Raab’s Guest Curator Ed O’Keefe Annotates a Selection of Historical Documents and Sheds Light on the Life of President Theodore Roosevelt
Edward F. O’Keefe is CEO of the Theodore Roosevelt Presidential Library Foundation and author of the new book, The Loves of Theodore Roosevelt (Simon & Schuster, 2024). He previously spent two decades in broadcast and digital media at ABC News, CNN, and NowThis, 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’s 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.
Theodore Roosevelt Exhibit Curated by Edward O’Keefe
Though his exploits in Cuba made him a global celebrity, Theodore Roosevelt’s election as New York’s governor in 1898 was hardly assured. The Rough Rider reformer Republican won by less than 18,000 votes. The campaign was hard-fought. Democrats questioned his citizenship and legal right to run for governor since he paid taxes in Washington, D.C., not New York prior to his military service. I write in The Loves of Theodore Roosevelt about how TR’s younger sister countered the offensive by secretly giving her brother’s wartime letters to the press to “further fan the flames of her brother’s celebrity.” This remarkable document reminds us there is a thin line between victory and defeat. Had Theodore lost that very close election in 1898, his political career would have been over before it reignited. TR knew he owed his victory to more than just Republicans: “I shall strive to administer the office of the governor in the interests of the whole people. It is by so doing that I can best show my appreciation of the support given to me by the independents and Democrats….”
Theodore Roosevelt Selects His Campaign Manager For His 1904 Presidential Campaign
“The one great ambition of Theodore Roosevelt’s was to be chosen President on his own merits by the people of the United States,” wrote Theodore’s younger sister, Conie. In her always wise words, Theodore loathed the idea of coming to power “through a dead man’s shoes” upon the assassination of William McKinley. 1904 was Theodore’s chance to win the election outright. In The Loves of Theodore Roosevelt, I reveal how uncertain he was of his chances. “Whether I shall be re-elected I haven’t the slightest idea,” he wrote Conie. To his older sister and essential confidante Bamie, TR also wrote: “On election night Edith intends to have members of the Cabinet around. And we intend to have a little feast which can be turned into a festival of rejoicing or into a wake, as circumstances warrant!” This rare document takes history inside one of TR’s most consequential political decisions in 1904: the selection of his campaign manager. It was a good one. TR won in a landslide: 336 to 140 in the electoral college and well over 2.5 million in the popular vote.
Denied the Republican nomination he rightfully won, Theodore Roosevelt bolted the party and ran as the Progressive Party candidate in 1912. The Bull Moose was — and to this day is — the most successful third party independent candidate in U.S. presidential election history. Ahead of the ill-fated but historic race, I write in The Loves of Theodore Roosevelt about how Edith, TR’s beloved second wife, leveled him with a hard truth: “Put it out of your mind, Theodore. You will never be President of the United States again.” She was right (as she often was). The loss was devastating. TR wrote his autobiography, explored the River of Doubt, and tried, as evidenced in this letter, to keep his dimmed electoral prospects alive. He refused to stand as the Progressive Party nominee in 1916, and the Republican Party refused to have him back. By 1920, the year in which TR was favored once again as the Republican nominee, he would be dead long before Election Day.
The Last Days of Abraham Lincoln: Signed the Day He Made His Final Speech, 4. April 11th, 1865
Abraham Lincoln described the Declaration of Independence as an “apple of gold” in a “picture of silver.” He saw our Declaration, which will turn 250 years old alongside our country in 2026, as our mission statement and the Constitution as our governance. Many presidents subsequent to Lincoln have admired his leadership and wisdom — among them Theodore Roosevelt. In The Loves of Theodore Roosevelt, I reveal for the first time the existence of a letter dated December 31, 1861, the year that marked the beginning of the Civil War. The letter is from Theodore Roosevelt, Sr., to his three-year-old son, Theodore. In it, father tells son that he has just met with President Lincoln. ‘Thee’ encourages his son to learn by heart the words etched in the statue of Andrew Jackson in Lafayette Square: “The Federal Union, It Must be Preserved.” That is a letter as remarkable and chilling as this one. This letter is dated April 11th, 1865, just three days before Lincoln’s assassination on Good Friday. On April 26th, 1865, a mere fortnight and a day after Lincoln signed this letter, his body arrived in New York City en route to entombment in Springfield, Illinois. There was a little boy watching the funeral procession traverse up Broadway from his grandfather’s window: his name was Theodore Roosevelt.
This unusual book appealed to me as a historian and writer because of the surprising links between so many great entrepreneurs, naturalists, and politicians of the early twentieth century. I write in The Loves of Theodore Roosevelt that Thomas Edison said of TR in 1916 that he “is absolutely the only man that should be considered [for the presidency] at this crucial point.” Edison backed TR’s independent run in 1912 and used the emerging technology of the time — recorded sound — to help the candidate he backed. The history of Roosevelt and John Burroughs is more storied and well-known than the connection between America’s great inventor and TR. My favorite story of TR and Burroughs comes from their trip to Yellowstone in 1903. Believe it or not, the President and the naturalist went skiing. Burroughs wrote: “At the President’s suggestion, he and I raced on our skis down those inclines. We had only to stand up straight, and let gravity do the rest. As we were going swiftly down the side of one of the hills, I saw out of the corner of my eye the President taking a header into the snow … I kept straight on, and very soon the laugh was on me, for the treacherous snow sank beneath me, and I took a header, too.” When I saw this book — a commemoration of a road trip involving two inventors and a naturalist — it reminded me of this story which for me personalizes these distant figures. They were human — with foibles, a sense of humor, and adventure. What a profound way to remind us all that our heroes are made of flesh and blood. (For a bonus, please also see this wonderful letter from Theodore Roosevelt to John Burroughs which illustrates the longevity and closeness of their bond.)
In celebration of its 35th year as dealers of important historical documents and autographs, The Raab Collection is inviting prominent authors, historians, and thought leaders to participate in its Guest Curators program. To learn more, read our press announcement or visit our Guest Curators page.
