The Literary Cocktail Hour is an fun, informal monthly event featuring a pair (or more) of speakers in an entertaining, illuminating virtual event based on the notion of a cocktail hour.
The Loves of Theodore Roosevelt
Edward O’Keefe
with Michael Cullinane
Friday, May 17 at 5:00 pm
Online and free!
register at
On Friday, May 17, the Brattleboro Literary Festival will present Edward O’Keefe, author of The Loves of Theodore Roosevelt: The Women Who Created a President in conversation with historian Michael Cullinane.
Theodore Roosevelt wrote in his senior thesis for Harvard in 1880 that women ought to be paid equal to men and have the option of keeping their maiden names upon marriage. It’s little surprise he’d be a feminist, given the women he grew up with.
His mother, Martha “Mittie”, was witty and decisive, a Southern belle raising four young children in New York while her husband spent long stretches away with the Union Army. Theodore’s college sweetheart and first wife, Alice–so vivacious she was known as Sunshine–steered her beau away from science (he’d roam campus with taxidermy specimen in his pockets) and towards politics. His older sister Anna “Bamie” would soon become her brother’s key political strategist and advisor; journalists called her Washington, DC, home “the little White House.” His younger sister Corrine “Conie” served as her brother’s press secretary before the role existed, slipping stories of his heroics in Cuba and his rambunctious home life to reporters to create the legend of the Rough Rider we remember today. And Edith–Theodore’s childhood playmate and second wife–would elevate the role of presidential spouse to an American institution, curating both the White House and her husband’s legacy. A dazzling and lyrical look at one America’s most significant presidents as we’ve never seen him before, The Loves of Theodore Roosevelt celebrates five extraordinary yet unsung women who opened the door to the American Century and pushed Theodore Roosevelt through it.
Theodore Roosevelt in Vermont
Theodore Roosevelt was the 26th President of the United States(1901-1909). He was Vice-President when President McKinley was assassinated and was actually in Vermont when he was notified of the shooting. With the McKinley’s death, Roosevelt, not quite 43, became the youngest President in the Nation’s history. He brought new excitement and power to the Presidency, as he vigorously led Congress and the American public toward progressive reforms and a strong foreign policy. In 1902, while visiting a friend in Newfane, he made an appearance in Brattleboro. Theodore Roosevelt was married twice(his first wife died at age 22), and he was the father of six children. Sarah Alden Derby was the daughter of one of his children, Ethel Roosevelt. Sarah went on to marry Vermont State Senator Robert Gannet and they resided in Brattleboro.
Brattleboro 1901
Edward F. O’Keefe is the CEO of the Theodore Roosevelt Presidential Library Foundation. He previously spent two decades in broadcast and digital media, during which time he received a Primetime Emmy Award for his work with Anthony Bourdain, two Webby Awards, the Edward R. Murrow Award, and a George Foster Peabody Award for ABC News coverage of 9/11. A former fellow at the Harvard Kennedy School, he graduated with honors from Georgetown University. He was born in North Dakota and lives in New York with his wife, daughter, and son.
Michael Cullinane is a historian of American politics, an award-winning author, and the Lowman Walton Chair of Theodore Roosevelt Studies at Dickinson State University. He also serves as a Public Historian for the Theodore Roosevelt Association and contributes to the design and curation of the Theodore Roosevelt Presidential Library due to open in 2026. He is author of several books and hosts the popular podcast “The Gilded Age and Progressive Era.”
