Born on November 25, 1960, in Washington D.C., John F. Kennedy Jr. would become the first infant to call the White House his home and was affectionately photographed with his big sister, Caroline, playing with their mother and father within the hallowed halls of 1600 Pennsylvania Ave.

But long before he grew up to be New York City’s most coveted bachelor of the ’80s and ’90s, Kennedy was deeply embedded into America’s historical fabric through tragedy when his father was assassinated on November 22, 1963. Three days later, on his third birthday, the image of the peacoat-clad Kennedy saluting his father’s casket would be one of the most heart-wrenching images of the ill-fated saga.

Three decades later on the evening of July 16, 1999, he would meet his own tragic demise when he accidentally flew his plane into the dark waters of the Atlantic Ocean off the coast of Martha’s Vineyard, Massachusetts, bound for a cousin’s wedding. Flying with him was his wife, Carolyn Bessette, and her older sister, Lauren Bessette. No one survived. Kennedy was only 38.

“It’s hard for me to talk about a legacy or a mystique,” Kennedy once said during an interview in 1993. “It’s my family. It’s my mother. It’s my sister. It’s my father; we’re a family like any other.”

Ironically, Kennedy’s premature death seemed to have reinforced this heavy — some might say, dark — “legacy or mystique” that had eluded his personal experience.

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In memory of his brief but full life, here are some of Kennedy’s biggest moments captured in photographs.