Honestly, if you think you know Eleanor Roosevelt from a high school history textbook, you’ve basically just seen the tip of a very massive, very complicated iceberg. Most people picture her as this grandmotherly figure in a pearls-and-polka-dots dress, the "First Lady of the World" who smiled nicely while her husband, FDR, ran the country.
That version is kinda boring. And it’s mostly wrong.
The real facts of Eleanor Roosevelt paint a picture of a woman who was essentially a political insurgent living inside the White House. She was a teacher who refused to stop working, a journalist who out-earned the President, and a woman whose personal life was way more "modern" than most people in the 1930s could have handled. She didn’t just support her husband; she often forced his hand on issues he’d rather have ignored.
The First Lady Who Made More Money Than the President
Here is a fact that usually catches people off guard: Eleanor Roosevelt was a financial powerhouse. Between 1932 and 1940, while the country was clawing its way out of the Great Depression, she was a one-woman media empire.
She wrote a daily newspaper column called "My Day" that ran for nearly thirty years. She did radio broadcasts. She gave paid lectures. In those eight years, she earned what would be roughly $12 to $14 million in today’s money.
- She earned twice as much as Franklin's official presidential salary.
- She didn’t hoard it; she gave almost all of it away to charities and New Deal causes.
- She used her own money to fund a private school for girls called the Todhunter School.
She wasn't just a "plus one." She was a professional. Even after FDR became Governor of New York, Eleanor kept commuting to New York City to teach history and literature several days a week. She refused to give up her identity just because her husband was climbing the political ladder.
Redefining the "First Lady" Role (by Breaking Every Rule)
Before Eleanor, the First Lady’s job was basically to host tea parties and not say anything controversial. Eleanor looked at that and said, "No thanks."
She started holding her own press conferences. But there was a catch—she only allowed female reporters to attend. This wasn't just a "girl power" move for the sake of it; it was a calculated strategy. By making her press conferences "women only," she forced newspapers to keep women on their payrolls. If a paper wanted the scoop on what was happening in the White House, they had to hire a female journalist.
She also became the "eyes and ears" for FDR. Because of his polio, he couldn't travel easily. So, Eleanor became his scout. She logged over 40,000 miles in just three months once. She’d go down into coal mines, visit tenements, and sit with sharecroppers. She would then come home and tell Franklin exactly how much his policies were—or weren't—working.
The Civil Rights Insurgent
One of the most defining facts of Eleanor Roosevelt is that she was lightyears ahead of her husband on racial justice. While FDR was often afraid to push for civil rights legislation because he didn't want to lose the support of Southern Democrats, Eleanor didn't care about the politics of it. She cared about the ethics.
In 1939, the Daughters of the American Revolution (DAR) refused to let Black singer Marian Anderson perform at Constitution Hall. Eleanor didn't just send a polite letter of protest. She resigned from the organization entirely and made sure everyone knew why. She helped arrange for Anderson to sing at the Lincoln Memorial instead, which turned into a massive event for 75,000 people.
Then there was the 1938 Southern Conference for Human Welfare in Alabama. The authorities tried to force the crowd to sit in segregated sections. Eleanor took her folding chair and placed it right in the middle of the aisle—the literal dividing line—as a "middle finger" to the segregation laws.
The Tuskegee Airmen Flight
In 1941, people still widely believed that Black men didn't have the "natural ability" to fly planes. Eleanor went to the Tuskegee Army Air Field and asked the chief flight instructor, Charles "Chief" Anderson, to take her up. Her Secret Service agents were terrified, but she spent an hour flying over Alabama with a Black pilot. The photo of that flight went viral (well, the 1940s version of viral) and basically shamed the military into moving forward with the Tuskegee Airmen program.
The "Hick" Letters and a Private World
The most debated aspect of her life is her relationship with journalist Lorena Hickok, known to Eleanor as "Hick."
When you look at the archives, there are over 3,300 letters between them. Some of them are... intense. Eleanor wrote things like, "I want to put my arms around you in reality instead of in spirit," and "I went and kissed your photograph instead and tears were in my eyes."
Historians are split on whether the relationship was physical, but honestly, trying to put a modern label like "lesbian" or "bisexual" on it might be missing the point. Eleanor lived in a "lavender" world where her marriage was a political and intellectual partnership, but her emotional intimacy often lived elsewhere. Her marriage survived FDR's affairs (specifically with Lucy Mercer), but the couple reached a sort of "separate but equal" arrangement that allowed Eleanor to find love and support in her own way.
Her "Greatest Achievement" Wasn't the White House
If you asked Eleanor what she was most proud of, she wouldn't say being First Lady. She’d point to her work at the United Nations after Franklin died.
President Truman called her the "First Lady of the World" and appointed her as a delegate to the UN. She was elected chair of the Human Rights Commission, where she spent two years—and over 3,000 hours of deliberations—drafting the Universal Declaration of Human Rights (UDHR).
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Imagine trying to get the US, the Soviet Union, and 50 other countries to agree on what "human rights" even are during the start of the Cold War. It was a nightmare. But she did it. She pushed through 30 articles that defined basic dignity for every human being on Earth. She considered this her legacy.
A Summary of Surprising Realities
To make these facts of Eleanor Roosevelt easy to digest, let's look at the stuff that usually stays out of the mainstream narrative:
- FBI Target: J. Edgar Hoover hated her. He kept a massive file on her because of her civil rights work and her associations with "radical" youth groups. He basically thought she was a security risk.
- The Gun-Toting First Lady: She actually had a permit to carry a pistol. She often drove herself around without a Secret Service detail, and she kept a .22 Smith & Wesson for protection.
- A "Failure" in West Virginia: She tried to build a homestead community called Arthurdale for destitute mining families. It was an experimental town meant to prove that government could provide a "new deal" for the poor. It was expensive and mostly flopped, which her critics never let her forget.
- The Christmas Shopper: She started her Christmas shopping on December 26th every year and shopped year-round. It was her way of feeling connected to people; she felt she had to "earn" love through acts of service and gifts.
Actionable Insights: Learning from Eleanor
Eleanor Roosevelt wasn't born a bold leader. She was a shy, orphaned girl who felt "ugly" and "unloved" for most of her youth. Her transformation is a blueprint for anyone trying to make an impact.
- Use Your Privilege to Open Doors: Eleanor didn't just talk about women’s rights; she created a "women-only" rule at her press conferences to force the industry to change. Look for ways to use your current platform to mandate inclusion.
- Be the "Eyes and Ears": Don't rely on reports or second-hand data. Eleanor went into the coal mines. If you're a leader, go to the "front lines" of your project or community to see the reality for yourself.
- Separate Personal Grief from Public Purpose: Despite a heartbreaking marriage and constant public scrutiny, she channeled her need for love into a global fight for human rights.
- Write Your Own Story: She didn't let the White House define her. She wrote her own columns, taught her own classes, and earned her own money.
If you want to dive deeper into the real Eleanor, I highly recommend reading The Defining Years by Blanche Wiesen Cook. It gets past the "polite" history and into the grit of her political battles. You can also visit the FDR Presidential Library website to read some of the 3,000+ letters between Eleanor and Hickok to see the human side of the icon.
Start by picking one cause you care about and, like Eleanor, find a way to "sit in the aisle" when everyone else is telling you to pick a side.