Valentine's Day 1884—The Worst Day of Theodore Roosevelt's Life

A Dual Tragedy Struck Theodore Roosevelt on February 14, 1884. It Was the Crucible of Grief That Forged the Man Who Would Become President

On February 14, 1884, Theodore Roosevelt suffered an unimaginable tragedy—losing both his wife and mother on the same day, in the same house.

Just two days earlier, his wife, Alice Hathaway Lee Roosevelt, had given birth to their daughter. Roosevelt, who was at that time a young state assemblyman serving in Albany, was urgently called home to New York City because his mother, Mittie, had fallen gravely ill with typhoid fever.

By the time he arrived, however, he was met at the door by his brother, Elliott, who greeted him by saying: “There is a curse on this house.”

Upstairs, Alice—just 22 years old—was dying from undiagnosed Bright’s disease (a form of kidney failure, masked by pregnancy). Downstairs, his mother, just shy of 50, was slipping away due to typhoid fever.

At 3:00 AM, Mittie passed away. Hours later, Alice was gone too.

That night, Roosevelt opened his ever-present diary and, below a simple “X,” wrote:

“The light has gone out of my life.”

Alice had been the love of his life. Since meeting her in 1878, he had filled pages of his diary with details of their romance—her smiles, her laughter, the quiet moments they shared. But after that devastating day, he never spoke her name again. Not even to their daughter, Alice Longworth Roosevelt, who grew up never hearing her father utter her mother’s name.

Years later, he shared his philosophy on the pain of loss to a grieving friend: "The pain must be buried deep inside, or it will destroy you."

In a private tribute to Alice, Roosevelt wrote:

She was beautiful in face and form, and lovelier still in spirit; As a flower she grew, and as a fair young flower she died.

Her life had been always in the sunshine; there had never come to her a single sorrow; and none ever knew her who did not love and revere her for the bright, sunny temper and her saintly unselfishness.

Fair, pure, and joyous as a maiden; loving, tender, and happy as a young wife. When she had just become a mother, when her life seemed to be just begun, and when the years seemed so bright before her—then, by a strange and terrible fate, death came to her. And when my heart’s dearest died, the light went from my life forever.

Roosevelt reacted to the moment by abandoning his political career, withdrawing from New York politics, fleeing west to the Badlands of North Dakota, establishing himself at the Maltese Cross Ranch in Medora, North Dakota, and reinventing himself as a western man—a cowboy. But from the depths of his sorrow, he eventually rose again—returning to politics, becoming a war hero, and ultimately ascending to the presidency.

History remembers Roosevelt as a Rough Rider, a trust-buster, a conservationist, and a force of nature. But behind the legend was a man who once lost everything in a single day.