She smoked cigarettes, raced automobiles, kept a pet snake named Emily Spinach, and delighted in scandalizing Washington society. Alice Roosevelt Longworth, the eldest child of President Theodore Roosevelt, was by nature rebellious. So much so that her father once admitted, “I can be President of the United States, or I can control Alice. I cannot possibly do both.”

Yet Alice would become one of Washington’s most enduring presences — a sharp-tongued observer who challenged status quos and delighted in saying, “If you haven’t got anything nice to say about anybody come sit next to me.”

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Alice was born on February 12, 1884, in a brownstone in New York City, into an orderly, loving, and prosperous household. Two days later, on Valentine’s Day, that household collapsed. Her mother, Alice Hathaway Lee Roosevelt, died around 2pm of what physicians would later understand to be undiagnosed kidney failure. That same afternoon, in an upstairs bedroom of the same house, Theodore’s mother, Martha “Mittie” Bulloch Roosevelt, died of typhoid fever.

Theodore was in Albany for work as a New York State Assembly member as the 12th approached, busy attempting to pass legislation he had proposed. He had written his wife earlier, “How I did hate to leave my bright, sunny little love yesterday afternoon! I love you and long for you all the time, and oh so tenderly; doubly tenderly now, my sweetest little wife. I just long for Friday evening when I shall be with you again.” Now, as a telegram arrived with news, he rushed home to find his wife and mother both in critical states.

Theodore would hold his wife in his arms for hours, as she lay dying, only to separate to see his mother one last time before she passed. That night, he drew a single black X atop the page of his diary, and wrote beneath it: “The light has gone out of my life.”

Grief overtook Theodore. A family friend described him as “in a dazed, stunned state. He does not know what he does or says.” Unable to care for Alice, he handed his infant daughter to his older sister, Anna Roosevelt Cowles, and left for the Dakota Territories to cope a few months later…

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