Inside Jenna Bush Hager's Sweet Bond With Fellow First Daughters Malia and Sasha Obama

Just a few women understand the delicate balancing of living your life while your dad is president. Jenna Bush Hager offers a peek inside the "sisterhood" she shares with the Obama sisters.

By Sarah Grossbart Nov 25, 2020 8:00 AMTags
Watch: Savannah Guthrie Is Godmother to Jenna Bush Hager's Son

Sometimes bipartisanship begins in the smallest of ways. 

Because there, amid the discord and rancor that has dominated the past several weeks, months and years, really, was a soothing balm from former first daughter Jenna Bush Hager

Three days after Joe Biden was declared the winner of the 2020 presidential election, when it became clear that the idea of a peaceful transition between administrations had been sweetly naive, the Today co-anchor decided to remind her 1.2 million Instagram followers about the November day in 2008 when she drove back to Washington, D.C., after a day of teaching in nearby Baltimore so that she and twin sister Barbara Bush could show Malia and Sasha Obama the bannister in the White House that would provide the most satisfying slide. 

The twentysomething hadn't really lived in the world's most famous address for any long stretch of time, having spent most of father George W. Bush's two terms at college in Austin, Texas, before living on her own in Maryland. 

Malia Obama and Sasha Obama Over the Years

But after years of holidays there and summer breaks, not to mention hide-and-seek-filled visits when grandfather George H.W. Bush was in the Oval Office, she and Barbara were well-versed enough to share "all the secrets of the White House we loved as little girls—the best hiding spots, the movie theatre, and bowling alley," she wrote.

The grand finale: Taking Malia, then 10, and 7-year-old Sasha to "our rooms that would soon be theirs."

A welcome into the club, if you will. 


Because of all her titles—television host, author, magazine editor-at-large, mom of three with husband Henry Hager—Jenna takes her role as elder stateswoman in the First Daughter sorority quite seriously. 

And the reason why may just be tucked into the 768 pages of former President Barack Obama's recently released book. Speaking on his entree into the most high-profile job he'd ever hold, the author revealed how welcoming his predecessor had been. 

"Whether because of his respect for the institution, lessons from his father, bad memories of his own transition (there were rumors that some Clinton staffers had removed the W key from the White House computers on their way out the door), or just basic decency," he wrote, "President Bush would end up doing all he could to make the eleven weeks between my election and his departure go smoothly."

For Jenna, that meant taking an evening to make 1600 Pennsylvania Avenue's youngest residents feel comfortable in their new home. Or in the years after, to vigorously defend them anytime they were judged for making attempts at living relatively normal lives.

And should anyone come for her pal Chelsea Clinton, well, they should expect much the same response from the 39-year-old, celebrating her birthday Nov. 25. "There is a sisterhood," Jenna explained to Andy Cohen on Watch What Happens Live in September of their unbreakable bond, "because it's so few of us that we know what it's like and the beauty of it and living history and also some of the difficulties."

Which, raise your hands if you remember when Jenna was naive enough to think she could get away with using a fake I.D. It's almost endearing to think that then-19-year-old Jenna (cited for misrepresentation of age by a minor for trying to order alcohol at an Austin Tex-Mex eatery in April 2001) and Barbara (cited for possessing alcohol as a minor thanks to her "partially consumed" margarita) didn't realize they were the nation's most famous college freshmen. 

"There's no guidebook," Jenna noted on Watch What Happens Live of attempting to navigate those early adult years as everyone watches. But her dad very much wanted that she and Barbara have the standard university experience even as he sat behind the most famous desk in the land. "His whole thing was like, 'Y'all can be normal college kids. You go be you,'" she said of the advice he gave as Barbara headed to his alma mater, Yale, and Jenna matriculated closer to home at the University of Texas. "And then he realized pretty soon after that that we really couldn't be normal college kids."

Shealah Craighead/The White House via WireImage

They made do, of course, bouncing back from that initial surge of headlines with a mix of humor (Jenna joking in their 2017 book Sisters First: Stories From Our Wild and Wonderful Life that she preferred the New York Post's coverage of the incident because they "used a much better photo" and "dubbed me the pithy 'Jenna and Tonic'") and enough good behavior that critics were able to realize that maybe two college kids drinking wasn't the earth-shattering news it was made out to be. 

Following their 2004 graduation, Jenna got a teaching job and became involved in UNICEF while Barbara—a memory of meeting a young AIDS patient fresh in her mind—traveled around Africa working with those struggling with the syndrome. Together they founded the New York-based nonprofit Global Health Corps.

Jamie Squire/Getty Images

But that feeling of living under a never-ceasing spotlight was fresh in their minds when Barack Obama was elected the United States' 44th president on Nov. 4, 2008. 

So less than a week later, as Jenna and Barbara detailed in a 2017 letter shared with TIME, they traveled from their respective jobs in Baltimore and New York, arriving in D.C. to greet Michelle and her daughters, who were gazing at their new pad with equal parts excitement and nervous anxiety. 

"The four of us wandered the majestic halls of the house you had no choice but to move in to," the twins wrote. "When you slid down the banister of the solarium, just as we had done as 8-year-olds and again as 20-year-olds chasing our youth, your joy and laughter were contagious."

Anything that wasn't covered that evening, Jenna and Barbara addressed months later in an open letter shared with The Wall Street Journal, highlighting their favorite play spaces (the curtains in the East Sitting Room creating the perfect spot to play house; the lawn ideal for an epic round of Sardines) and the opportunities they were grateful to experience. 

But the Bush twins' most pressing guidance involved tuning out as many of the critiques as they could, noting how upsetting it could feel each time their father was skewered by a late night comedian or mocked in a political cartoon. 

"Many people will think they know him, but they have no idea how he felt the day you were born, the pride he felt on your first day of school, or how much you both love being his daughters," they shared in their notes. "So here is our most important piece of advice: Remember who your dad really is."

As for any other attacks that may come Malia and Sasha's way, well, they had backup. Former first daughters Jenna, Barbara and Chelsea being well-versed in how painful a nation's worth of attacks can feel, they never hesitated to speak up. 

Not long after a GOP congressional aide scolded the teens for wearing too-short hemlines at the all-important turkey pardoning ceremony (the woman resigned after posting her quickly recanted Facebook missive instructing them to "Dress like you deserve respect, not a spot at a bar"), Jenna turned up on Watch What Happens Live in December 2014 in Malia and Sasha's defense.

"I'm fiercely protective of them, obviously," Jenna said. "I don't think that it's easy. It's not a job that they wanted."

But it is one that comes with perks. When nearly a year after Barack left office a video appeared to show Malia, then a freshman at Harvard, smoking, the whole first kids squad turned out, both Ivanka Trump and Chelsea tweeting statements more or less saying, Can a girl live? As Chelsea put it, "Malia Obama's private life, as a young woman, a college student, a private citizen, should not be your clickbait."

Because by then, of course, both she and her younger sister had officially left the White House behind, embarking on the next chapter of their lives that would see them figuring out who they were meant to be beyond the adorable family photos and well-known last names. 

"You are about to join another rarified club, one of the former First Children—a position you didn't seek and one with no guidelines," Jenna and Barbara wrote in their 2017 TIME missive, published as the Obamas were clearing out their White House digs, and shuffling across town to a new stately pad. "But you have so much to look forward to. You will be writing the story of your lives, beyond the shadow of your famous parents."

Barack and Michelle Obama's Sweetest Moments

As such, they continued, Malia and Sasha needn't worry about anyone who dare judge any perceived missteps, as their membership came with a handful of ride or dies who were ready to put any detractors in their place. 

"Enjoy college. As most of the world knows, we did," they quipped. "And you won't have the weight of the world on your young shoulders anymore. Explore your passions. Learn who you are. Make mistakes—you are allowed to. Continue to surround yourself with loyal friends who know you, adore you and will fiercely protect you. Those who judge you don't love you, and their voices shouldn't hold weight. Rather, it's your own hearts that matter."

Pete Souza / White House

For Michelle that sort of backup was invaluable as she and her husband attempted to guide their girls from adolescence to adulthood relatively unscathed. 

Stopping by Good Morning America as part of the 2018 press tour for her memoir Becoming, she offered a public thank you to Chelsea, Jenna and Barbara for the role they had played: "I love those girls," the former first lady gushed. "I will love them forever for what kind of support they provided my daughters. They always had their backs. Somebody went after them in the press, Jenna would get in there and say something. Chelsea would send a tweet out, and that made a big difference."

And now that Malia and Sasha have come out the other side ("Our children emerged intact and they are wonderful, kind, thoughtful, creative—and not entitled—young women," Barack recently told People), their first daughters squad is there for them in a different way.  

AbacaPress /

"We reach out to each other," Jenna said on September's Watch What Happens Live in September. "Chelsea and I see each other around—well, we used to. Now, I don't see anybody. But we used to see each other around New York City. And I reach out to the Obama girls and vice versa."

And you better believe Jenna is ready should anyone take issue with, say, Malia turning up in a pal's music video or Sasha becoming a bit of a viral TikTok sensation.

"Barbara and I always saw ourselves in them because when they went into the White House, they were the same age that we were when our grandpa was inaugurated," the Everything Beautiful in Its Time: Seasons of Love and Loss author shared during a September episode of Justin Sylvester's podcast Just the Sip. "When they were leaving, they were our age when my dad became president. They were in their teens; they were 18, 19 years old. And we knew what that was like too."

More than anything, Jenna continued, "We knew that you want to be yourself. You want to be able to have the room to make mistakes without being criticized for silly things. And they are exceptional girls—I mean, now they're women!"

Presidential Dogs and Other Pets at the White House

At 22 and 19, Malia and Sasha have escaped the gauntlet that is White House living and navigated the onset of their adult lives with grace, even if that means quarantining back at home with Mom and Dad because of the coronavirus pandemic. And should they ever need a pick-me-up, well, they know who to call. 

"You have lived through the unbelievable pressure," Jenna and Barbara wrote in that 2017 letter. "You have listened to harsh criticism of your parents by people who had never even met them. You stood by as your precious parents were reduced to headlines. Your parents, who put you first and who not only showed you but gave you the world. As always, they will be rooting for you as you begin your next chapter. And so will we."

Latest News