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Donald Trump's East Wing demolition trashes First Lady Eleanor Roosevelt's queer legacy

East Wing White House Eleanor Roosevelt at the United Nations
BRENDAN SMIALOWSKI/AFP via Getty Images; Public Domain via FDR Presidential Library & Museum

Heavy machinery tears down a section of the East Wing of the White House for U.S. President Donald Trump's planned ballroom, in Washington, D.C., on October 22, 2025; Eleanor Roosevelt at the United Nations.

Eleanor Roosevelt, who was likely queer, held the first press conference by a first lady in the East Wing, and the wing became a base for her activism.

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In demolishing the East Wing of the White House, Donald Trump is also demolishing part of the legacy of one of America’s greatest first ladies — one who was most likely a lover of women and definitely an advocate for them and other marginalized people.

Eleanor Roosevelt, President Franklin Delano Roosevelt’s wife, played a more public role than previous first ladies, and much of her work took place in the East Wing. The wing was constructed in the early 20th century under President Theodore Roosevelt — FDR’s distant cousin and Eleanor’s uncle — and significantly expanded during FDR’s presidency, which spanned 1933 to 1945.

The first press conference by a first lady

On March 6, 1933, two days after her husband’s inauguration, Eleanor Roosevelt held a press conference in the East Wing. She decided to hold the event, the first press conference by a first lady, at the suggestion of journalist Lorena Hickok, her great friend and probably her lover.

The press conference was groundbreaking in other ways as well. All 30 reporters attending it were women — Roosevelt had insisted that only women could cover her event. “At the time women made up a very small proportion of working journalists, but news agencies had to hire women if they wanted to cover ER,” according to an article posted by the Eleanor Roosevelt Papers Project at George Washington University.

She “sought to make women a part of the national political audience and inspired many women to stay informed and get involved,” the article continues. Roosevelt later wrote that she believed female journalists would report information “of special interest and value to the women of the country.” Of course, many men were interested in what she had to say too, on topics “such as the rising threat of Hitler in Europe or the challenges of social welfare institutions,” the GWU post notes. She would go on to hold nearly 350 press conferences during her time as first lady.

The office of the first lady and the East Wing

With a more public role for first ladies, they needed an office. Roosevelt employed the first social secretary for a first lady, and her secretary was stationed in the East Wing. “Roosevelt used the East Wing for official functions, as a base of operations for her activism and as a space for interacting with groups representing the American people, from the Girl Scouts to the Women’s Trade Union League,” The 19th reports.

Related: 20 Game-Changing Queer Women to Celebrate Women's History Month

The wing “evolved into the space where first ladies maintained offices,” Military Times notes, beginning with Rosalynn Carter; previously, some first ladies had offices in their bedrooms. Still, the East Wing had already seen much activity involving first ladies, even post-Roosevelt. Civil rights advocates marched outside the wing in the 1960s to get Lady Bird Johnson’s attention, and in the 1970s, “Betty Ford argued to increase pay for her staff in the East Wing,” as reported by The 19th. Laura Bush started her literacy campaign there, as Michelle Obama did with her “Let’s Move!” public health initiative.

Much “serious work” happened in the East Wing, but with Trump’s plans for a gilded ballroom costing $300 million, it won’t happen anymore, historian Alexis Coe told The 19th.Another historian, Katherine A.S. Sibley, told the site, “To me, this demolition suggests that the current White House does not think that the first lady does anything of value,” Sibley said. “I’m not talking about [Melania Trump] particularly, but the office itself — they’re not cognizant of the history.”

“Betty Ford had the best quote for how special the East Wing is: ‘If the West Wing is the mind of the nation, then the East Wing is the heart,’" Anita McBride, who was Laura Bush's chief of staff, recently told East Wing Magazine. “The walls may be gone, but those East Wing stories must be preserved and shared for future generations.”

Eleanor and "Hick"

It’s well documented that Roosevelt and Lorena Hickok were close, but there are things we can’t know. And there are those who clutch their pearls at the suggestion that a revered first lady could have been lesbian or bisexual — not in our community, of course. Here’s what we do know about the women and their relationship.

Hickok was already a successful journalist when she met Roosevelt in 1932, After escaping an abusive home, working as a maid, and flunking out of college, Hickok started her career with a small-town newspaper, then moved on to bigger papers in Milwaukee, New York City, and Minneapolis. She fought to get out of the society section and cover hard news, which she eventually did. She joined the Associated Press in 1928. She gained fame by covering the kidnapping of Charles Lindbergh’s infant son and other major stories.

In 1932, she was assigned to cover Eleanor during FDR’s presidential campaign. The two women became so close that in 1933, Hickok quit the AP because she felt she could no longer be objective about the Roosevelts. After FDR became president, Hickok went to work for the federal government, traveling to communities around the nation so she could research and report on the conditions in which Americans lived during the Great Depression. In 1940, she became executive secretary of the Democratic National Committee and moved into the White House at the first lady's invitation.

Related: 17 Iconic Same-Sex Couples Throughout History

Hickok influenced Eleanor Roosevelt’s political work; she encouraged the first lady to address the working and living conditions of coal miners and to begin writing a syndicated newspaper column, “My Day,” which Hickok edited. Some historians characterize the women as devoted friends, but others say unequivocally that they were in love. “I think that Hick was in love with Eleanor, and Eleanor was in love with Hick,” said Blanche Wiesen Cook, author of a three-volume biography, Eleanor Roosevelt, in a 1999 PBS interview. As to whether the relationship was sexual, Cook said, “Well, the fact is, we can never know what people do in the privacy of their own rooms. … But there’s no doubt in my mind that they loved each other, and this was an ardent, loving relationship between two adult women.”

As in any relationship, there were some tensions, as Hickok had essentially given up her career for love. But the women remained close for the rest of their lives, with Hick living near Eleanor in Hyde Park, New York. They collaborated on a book about women in politics, Women of Courage, and Hickok wrote a biography of Eleanor. The former first lady died in 1962 after a post-White House career that included being the first chairperson of the United Nations Commission on Human Rights and helping to draft its Universal Declaration of Human Rights. Hickok died in 1968, having worked for the New York State Democratic Committee after leaving the DNC.

There’s much information on their relationship in Cook’s biography, especially the second and third volumes. Also, about 300 of their letters are collected and annotated in Empty Without You: The Intimate Letters of Eleanor Roosevelt and Lorena Hickok, edited by Rodger Streitmatter. Their relationship has been fictionalized in the novel White Houses by Amy Bloom, which came out in 2018, and in the 2022 Showtime miniseries The First Lady, in which Gillian Anderson played Eleanor and Lily Rabe played Hick.

Their story will outlast the East Wing as well.

Related: Illinois Army captain says Dems are ‘rolling over’ on LGBTQ+ rights. He’s running for Congress to change that

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Trudy Ring

Trudy Ring is The Advocate’s senior politics editor and copy chief. She has been a reporter and editor for daily newspapers and LGBTQ+ weeklies/monthlies, trade magazines, and reference books. She is a political junkie who thinks even the wonkiest details are fascinating, and she always loves to see political candidates who are groundbreaking in some way. She enjoys writing about other topics as well, including religion (she’s interested in what people believe and why), literature, theater, and film. Trudy is a proud “old movie weirdo” and loves the Hollywood films of the 1930s and ’40s above all others. Other interests include classic rock music (Bruce Springsteen rules!) and history. Oh, and she was a Jeopardy! contestant back in 1998 and won two games. Not up there with Amy Schneider, but Trudy still takes pride in this achievement.
Trudy Ring is The Advocate’s senior politics editor and copy chief. She has been a reporter and editor for daily newspapers and LGBTQ+ weeklies/monthlies, trade magazines, and reference books. She is a political junkie who thinks even the wonkiest details are fascinating, and she always loves to see political candidates who are groundbreaking in some way. She enjoys writing about other topics as well, including religion (she’s interested in what people believe and why), literature, theater, and film. Trudy is a proud “old movie weirdo” and loves the Hollywood films of the 1930s and ’40s above all others. Other interests include classic rock music (Bruce Springsteen rules!) and history. Oh, and she was a Jeopardy! contestant back in 1998 and won two games. Not up there with Amy Schneider, but Trudy still takes pride in this achievement.