By Michele Willens

When most people think of Theodore (or Teddy or T.R.) Roosevelt, they likely think of a Rough Rider storming San Juan Hill during the Spanish-American War, a “Bull Moose” starting a third party in 1912, or a granite face alongside Lincoln, Washington, and Jefferson’s on Mount Rushmore. If they’re Upper West Siders, they may recall the equestrian statue of Roosevelt that, until two years ago, welcomed visitors to the American Museum of Natural History. 

Upper West Side newsman/writer Edward O’Keefe spent the last few years writing a new biography (published in May by Simon & Schuster) of the former New York governor and United States president. The angle: the women who surrounded, nurtured, and advised Roosevelt throughout his life. These include his largely misunderstood mother, a pair of adoring sisters, and two beloved wives: Alice Hathaway Lee, a wealthy Bostonian, and Edith Carow, a childhood sweetheart who finally landed him years later. 

This was not necessarily O’Keefe’s plan when he started “The Loves of Theodore Roosevelt: The Women Who Created a President.” Originally, he told me, “I was just going to write about Theodore Roosevelt’s time in the west. But I kept bumping into all these incredible women. His mother, Mittie, who had been written off as superfluous and inconsequential, was lively and intelligent and the source of T.R.’s personality, even though she receded somewhat and allowed her daughters to shine. Those daughters were Corrine (known as Conie), a quiet and devoted supporter, and Bamie, who had the most impact on her brother’s career. “Roosevelt’s own daughter, Alice Roosevelt Longworth, always said if Bamie had been a man, or lived in a different time, she would have been the president,” says O’Keefe. “Bamie was to T.R. what Bobby Kennedy was to JFK.”

One thing many do know about Roosevelt is that he endured the saddest day imaginable. That was on Feb 14, 1884, when both his wife, Alice, and his mother died. The New York Times described the heavy fog as  “suicidal,” when Theodore made the five-and-a-half-hour trip from Albany to where his family was gathered at 6 West 57th Street in New York City. “There is a curse on this house,” his brother Elliott said. “TR held Alice eleven hours before she died,” says O’Keefe, “essentially in childbirth. He cut some of Alice’s hair and kept it his whole life.”  Such deep-dive research makes Roosevelt more relatable. As historian Jon Meacham wrote, “This book reminds us that leaders are not made of marble but of heart and flesh.” 

Among the many things that may surprise you reading “The Loves of Theodore Roosevelt: The Women Who Created A President” is how enlightened this supposed bully was about feminist and racial issues. The subject of his college thesis in 1880 was why women should be allowed to vote — and even to refuse to change their names upon marriage. He spoke out against lynching, invited Booker T. Washington to the White House, and served on the board of Howard University. Not surprisingly, considering how much time he spent on “stolen” land, he visited reservations and named his own ranch Sagamore Hill, in honor of a native-American chief with that name. The last speech T.R. ever gave was at Carnegie Hall with civil rights activist W.E.B Du Bois. 

Which brings us to the statue that stood for so long just blocks from where O’Keefe lives. A Theodore Roosevelt Presidential Library is under construction in Medora, North Dakota, set to open in 2026. (O’Keefe is CEO of the Theodore Roosevelt Presidential Library Foundation.) The library took possession of the statue. (One criterion for its removal was that it have a destination.) There remain four quotes from Roosevelt inside the museum. And Robin Williams brought him to cinematic life in “Night At The Museum.” According to O’Keefe, “the sisters fought the statue, and Theodore, while he was alive, always said he did not want a statue of any kind depicting him.” 

Theodore Roosevelt was larger than life, with countless interests, from bird watching to taxidermy to, more importantly, social justice, equality, and trust busting. But in this book, as in life, the women around him flourished as well. Edith waited years watching her first boyfriend marry “up” to a Brahmin. “You could not have found two more different women, and he loved them both” says O’Keefe. “Bami was so ecstatic that Edie was back in their lives, but also knew what lay ahead. She told Edie, “You are going to have to share him with the world.’’ 

O’Keefe, who won Emmy Awards for his work at CNN and ABC, lives with his wife, Allison, and their two children in the Ardsley (where they watched through their window as Barbra Streisand’s piano was craned to the top). “I love the Upper West,” he says. “It feels like a neighborhood. Gennaro is our go-to place. I love Edgar’s [Cafe]. Ben, the owner, is a character. T.R., by the way, was a huge fan of Edgar Allen Poe. He constantly made references to his work, and took one of Poe’s books with him to the [South Dakota] Badlands. ‘They look the way Poe writes,’ Roosevelt noted.”

“And, of course,” O’Keefe adds, “I love our bookstores: Shakespeare and Co., Book Culture, Barnes and Noble, The Strand, and others — we’ve got them all.”  And all will soon have his new book in their front windows. 

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