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March 17, 2016 01:00 PM

Frank Sinatra Jr., one of the most visible torchbearers of his father’s legacy, died Wednesday at 72.

Sinatra the younger was born Jan. 10, 1944. By the time he was 6, his parents had divorced. His father’s heavy performance schedule – something like two films and four albums a year through the 1950s and ’60s – meant that the pair didn’t have a close relationship during Jr.’s early life: “He was a good father as much as it was within his power,” he told The Guardian diplomatically in 2012.

Regardless, Jr. followed in his father’s footsteps. He’d studied music formally since the age of 5, and became a gifted pianist, singer and arranger by his teens. Part of his education included informal apprenticeships under the likes of Duke Ellington and Nelson Riddle, his father’s longtime arranger.

It was, unfortunately, a non-musical act that would cast the longest shadow over Sinatra Jr.’s career: At 19, he was kidnapped from his Nevada hotel room. He was held for four days before his father paid the $240,000 ransom. Three men – Barry Keenan, Johnny Irwin and Joe Amsler – were eventually arrested and served time for the crime.

Sinatra Jr.’s kidnapping remains fascinating over 50 years later. “The criminals invented a story that the whole thing was phony,” he told The Guardian, a fabrication that mutated into the idea that Sinatra’s father had concocted the whole thing to further his son’s career and one that continued to haunt him for years. (The rumor later inspired an episode of Hawaii Five-0.)

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Keenan in particular continued to pop up in the spotlight. A childhood friend of Sinatra’s daughter Nancy, he recalled to PEOPLE in 1998 that he saw the kidnapping as a “borrowing,” and explained he’d intended to collect the ransom, invest it, and repay Sinatra – with interest. “In my demented state,” he said, “I saw it as a business deal.” (He admitted to being under the influence of alcohol and Percodan at the time.) Keenan later challenged California’s “Son of Sam” law – which bars criminals from making money off their crimes – in court, arguing that he should be allowed to sell the story of the kidnapping to Columbia Pictures for a movie.

Between the kidnapping and his father’s fame, Sinatra Jr. was acutely aware of his place in history. “Over all these years, I have never had a hit movie, never had a hit television program and never had a hit record,” he told The Guardian. “I have made no mark of my own creation.” But, he added, “My lack of success does not trouble me at this stage in my life, no. When I was younger, sure, I wanted to have some degree of, shall we say, identity. But it never came.”

But his father clearly saw something in his son’s talents, bringing him into the fold in 1988 to conduct his orchestra. The younger Sinatra spent the last seven years of his father’s life touring with him.

“I had heard indirectly, because I was not close to it, that he had gone through a series of orchestral conductors,” Sinatra Jr. told NorthJersey.com. “And one afternoon in the middle of 1988 he called me. ‘Why don’t you come out and conduct for me?’ I said, ‘You can’t be serious.’ He said, ‘I’m dead serious. I can’t get these guys to give me what I want to get. Maybe another singer can understand what a singer is trying to do.’ I took that as a terrific compliment.”

“I didn’t expect anything – no quarter and no indulgences,” he continued. “If he had been unhappy with my efforts he was certainly within his rights to replace me. And fortunately he never did.”

“Sinatra the younger not only put his own career on hold to become his dad’s conductor but he became Sr.’s closest confidant, his truest friend,” Rod McKuen, a friend of Sinatra Sr. for 35 years, concluded of the pair’s relationship at the end of the elder’s life.

Despite that, the younger Frank remained haunted by his father’s legacy. In 1993, they recorded “Chicago” for the Sr.’s Duets album, though Jr. told PEOPLE in 2013 that “It was the wrong thing to do.”

“The premise of the Duets album was to have Frank Sinatra sing with young artists who were big successful record sellers,” he elaborated. “I never was. It was nothing but nepotism and it always embarrassed me. I did not belong on those records. I was delighted to do it, but I didn’t belong there.”

The younger Sinatra eventually settled into his legacy, touring with an orchestra that included members of his father’s band and was simply called Sinatra Sings Sinatra. He dutifully collaborated with his father’s acolytes, including Family Guy creator Seth MacFarlane, who at one point studied with Sinatra Sr.’s vocal coach and had Jr. on the show repeatedly to sing duets with Brian, the family dog MacFarlane voiced.

Frank Sinatra Jr. in 2014
Manny Hernandez/WireImage

That Jr. died on tour, still playing his father’s music, was perhaps inevitable. But if it was a foregone conclusion, he made his peace with it years ago. “If the audience comes, and likes what I do, then that’s enough for me,” he told the Guardian in 2012. “I’ll settle for that.”

Reporting by SCOTT HUVER

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