Daughters of an American Revolution

Donald Trump and Hillary Clinton may be on opposite sides of the political spectrum, but they have one thing in common: media-savvy daughters who are instrumental to their campaigns.

Indeed, Chelsea Clinton and Ivanka Trump have arguably been as integral to their parent's presidential bid as any adviser, humanizing their polarizing progenitors after gaffes on the trail and generally being a calming presence in Hillary's and Donald's soap-operatic lives.

It's no wonder that Chelsea, 36, and Ivanka, 34, (Chevanka?) gravitated toward each other in recent years, complimenting each other on Twitter and in the pages of Vogue. Fledgling friends before the campaign, they were often spotted together at A-list events, meticulously tousled hair tumbling past their shoulders, teeth as dazzling as the camera lights chronicling their every step.

It made perfect sense: Their parents were once friendly as well, before becoming political rivals. The Clintons attended Donald Trump's 2006 wedding to Melania Knauss, and Ivanka and her father donated money to Hillary Clinton's 2008 presidential bid. (Donald Trump was a supporter of Democrats before he became, well, less so.)

It's not just that Chelsea and Ivanka ran in the same red carpet circles; who else could a young heiress of financial or political capital turn to but someone cut from the same cloth?

For high-profile women like these two, "it's hard to know whether others are interested in you, or whether they just want to meet your parents and bask in fame by association," says Jane Greer, a psychotherapist and celebrity commentator. "It's hard to trust people and know when they're being authentic and genuine."

The Daughters have other striking similarities: Both share the unique humiliation of learning more about their father's sexual proclivities than a child should ever know. Both endured relentless commentary about their physical appearances as young women—sometimes vicious in Chelsea's case, as she spent her awkward years in the White House, and glowing (if not lascivious) in the case of Ivanka, a onetime model.

Today, the two are poised, articulate, and well-educated professional women, each of whom also happened to marry a Jewish man whose father has done time in jail for white-collar crimes. (Ivanka also converted to Judaism.) And despite being mothers to toddlers, both have remained visible surrogates for their parents throughout the campaign.

After stints as a management consultant at McKinsey & Company, a financial analyst, and an occasional "special correspondent" at NBC (for a widely ridiculed $600,000 a year), Chelsea Clinton is now vice chair of the Clinton Foundation. She takes no salary for her work there, but earns six figures from her speaking engagements, which she says she funnels back into the foundation. On the trail, she emphasizes her role as a working mother: "I stand here first and foremost now as a mom myself," she told New Hampshire voters before that critical primary. More than the candidate's daughter, she is the mother of the candidate's granddaughter—and few things soften a politician's rough edges more than images of her as a doting grandma.

As for Ivanka, in addition to being executive vice president of development and acquisitions for the Trump Organization, she also markets lines of clothing, shoes, fragrance, and accessories and runs an eponymous lifestyle site, which trumpets itself as "The ultimate destination for #WomenWhoWork." (It's arguably a more empowering message than her mother Ivana's famous dictum, shared after her 1992 divorce from Donald: "Don't get mad. Get everything!")

The Daughters do differ in their approach to their private life. Chelsea has released only one photo of her daughter, Charlotte, to her 1.07 million Twitter followers—and that was when she announced that she was pregnant with her second child. She is far more public about her politics and wrote a book, It's Your World, meant to encourage 10- to 14-year-olds to make a difference.

Ivanka, who once routinely appeared with her father on his NBC reality show, The Apprentice, often tweets photos of her children to her 1.86 million followers, but rarely posts about policy specifics. Not to say that she doesn't have solid political instincts: She may have failed to register as a Republican in New York in time to vote for Donald Trump—a mistake one senses Chelsea Clinton would never make—but she did formally introduce her father to the public when he announced his candidacy. And when he lambasted China for its trade policies, Ivanka played good cop, posting to Instagram a video of her 4-year-old daughter singing a Chinese New Year song in Mandarin. No neophyte, she wrote in her 2010 book, The Trump Card: Playing to Win in Work and Life, "We Trumps don't play to perception. We play to win."

A Childhood As Buffers

Chelsea Clinton was a 17-year-old Stanford freshman when the Monica Lewinsky scandal broke in January 1998. Just a few years younger than the White House intern at the time, Chelsea has never spoken publicly about the incident. Confronted about it by an attendee at a 2008 speech at Butler University in Indiana, she responded: "Wow, you're the first person actually that's ever asked me that question in the, I don't know, maybe 70 college campuses I've now been to, and I do not think that is any of your business."

Ivanka was eight when she learned of her father's affair with Marla Maples, who had giddily informed the public how fabulous Donald Trump was in bed. Like Chelsea, Ivanka has never talked about the impact that time had on her. But in a 1990 Vanity Fair feature, Ivana Trump addressed how traumatic the divorce was for the couple's children. "Ivanka now comes home from school crying, 'Mommy, does it mean I'm not going to be Ivanka Trump anymore?' Little Eric asks me, 'Is it true you are going away and not coming back?'" Ivanka went to boarding school at Choate Rosemary Hall, but remained exceptionally close to her father, and today, by all accounts, wields an enormous amount of clout in his company.

Since neither of the daughters openly discusses the impact her father's scandals have had on her, others can only speculate. But it can't have felt good for Chelsea to have come across the widely disseminated Starr Report, which described the president's sexual escapades down to details like a penile birthmark. In her book, Living History, Hillary Clinton wrote that Chelsea was "confused and hurt" after the scandal and avoided her father for a while.

And yet it also must have been a little odd for Ivanka to hear her father comment on her physical attributes, as he once did in a Rolling Stone interview: "Yeah, she's really something, and what a beauty, that one. If I weren't happily married and, ya know, her father…"

"I like to think they each have an eyebrow raised at their dad," says Rachel Kitson, a psychologist in Charlotte, North Carolina, who often writes about issues in pop culture. "They're defensive of their dad and seem to have healthy relationships with their parents, but I also think they're kind of skeptical and jaded, especially about their father's antics. I imagine they keep those thoughts and feelings pretty private, and they're selective about whom they keep in their inner circle."

What might Chelsea and Ivanka have done with those feelings? Jeanne Safer, a psychoanalyst and the author of The Golden Condom, points to the possibility of reaction formation—the avoidance of uncomfortable feelings by adopting the opposite position. "Chelsea had to do something with her feeling that there was something morally wrong with her father," she says.

"When this happens to a young woman, that kind of betrayal—I think Chelsea denied the whole thing and took her mother's point of view, that [Clinton's impeachment] was a 'vast right-wing conspiracy.' Instead of thinking, My father acted horribly, you think, The world is against my parents. Chelsea aligned herself with both her parents. She took the line they both took."

In her book The Residence: Life in the White House, Kate Andersen Brower interviewed the children of four former presidents, including Gerald Ford's son, Steve, who recalled writing a note to Chelsea Clinton in 1992 advising her to befriend the Secret Service agents assigned to her. "They become your lifeline," Brower said. "Ron Reagan and Luci Baines Johnson also said they felt bad for Chelsea for being an only child in the White House."

Never was that role in starker relief than in the famous 1998 photo of the three Clintons walking hand-in-hand-in-hand on the South Lawn soon after the Lewinsky scandal broke. The body language is wrenching: Bill's head is bent forward, as if in prayer, clasping the family dog's leash. You can practically see Hillary's rage churning beneath her sunglasses. And Chelsea is, quite literally, the buffer between them, though her body is angled toward her mother.

The Family Trade

That Chelsea and Ivanka each signed up to work with her parent, despite all the accumulated baggage of decades in the public eye, doesn't surprise many observers of political families. "As they each got older, and got more organic exposure to the fields of their parents, they found they couldn't resist what was in their blood or drive," says David Greenberg, a professor of history at Rutgers and the author of Republic of Spin. "It's what they know."

Certainly, there may be more than a bit of self-interest at play. But Safer wonders if there's not a subconscious impulse, too. "It's a way to hold on to their parents and be part of them and deny that anything bad happened," she says. It's also a signal of forgiveness: What better tribute can a child give to a parent than to stump for him or her?

Ivanka Trump has vehemently defended her father after his most inelegant comments. When he made disparaging remarks about Carly Fiorina's appearance, Ivanka insisted in an interview with Town & Country that he is "one of the great advocates for women, and he has been a great example to me my whole life."

Trump's and Clinton's fathers aren't the only challenging men in their lives. Charles Kushner, father of Ivanka's husband, Jared, is a real estate developer and onetime Democratic political fundraiser in New Jersey who spent a year in federal prison for tax evasion and making illegal campaign contributions. Ed Mezvinsky, father of Chelsea's husband, Marc, is a former Democratic congressman from Iowa who served five years in federal prison for bilking investors, including family and friends, out of more than $10 million through get-rich-quick schemes.

"Maybe the reason Chelsea and Ivanka each relate to their spouse is because they also have a father who maybe let them down and lived bigger than he could," Kitson says. "They can confide in each other and form a bond that way."

Whichever daughter is on the winning side in November, she will face a new level of attention, perhaps unprecedented for a First Child of any age. While all evidence suggests that both Chelsea and Ivanka are up to the task, says Suniya Luthar, a psychology professor at Arizona State University who has studied the challenges facing children of great wealth, "even with people who seem OK, every one of us has baggage. The issue really is to what degree we carry it around. I hope for their sakes that they have it together."

Daughter vs. Daughter

Chelsea Clinton

Age: 36
Education: B.A. from Stanford, M.P.H. from Columbia, M.Phil. and doctorate in International Relations from Oxford
Children: Charlotte and Aidan
Value of Manhattan Apartment: $10.5 million
Treasured Possession: Her grandmother Dorothy Rodham's jewelry
Favorite Childhood Book: A Wrinkle in Time by Madeleine L'Engle
You did not know she... Gave up meat for 18 years, but has gone back.
Philosophy: "Life is not about what happens to you, but what you do with what happens to you."

Ivanka Trump

Age: 34
Education: B.S. from the Wharton School of Business at Penn
Children: Arabella, Joseph, and Theodore
Value of Manhattan Apartment: $16 million
Treasured Possession: Flowers she collected, dried, and made into paperweights
Favorite Childhood Book: The Giving Tree by Shel Silverstein
You did not know she... Records all the Real Housewives series on her DVR.
Philosophy: "People who are passionate always work the hardest, and
that sets them apart."

Facebook images: Albert H. Teich/Shutterstock; mistydawnphoto/Shutterstock