-Z and Beyoncé helped by holding a fundraiser at the former's 40/40 club. The duo managed to raise $4 million by charging attendees a $40,000 entrance fee, and it goes without saying that the former president had kind words for them.

Speaking at the event, Barack said of the "Halo" singer, per The Hollywood Reporter, "Beyoncé couldn't be a better role model for our daughters because she carries herself with such class and poise and has so much talent." Barack also remarked that he had a connection to Jay-Z because, "We both have daughters and our wives are more popular than we are."

It therefore made sense for the Obamas to make stops at Beyoncé and Jay-Z's "On the Run II" tour in 2018, not once but twice. In mid-July 2018, Michelle was seen in the company of Sasha and Malia during the tour's Paris stop. Fan videos from the concert showed Michelle dancing next to Beyoncé's mom, Tina Knowles. Later that month, Michelle and Barack attended another "On the Run II" concert in Landover, Maryland, where they were filmed dancing to Jay-Z and Kanye West's mega hit "Ni***s in Paris."

Michelle Obama published her first book, a memoir dubbed "Becoming," in November 2018. In the body of work, the former first lady went into detail on different phases of her life, including her childhood, motherhood, and her time at the White House. In her writing process, Michelle shattered the myth that only the glamorous bits of her life made for a good narrative. "Every part of our stories, no matter how small or simple, has meaning and value," she said (via Facebook).

Within the first 15 days of its release, "Becoming" had sold two million copies in North America and was flying off the shelves worldwide. Speaking on the memoir's groundbreaking success at Oprah's 2020 Vision Tour, Michelle said, "So many people saw themselves in my story. It's also a time for owning our stories, and I think that's part of what resonated with people ... I embrace every aspect of who I am because, as I've said, I like my story. I like all the highs and lows and the bumps in between."

In 2019, Michelle went on a nationwide book tour with a star-studded moderator lineup , including television hosts Jimmy Kimmel, Conan O'Brien, and Stephen Colbert. The book tour was aired as a documentary on Netflix in 2020, and needless to say, that wasn't her only win that year: "Becoming" earned Michelle her first Grammy award in the best spoken word album category. In November 2022, she became a two-time author, following the release of her second book, "The Light We Carry: Overcoming in Uncertain Times."

Prior to leaving the White House, former President Barack Obama was a three-time author. His first book, "Dreams from My Father: A Story of Race and Inheritance," was published in 1995, while his second book, "The Audacity of Hope: Thoughts on Reclaiming the American Dream," was released in 2006. He also wrote an illustrated children's book in 2010, "Of Thee I Sing: A Letter to My Daughters."

Four years after he left the White House, the former president published his third book, titled "A Promised Land." The memoir's writing process, he said, was modeled after the work of celebrated novelist James Baldwin. "If you ask me what's a book that taught me to think about how I would like to write [and] what I would aspire to write, even though I can't write that good, it'd be probably 'The Fire Next Time' by James Baldwin," Barack told The Washington Post.

In "A Promised Land," Barack detailed multiple aspects of his life, including his quest to find an identity, highlights of his presidency, and his take on the global financial crisis. Of course, the book topped the best-sellers list; "A Promised Land" sold an astounding 3.3 million copies after being on shelves in the United States and Canada for one month. Still, he wasn't done just yet. In 2021, Barack collaborated with rock singer Bruce Springsteen to release the joint body of work, "Renegades: Born in the USA." The duo first crossed paths in 2008 and formed a bond that has stood the test of time. Their book was named after a joint podcast that bears the same name.

Former President Barack Obama's love for basketball dates back to Punahou School in Honolulu, where he was a not-so-popular member of the basketball team because he had a feud with his coach. Barack, popularly known as "Barry" in his heyday, was an activist at heart who negotiated for more playing time for himself and his fellow teammates.

When he became president, Barack famously coached his daughter, Sasha Obama's fourth grade team, the Vipers, who played for Sidwell Friends School. Barack had noticed that the team's basketball coaches weren't exactly bringing their A-game to the table, and he took on the role, eventually leading the Vipers to win a championship. Barack has often shown his passion for the sport by showing up to NBA games. The former president even put together a dream team he would like to see on the court, which included six-time NBA champion Michael Jordan, LeBron James — who has the most points in the league at the time of writing — former Los Angeles Lakers forward Magic Johnson, Steph Curry, and Hakeem "the Dream" Olajuwon.

With all of this passion, it wasn't surprising when Barack became a strategic partner with the NBA's Africa division in 2021. "The NBA has always been a great ambassador for the United States — using the game to create deeper connections around the world, and in Africa, basketball has the power to promote opportunity, wellness, equality, and empowerment across the continent," Barack said in a statement to the league. "I've been impressed by the league's commitment to Africa, including the leadership shown by so many African players who want to give back to their own countries and communities. That's why I'm proud to join the team at NBA Africa and look forward to a partnership that benefits the youth of so many countries."

Malia Obama graduated from Harvard University in 2021. She then moved to Los Angeles to pursue a career in television writing and filmmaking. Malia collaborated with actor Donald Glover on her first short film, "The Heart," which premiered at the Sundance Film Festival in January 2024. She became roommates with her sister, Sasha Obama, who transferred from the University of Michigan to the University of Southern California (USC).

For mom, Michelle Obama, the pair's decision to stay together was surreal. "You try not to react too much because it's like, you don't want to go, 'Oh my gosh, I'm so happy for you!' because then they think, 'Well, maybe this is not a good thing if my mom likes it,'" Michelle recalled in a chat with People. "So I just said, 'Okay, well that's interesting that you guys are going to try living together. We'll see how it goes.'" Away from studies and work, the Obama sisters are quite a social brood and continue to live lavish lives. Sasha and Malia are no strangers to the Los Angeles party scene and often interact with young celebs in entertainment. In August 2023, the duo was pictured leaving a Drake afterparty, and nearly two years later, they both showed up to singer Destin Conrad's album-release party.

Malia and Sasha — who graduated with a degree in sociology in May 2023 — stay in contact with their parents via a group chat in which Barack Obama is surprisingly the most active participant. "He's still typical [Dad]. You have these weird panic thoughts that your girls are out living in this messy world. And so, you think about crazy things you want to make sure you tell them," Michelle told People.

Rumors of trouble in Barack and Michelle Obama's marriage took the internet by storm in August 2024 when tabloids alleged that the former was having an affair with actor Jennifer Aniston. The rumors had actually started as a joke in 2014 after The Economist lightheartedly published a hypothetical fictitious story linking Aniston and Barack together. When Aniston was confronted about the alleged affair on "Jimmy Kimmel Live!," the "Friends" star revealed that she had only met the former president once in her lifetime and hilariously said, "I was not mad at it [the rumor]." As for whether there was any truth behind the rumors, Aniston vehemently denied the claims, saying, "That is absolutely untrue."

The rumors spread like wildfire again when Michelle was noticeably absent at former President Jimmy Carter's funeral and President Donald Trump's inauguration in January 2025. The power couple was said to be headed for divorce, which was gossip that Michelle dismissed with a tirade during an episode of the "IMO" podcast.

The former first lady explained that she skipped the inauguration for her own personal reasons. "My decision to make choices at the beginning of this year that suited me were met with such ridicule and criticism," she said (via Instagram), and continued, "People couldn't believe that I was saying no for any other reason, that they had to assume that my marriage was falling apart ... I'm here really trying to own my life."

Michelle Obama and her brother, Craig Robinson, launched the "IMO" podcast in March 2025. The podcast joins the long list of shows under the belt of Higher Ground Productions, which Michelle and Barack Obama founded in 2018. In her promo of the first episode of the podcast via Instagram, Michelle reflected on her relationship with Robinson, which has remained solid throughout different seasons of her life — her childhood in Chicago, college, the White House, and life after Barack's presidency. "For over six decades, we've been each other's sounding board — and now, we can't wait to be yours, too," Michelle wrote, in part, in her caption.

The podcast has since had numerous guests with whom Michelle and Robinson have tackled different issues. In a chat with entertainment powerhouses Damon and Marlon Wayans, Michelle and Robinson covered the Wayans family's rise to the top, parenting a transgender child, and their association as siblings. And when entrepreneur and philanthropist Tina Knowles made an appearance on a live version of the podcast, she and Michelle discussed several topics, including motherhood and entrepreneurship.

Michelle and Robinson's podcast features light and fun moments, too. When billionaire Airbnb co-founder Brian Chesky revealed he was single and had listed his house on Airbnb, Michelle was a bit cheeky, but she also wanted to know the best dating advice he'd receive from her husband, Barack. Chesky made a profound recollection: "It's not a checklist ... It's not necessarily what you think you are looking for. And, you're not dating a checklist, you're dating a real person."