President Franklin D. Roosevelt talks to his daughter Anna on board the USS Quincy before meeting with Winston Churchill and Joseph Stalin at Yalta. (The FDR Presidential Library)

Ivanka Trump is the first first daughter in American history to score a West Wing office and hire a chief of staff. As her father’s “special adviser,” her portfolio encompasses both outreach to Europe and rolling her eyes at commander-in-chief dad jokes. In Berlin on Tuesday, she endured boos when she called the president a “champion” for families during a panel discussion with German Chancellor Angela Merkel, International Monetary Fund Managing Director Christine Lagarde and other female leaders

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But Ivanka is far from the first adult daughter to leave a mark on White House history. The teen rebel Alice Roosevelt, for example, may have scorched some marks on the White House roof, given her habit of sneaking cigarettes up there in defiance of father Teddy Roosevelt’s no-women-smoking rule. “I can either run the country or I can attend to Alice, but I can’t possibly do both,” a frustrated T.R. once famously declared.

But after maturing a bit, Alice’s had real impact as a glamorous fashion plate who was dispatched to represent her father on a diplomatic tour of five Asian countries in 1905, even as the president was helping to mediate peace between Japan and Russia.

“He harnessed her spunk, and she became a political asset,” said Joshua Kendall, author of “First Dads,” a book on presidential parenting. “She was very stylish the way Ivanka is, although she wasn’t selling her handbags.”

Alice Roosevelt in 1902. (Frances Benjamin Johnston Collection/ Library of Congress)

Alice did sell cigarettes, though, long after she set up her Georgetown salon and was widowed from her husband, House Speaker Nicholas Longworth. She flogged Lucky Strikes in print ads, quipped like Dorothy Parker and was a legendarily acerbic hostess in Washington society into her 90s.

But the time wasn’t right for her to play more of an overt policy role in her father’s administration. “She was extremely intelligent,” said her biographer, Iowa State University history professor Stacy Cordery. “People always said if she had been a boy she would have been president.”

Cordery says nothing in first family history compares to the reach and depth of Ivanka Trump’s official role. But her own vote for most influential first daughter in the pre-Ivanka age may go to Maureen Reagan, the Gipper’s child with actress Jane Wyman.

Maureen — Mermie, as her dad called her — lived at the White House during much of her dad’s presidency, where she was a reportedly a voice of moderation on women’s issues whispering in his ear. (Sound familiar?) She was active in party politics, co-chairing the Republican National Committee and running

None Former first lady Nancy Reagan, left, receives a hug from her stepdaughter Maureen Reagan at the 2000 GOP convention. (Hillery Garrison Smith/AP)

unsuccessfully for public office twice in California before dying of cancer in 2001.

Like Alice Roosevelt, Maureen’s half-sister Patti Davis thrived in the wild-child category of first daughters. She posed topless in the July 1994 issue of Playboy, five years after her father left office. Ivanka hasn’t done that, though first lady Melania Trump posed in the buff on a fur blanket handcuffed to a leather briefcase aboard Trump’s jet in 2000.

Anna Roosevelt played a less flamboyant but more central role in her father’s White House. FDR turned to his daughter as an all-around helpmeet when his relationship with Eleanor Roosevelt had become strained and distant.

Anna was working as a journalist on the West Coast when Roosevelt asked her to come back to Washington during World War II. She ran his social calendar, took a hand in managing access to him and is credited by some with persuading him to pick Harry Truman as his final running mate. Life magazine took note of her influence by suggesting, “Daddy’s girl is running Daddy.”

It was Anna the president asked to accompany him to meet Winston Churchill and Joseph Stalin at Yalta.

“He seemed more comfortable with his daughter for things like this,” Kendall said. “Yes, like Trump.”

Martha “Patsy” Jefferson Randolph took up first lady duties during two winters at the White House for her widower father, Thomas Jefferson. In 1806, she gave birth to the first baby born at the White House.

First daughter Margaret Truman made a name for herself as an enthusiastic, if not accomplished, singer. When Washington Post critic Paul Hume panned her 1950 performance at Constitution Hall, her father let him have it in a note written on White House stationery.

“Some day I hope to meet you,” President Harry Truman wrote. “When that happens you’ll need a new nose, a lot of beefsteak for black eyes, and perhaps a supporter below!”

Margaret Wilson was also a singer, but a less notorious one. She took over first lady duties when Woodrow Wilson’s first wife died. Wilson had three daughters, who reportedly lobbied him to back the women’s vote and support the 19th Amendment.

None President Trump and daughter Ivanka Trump walk to Marine One in February. (Evan Vucci/AP)

His youngest, Ellen Wilson, married Wilson’s treasury secretary at the White House, making William McAdoo arguably the most powerful presidential son-in-law in history.

On whether that achievement will survive in the age of Jared Kushner, Ivanka’s influential husband, history is still out.

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