In a week where John F. Kennedy Jr. would have celebrated his 60th birthday, his friends are lamenting that the world never got to see what the dashing presidential son would have become.
The son of former President John F. Kennedy died at 38 on July 16, 1999, when a plane he was piloting crashed into the Atlantic Ocean, killing him along with his wife, Carolyn, and his sister-in-law, Lauren Bessette.
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"His legacy was really about who he would've become," friend Brian Steel, a former assistant district attorney in Manhattan with Kennedy, said on TODAY Tuesday.
"But I just think America and maybe the world would have been a better place."
His death marked the latest tragic loss in a family that has experienced much of it over the generations. Kennedy Jr. himself was famously pictured on his third birthday saluting the casket of his father following the president's assassination in Dallas in 1963.
This is a solemn week for the Kennedy family, as Kennedy Jr.'s 60th birthday would've been Wednesday, while Sunday marked the 57th anniversary of his father's assassination.
A line from the younger Kennedy's funeral reminded everyone how he was gone too soon when Sen. Edward Kennedy said during his eulogy that his nephew did not live long enough to comb a gray hair.
"I think that was probably the line that took us all out," Rosemarie Terenzio, his former executive assistant at George magazine, said on TODAY.
"That was the crushing sort of gut punch line," Steel said. "Now you look back, and you think of what might have been."
Kennedy had been mulling over a foray into politics, the stock in trade of his famous family, but had not yet made the leap.
"I think anytime you go into politics, you have to make sure the rest of your life will accommodate that decision," he told NBC's Tom Brokaw in 1995. "I have a few years to make that decision."
He had become a New York City tabloid fixture as one of the world's most debonair bachelors before marrying Carolyn Bessette in a fairy tale wedding in 1996.
A run for high-profile political office in New York was most likely in his future with an eye on one day returning the Kennedy family to the White House.
"There's no doubt he was thinking about running for governor," Steel said. "We had that discussion a couple times in the months before he passed away. He had given sort of fleeting thought for running for that Senate seat in 2000.
"He said he wasn't interested. When I asked him why, he said, 'No one in my family has been a governor, and I'd sort of like being a chief executive.'"
"He was being asked also to run for mayor at one point," Terenzio said. "And I remember saying to him, 'Why wouldn't you run for mayor? I mean, you would certainly win it pretty much hands down.' And he said, 'How many mayors do you know that become president?'"
Being at the intersection of politics and popular culture in New York in the 1990s also meant crossing paths with now-President Donald Trump during his days as a real estate developer.
"I think John was amused by him and just sort of thought he's this flamboyant, New York attention-seeking, egomaniac kind of guy," Terenzio said.
"I wouldn't say they were friends or friendly, but I don't think he would have predicted he'd be president today," Steel said.
The fascination with Kennedy Jr. continues to this day.
"If John knew he would be gone at 38 years old, I don't think John would have wanted to be forgotten," Terenzio said.
"If everyone forgot him on his 60th, I think that would disappoint him for sure," Steel said.
There is a whole generation that has now grown up without knowing Kennedy Jr. as a public figure, but his memory lives on.
"I mean, there was no one that compared in the world to John," Steel said.
"Everything that he did with his power, his fame, it was all about some greater good," Terenzio said. "The way that he gracefully took that mantle and lived an honorable life full of integrity — and because of what we all want, which is somebody or something to look up to and to be proud of."