Dean Martin’s Daughter Revealed Her True Feelings About Him – And Cleared Up A Long-Running Rumor

There’s a decades-old rumor about Dean Martin that just won’t quit. And the legendary crooner did little to refute it while he was alive. In fact, he positively encouraged it. One person who’s well qualified to shed light on the story is the Rat Pack star’s daughter, Deana Martin. Which she did, in an interview with Fox News. And as it turns out, the truth is pretty shocking.

Beloved songs

Even if you aren’t familiar with the wise-cracking, good-time-guy public image of Dean Martin, you’ll likely know his music. For example, if someone were to sing, “When the moon hits your eye like a big pizza pie,” there’s a good chance you’d warble back, “That’s Amore!” This popular track has featured in everything from TV commercials to massive shows such as Friends. It’s part of the pop-cultural fabric.

Famous friends

You might also know that Martin was part of the legendary group of pals known as the Rat Pack. He, Frank Sinatra and Sammy Davis Jr. sold out Las Vegas venues in the 1960s with their iconic shows – which are still successfully touring with impersonators to this day. But what you might not know is that Martin’s daughter, Deana, is a famous singer in her own right.

Like father, like daughter

Yes, proving that she’s a chip off the old block, Deana – the youngest of Martin’s four kids with his first wife, Betty McDonald – has forged a glittering career in show business. Both an actor and singer, she began performing in theater before moving into movies and television. Her first TV appearance came in 1966, when she starred with her famous dad on The Dean Martin Show.

Becoming a star

Performing with her high-profile pop and equally big names such as Sinatra got Deana hooked on being an entertainer. She became a regular on Martin’s show, as well as recording a handful of hits throughout the 1960s. But it wasn’t until after her father’s death in 1995 that the singer’s music career really took off. Her 2006 album Memories Are Made of This featured covers of her dad’s hits such as “That’s Amore” and “Everybody Loves Somebody.”

Continuing the legacy

The album also featured the charming standard “Time After Time” – not to be confused with the Cyndi Lauper track – with Martin’s one-time sidekick Jerry Lewis. The magical mix saw the album make it to the downloads top 10 and stay there for an incredible 40 weeks. Deana’s since toured the globe with a repertoire including her dad’s hits and jazz classics.

Racking up the hits

Further hit albums followed for the singer, including a 2011 compilation of festive favorites, White Christmas, featuring a duet with Andy Williams. Deana also released another record in 2016 called Swing Street, laid down at the very studio in which her dad had made his 1955 chart-topper “Memories Are Made of This.”

In memory

And speaking of memories, Deana marked what would’ve been her beloved father’s 100th birthday in 2017 with special performances in Las Vegas and Ohio. Talking at the time to the Los Angeles Times about the shows, the star said, “There’s, of course, a lot of Dean Martin music plus ‘Uncle’ Frank Sinatra, ‘Uncle’ Sammy Davis Jr., Bobby Darin, a little Ella Fitzgerald,” she said. “It’s all the great songs and then, of course, my own songs.”

Do we really know Dino?

So it’s clear that Deana owes a lot to her dad “Dino” and his musical peers. Keeping their legacies alive is obviously important to her, too. But what of the singer’s relationship with her dad? Were they close? And is the public image of the Rat Pack star in line with the father she remembers? We already know there’s one widely believed rumor she’s keen to address...

Career beginnings

And there’s also the little-known fact that Martin’s birth name was actually Dino. Yep, he actually began his performing career with the handle “Dino Martini,” inspired by the famous tenor Nino Martini. It was musician Sammy Watkins who inspired the future star to change his name to Dean Martin. The caramel-voiced crooner performed with Watkins regularly until WWII intervened.

The funny one

Despite some Hollywood interest, Martin’s movie career failed to take off. And so he stumbled into comedy after becoming great pals with comedian Jerry Lewis. They established a successful singing/comedy double act that scored them a run at NYC’s Copacabana club. You might have heard of that one, thanks to a certain Barry Manilow song!

Fame and fortune beckon

The Martin/Lewis pairing grew into a multi-million-dollar partnership that lasted a decade. But after things turned sour, the duo went their separate ways and Martin set his sights on Hollywood stardom once again. He met his long-time pal Sinatra when the two appeared in Some Came Running in 1958. They would be paired again in a number of other films, including the original Ocean’s 11. Martin met another future Rat Pack buddy, Sammy Davis Jr. on a movie set, too.

Superstar singer

Now a bona fide movie star, Martin was also proving his prowess as a singer. Soon he was crooning alongside Sinatra and Bing Crosby – and doing a good job of it, too. His hit “Everybody Loves Somebody” even replaced The Beatles’ “A Hard Day’s Night” at the top of the American charts. No mean feat! And Elvis Presley was apparently inspired by Martin’s vocal style when he recorded “Love Me Tender.” Wow.

King of Cool

“Elvis idolized my dad,” Deana Martin told Fox News in 2017, “I remembered meeting Elvis and he was the one who told me my dad was the king of cool. I’ll never forget that.” Martin’s daughter also recalled how the Rat Pack were regular visitors to her father’s Beverly Hills residence and became like “uncles” to her.

“Uncle Frank”

In fact, Deana credits “Uncle” Frank Sinatra for being the person who really taught her how to sing, not – surprisingly – her star-singer dad. She told Fox News, “Frank Sinatra was really the one who turned the light on for me. I said to Frank, ‘How do you do it?’ He said, ‘Oh, by taking a big breath, I push from the diaphragm, and I can tell before a note comes out if I’m going to be on pitch or not.’”

The Rat Pack is born

Martin’s daughter continued, “I said, ‘Really, does my dad do that?’ He said, ‘No, he has no idea what he’s doing. He just does it.’” The “Volare” singer’s friendship with Sinatra led to them establishing the Rat Pack towards the end of the 1950s. The group, which also included Sammy Davis, Joey Bishop and Peter Lawford, became legendary. Their Las Vegas shows were raucously entertaining, with risqué humor that focusing on Davis’ race, Sinatra’s love of women and Martin’s liquor-swilling.


Yes, the crooner had begun to cultivate a reputation for being a loveable drunk. And The Dean Martin Show, which Deana would later become a regular on, did nothing to discourage this image. In fact, it did the opposite. Martin would flirt outrageously with his female guests and slur insults at others – and audiences loved his humor.

Flawed hero

It was actually this charming stage presence that inspired daughter Deana to follow in her father’s footsteps. She recalled to Fox News, “My dad would walk out in a tuxedo with a red pocket square. He would sing and he was funny. He looked great and the audience loved him. It was like magic. So I always wanted to be an entertainer.”

Introducing The Stones

Having a parent in show business clearly had other perks, too. Like the occasion Deana got to see “newcomers” to the biz, The Rolling Stones, at a show Martin was compering. “I was 16 when my dad called me on the phone. He said, ‘I don’t know who they are, but I think you and your sisters would want to come down here and see these guys. It looks like they just got off the boat!’”

Lightning wit

“When we got there, my dad comes out and says, ‘Alright ladies and gentlemen, we’ve got this next group. I’ve been rolled and I’ve been stoned, but I’ve never seen anything like this!” Martin definitely had one heck of a sense of humor! But as we all know, even the coolest of parents can still be embarrassing when you’re a teenager.

Cringe moment

Deana can certainly testify to that, as she still remembers a particularly awkward moment involving her dad and a certain Beatle. She recalled to Fox News, “My dad went to a party and Paul McCartney was there. He came up and said, ‘Hi John, it’s nice to meet you.’ Paul said, ‘I’m not John, I’m Paul McCartney.’ Dad responded, ‘I call everybody John.’ And he came back home and told me this. I was like, ‘Dad, you’re embarrassing me!’”

Beating The Beatles

Ever the joker, Martin knew the magnitude of The Beatles’ star-status really. So when his song “Everybody Loves Somebody” replaced the Fab Four at number one on the Billboard chart, the singer knew what it meant. “Nobody else could do that,” Deana told Fox News. “Not Frank Sinatra or Elvis Presley. Dad sent two telegrams, one to Presley and another to Sinatra. And it just said, ‘I did it.’”

Devoted father

So, given that Martin was forever playing the clown on stage, was he like that with his family at home? Not according to Deana. She says the “Ain’t That a Kick in the Head” singer was actually a pretty tough parent to his seven biological kids, from two marriages. “He was an Italian father,” Deana stated.

Tough love

Deana continued, “He would go, ‘These are the rules. You make your bed in the morning, you clean up, you come straight home after school, you do your homework, you’re on time for dinner. And this is it. If you don’t want to live by those rules, there’s the door.’ I would go, ‘Dad, I’m 9!’ He’d say, ‘Come on! Rules are rules!’ We never wanted to do anything to disappoint him.”

The truth behind the rumors

And what of the longstanding rumor that Martin was a drunk? Is this the man Deana knew? No, as it turns out. Dino’s daughter revealed in a 2016 interview with the Los Angeles Times that it was in fact apple juice – not liquor – that her dad was seen knocking back on stage.

All an act

Deana told Fox News, “I’m amazed when people come up to me after a show and say, ‘How could your dad do so much work when he was always drinking? My jaw drops. Because that was his gimmick! I guess he really was a good actor because people always thought that was true… I get a chill when people say that… I still have to clear it up.”


So how did this “gimmick” come about? “It was like Jack Benny who had the violin thing and made fun about being cheap,” Deana explained to the Los Angeles Times. She went on, “Dad was so handsome, so debonair. They just thought, ‘We’ll put a drink in his hand and a cigarette.’ Every man wanted to be him, and every woman wanted to be with him.”

Family man

But the real “Dino,” the family man, was very much the wholesome, devoted husband and dad, according to Deana. “He would be home for dinner every night,” she added. “He would come home, and he and mom would have their one cocktail at the bar. He was kind. He was so different from what everybody thought he was.”

Incredible legacy

Given all of this, it understandably makes Deana pretty mad when people still float words such as “alcoholic” in reference to her father. She told Fox News, ““After all of these years, after the body of work he accomplished from singing in nightclubs to Martin and [Jerry] Lewis, the greatest comedy team ever.”

Fighting the gossip

“And all the movies, all the albums, all the number one hits,” Deana continued. “And the TV show for 20 years. How can people even think that? Obviously that’s not true! So when people say weird things, I just smile. Because that’s not how it happened.” We can certainly understand why she feels defensive of her beloved dad. After all, wouldn’t anyone feel the same in a similar position?

Right on the nose

But there are some tales about her father that the singer’s willing to admit are based in reality. Such as the one that the Rat Pack star supposedly had a nose job before finding stardom. Reportedly, the surgery was paid for by an unnamed donor whom Martin later reimbursed. “He did have one. I have pictures!” Deana revealed.

All about the swing

Alongside his love for his family and performing, it seems Martin had another amore in his life: golf. “He would go to bed early just so he can get up early and play golf. In fact, he told me, ‘Deana, the reason why I work so hard is so I can play with all you kids and play golf.’ He was a scratch golfer at one point.”

Secret phobia

And there are some lesser-known facts about Dino. In her interview with Fox News, for instance, Deana revealed that her dad was claustrophobic. “He never wanted to go in elevators,” she said. “So when he would go to hotels, whether it was the MGM Grand or whatever, his suite always had to be on a low floor so he [could] just walk up the stairs.”

Taking a downturn

Early in the 1970s, though, both Martin’s career and personal life began to falter. Just as his 24-year marriage to second wife Jeanne ended in the divorce courts, his deal with the Riviera hotel in Las Vegas also concluded. It was apparently a disagreement over the conditions of his contract that led Martin to walk. Instead, he took up with the MGM Grand Hotel & Casino, where he became the headline act.

Flops and failures

The star’s movie career was hitting the skids, too. Mr Ricco, a 1975 legal drama featuring Martin in his final leading role, received a critical panning. As did 1981 action romp The Cannonball Run, in which Martin joined an all-star ensemble cast, though the latter was at least a huge success commercially.

Finding love again

The entertainer gave marriage a third try in 1973, tying the knot with 20-something receptionist Catherine Hawn. It would sadly end in another divorce just three years later. There was then a fleeting engagement to former Miss World USA, Gail Renshaw. But in a rather lovely twist of fate, Martin would reunite with his second wife and the love of his life, Jeanne.

Making amends

There were other reconciliations, too. During a 1976 charity telethon hosted by Jerry Lewis, guest Frank Sinatra surprised the heck out of Lewis by walking on with his old friend Martin. The two hadn’t spoken since their working relationship had broken down years earlier. Sinatra, it seems, had been dealing with some difficulties in his personal life. But the live reunion, which saw the men hug out their differences, thrilled the TV audience and brought in donations at an unprecedented rate.

A tragic loss

In 1988 Martin embarked on a tour with Rat Pack pals Davis and Sinatra. It was partly to help him get over the loss of his son Dean, who’d tragically died in a plane crash the previous year. But Vegas veteran Martin felt uncomfortable performing to stadium crowds, so the tour ground to a halt. His final couple of television appearances came in tributes to his Rat Pack buddies, though – celebrating Davis’ 60th anniversary and Sinatra’s 75th birthday respectively.

Passing of an icon

On Christmas Day in 1995, Martin died aged 78 due to respiratory problems. His ex-wife Jeanne was by his side as he passed away at his home in Beverly Hills. She told People magazine shortly afterwards that, poignantly, the singer’s last words were, “You’re the only girl I ever loved.” The lights of Las Vegas were dimmed when the news of Martin’s passing broke.

Memories are made of this

One of the people who remembers him most fondly is of course daughter Deana. As well as keeping the memory of his music alive, she told Fox News that her father’s never far from her thoughts. “I’m always thinking about dad, what he went through in his life and how the world has changed,” she said. “He was a sweet, generous man who would just get up and do his thing.”

Sinatra’s the wild one

If Martin’s on-stage persona was wilder than his life at home, then the opposite seems to be true for Sinatra. Various rumors have always surrounded the star. While the singer officially has three kids from four marriages, his reported philandering means that other potential children have cropped up over the years. In fact, three of the women who claim to have had extramarital relationships with Sinatra have said that he is the biological father to their offspring.

Many, many children

A resident of Sedona, Arizona, named Julie has maintained that she is Sinatra’s daughter, for instance, and she even changed her legal surname to that of her alleged father in 2000. Julie has said that her mother, a Las Vegas hostess named Dorothy Bunocelli, engaged in a seven-year affair with Sinatra in the 1940s. And, apparently, Dorothy finally told her the truth of her parentage a few years before the mom passed away.

More children

Then there was an Australian woman named Deana, who has also gone under the last name of Sinatra. Her mother was the German actress Eva Bartok, who reportedly had an affair with Sinatra while he was married to Ava Gardner. And Deana asserts that she and her mother made efforts to meet Sinatra in person, including sending him a letter when she was 15 years old.

A cold response

Unfortunately, though, Deana received a response saying that Sinatra wasn’t open to bringing another child into his family. And not only was she deeply hurt by this reply, but those words also apparently altered her perception of the star. “I don’t think he was a man of high morals and values. That’s my feeling from where I stand,” Deana told Australian morning TV show Studio 10 in 2015.

Puzzling parentage

Pulitzer Prize-winning investigative journalist Ronan Farrow has also long been rumored to be another illegitimate child of Sinatra. Indeed, in 2013 his mother, actress Mia Farrow, told Vanity Fair that it was “possible” Sinatra was her son’s father rather than writer and director Woody Allen.

"We're all Frank Sinatra’s son"

Furthermore, during Farrow’s November 2019 appearance on Real Time with Bill Maher, the host was bold enough to question his guest’s parentage. In a seeming reference to the writer’s reporting on the Harvey Weinstein scandal, Maher even quipped, “There’s no one more #MeToo-y than Frank Sinatra.” And while Farrow wouldn’t be drawn into the conversation, he did previously joke in a 2013 tweet, “Listen, we’re all ‘possibly’ Frank Sinatra’s son.”

A strong temper

On top of the claims of affairs and illegitimate children, however, there have also been negative stories about Sinatra’s personality. It’s been said, for example, that he had a hair-trigger temper. His fourth wife, Barbara, has also noted the “Jekyll-and-Hyde aspect to Frank,” while Mia Farrow once called him a “24-carat manic depressive.”

A nasty side

Over the years, it’s additionally been reported that Sinatra was prone to hurling things at loved ones and friends during arguments. Yes, apparently, the singer once threw a glass pitcher of water at drummer Buddy Rich’s head. Sinatra had previously accused Rich of making errors in his drum solo – a complaint to which the musician had responded with name-calling. And by all accounts, the pitcher only just missed its intended target.


Furthermore, it’s alleged that Sinatra once threw a heavy telephone at businessman Frederick R. Weisman in the Beverly Hills Hotel, with this assault reportedly fracturing Weisman’s skull. The star’s second wife, Ava Gardner, also suggested that a long crack in the porcelain of one of their bathroom sinks had been his handiwork. According to Gardner, Sinatra had previously heaved a champagne bottle at her, but the missile had ultimately damaged the basin instead.

Sore loser

And in her book Lady Blue Eyes: My Life with Frank Sinatra, Barbara wrote about a frightening incident that she claimed to have had once experienced. After Sinatra’s team had lost a game of charades, the singer had allegedly picked up the brass clock that Barbara had been using to time-keep. His former wife went on to write, “I think [Frank] wanted to hit me with it. He threw it against the front door, and it broke into a thousand pieces.”

Mafia connections

Sinatra’s extensive connections with the Mafia are potentially even more discomforting than his temper, however. And the associations appear to begin close to home, too. You see, Sinatra’s first wife, Nancy, was the cousin of John Barbato – a captain in the Genovese crime family. Famously, the Genoveses were one of the five clans that once controlled organized crime in New York and New Jersey.

Willie Moretti

Consequently, Sinatra is said to have links to infamous Genovese underboss Willie Moretti. It’s said, for example, that Moretti helped Ol’ Blue Eyes during the early part of his career by booking gigs in New Jersey nightclubs. In exchange, the mobster simply wanted a cut of the singer’s payment. It’s even alleged that Moretti threatened to shoot bandleader Tommy Dorsey dead in 1941, as Dorsey was supposedly trying to hold Sinatra to a contract that he no longer wished to honor.

A better path

In the 1940s, however, Sinatra decided to pursue an acting career. And he would go on to achieve huge success in the field, too. Perhaps owing to his stardom, Sinatra ultimately became great friends with cinematic royalty such as Cary Grant, while he famously wooed some of the most famous actresses of the day. Back then, though, a more sinister character was also floating around Hollywood circles, and ultimately the singer is said to have found himself in his thrall.

A gangster's influence

In the late 1930s, New York gangster Benjamin “Bugsy” Siegel moved out to California to set up gambling and protection rackets. And thanks to his charm and charisma, he was soon embraced by Hollywood celebrities. But while Siegel was a real mobster who was known for his propensity for violence, that didn’t seem to put off some of the actors with whom he partied. Sinatra almost seemed to idolize the man, in fact.

Bragging about Bugsy

Jo-Carrol Dennison – who back then was the wife of actor Phil Silvers – has since spoken of her husband and Sinatra’s admiration of Siegel. “They would brag about Bugsy,” she said, “what he’d done and how many people he’d killed.” She also claimed that she’d always remember “the awe Frank had in his voice when he talked about him. He wanted to emulate Bugsy.”

Watched by the FBI

Willie Moretti and Bugsy Siegel were apparently far from Sinatra’s only links to the mob, however. You see, the Federal Bureau of Investigation (FBI) kept tabs on Sinatra for more than four decades. And the resulting file – which was made public following the star’s death in 1998 – contained a mammoth 1,275 pages of documents concerning his friendships with known Mafia personnel.

What's the truth?

Yes, throughout Sinatra’s career, there was a substantial amount of documented evidence of him interacting with known Mafia figures. His FBI file even had one heading that read, “Associations with criminals and hoodlums.” Yet while Sinatra admitted to knowing mobsters and was regularly photographed with organized crime personnel, he fiercely denied any true involvement with the mob.

Merely coincidence

And in a 1965 interview with Walter Cronkite – which was later sold as a documentary titled “Sinatra: Off the Record” – the star explained away these supposed ties to the Mafia. In essence, he believed that they had simply come by way of his life as an entertainer. “In theatrical work, in nightclub work, in concerts. So, wherever I might be. In restaurants, you meet all kinds of people,” Sinatra said.

FBI weren’t convinced

Sinatra continued, “So… there’s really not much to be said about that. And I think the less [said] the better.” However, the FBI certainly believed that there may have been more to the claims than Sinatra would admit. Agents apparently even floated the idea of bugging Sinatra’s home, although FBI supremo J. Edgar Hoover ultimately decided against proceeding down that path.

Wrong place, wrong time

A mob-related controversy in 1947 didn’t exactly help dispel any rumors, either. In that year, Sinatra was snapped in Cuba while attending an event celebrating Lucky Luciano’s release from prison. And Luciano wasn’t simply a low-level hood. In fact, owing to his part in the formation of the Commission – the Cosa Nostra’s governing body – he has been called the father of modern organized crime in America.

Too close for comfort

Unfortunately for Sinatra, then, he was pictured in two different spots with Luciano. One snap shows him with his arm around the crime boss’ shoulders on a hotel balcony, while another sees him apparently partying with Luciano in a Havana nightclub hotspot. And Sinatra was even photographed getting out of a plane while accompanied by Al Capone’s cousins Rocco and Joseph Fischetti. These two men were both known as big players in illegal gambling rackets.

Singing for the mobsters

Yet Sinatra later excused his presence at the event as a misunderstanding. He reasoned that he didn’t know he would be attending what was effectively a Mafia conference; then, once he had realized the true nature of the attendees, it had been too late to back out. Still, Sinatra sang for the mobsters, and despite his subsequent protestations, witnesses claimed that he never seemed uncomfortable with the generosity shown by the criminals.

Working with the FBI

Then, only three years later, Sinatra was experiencing a low point in his career, with the popularity of his records having dwindled drastically. And, interestingly, a 1950 note in the FBI file details contact from someone who was apparently close to the star. This person, whose name is redacted, reportedly said, “Sinatra feels he can do some good for his country under the direction of the FBI.”

No deal

The individual in question is also said to have put forth the idea of Sinatra “going anywhere the bureau desires and contacting any of the people from whom he might be able to obtain information.” This was a thinly veiled way of saying that Sinatra may be willing to snitch on his mob friends. However, FBI associate director Clyde Tolson wrote, “We want nothing to do with him” – and Hoover agreed.

Still heavily involved

Sinatra’s career went on to recover in the 1950s, although his mob connections still seemed to run deep. For one, he was reportedly close friends with Chicago Mafia boss Sam Giancana. And in a 2000 interview with 60 Minutes, Sinatra’s daughter Tina alleged that, in 1960, her father had acted as a middleman between Giancana and then-Senator John F. Kennedy’s campaign for president.

Helping the Kennedys

Apparently, Kennedy’s father, Joseph, felt that the Mafia could help deliver his son the labor union’s vote in the 1960 West Virginia primary. And Tina alleged that Joseph had subsequently approached her father because he knew of Sinatra’s connection to Giancana, whose outfit could strongarm the votes. She claimed, moreover, that it was considered better for JFK if his father didn’t approach the mob directly – which is exactly why Sinatra had been brought in.

A price to pay

Fortunately, Giancana was all too happy to help out the Kennedys, according to Tina. Indeed, she said that he had told Sinatra, “It’s a couple of phone calls.” After JFK became president, however, his administration spearheaded a countrywide clampdown on the Mafia. And, reportedly, Giancana was furious, as he felt that the Kennedys – and Joseph in particular – owed him.

Making it up to Giancana

This is where the alleged use of Sinatra as a liaison came in handy for the Kennedys. Tina claimed that Sinatra was able to calm Giancana down by reputedly saying, “No, I owe you. I asked for the favor.” He then made it up to his mob boss friend by playing two shows per night for eight consecutive days in Giancana’s Chicago club, the Villa Venice.

Still suffering the consequences

However, Sinatra’s connection to Giancana would eventually cost him when, in 1963, the mobster was seen at the Lake Tahoe casino Cal-Neva Lodge. Sinatra owned the place, you see, having purchased it in 1960. And unfortunately for the singer, Giancana was on Nevada’s “List of Excluded Persons,” meaning he was banned from casinos in the state. Ultimately, then, Ol’ Blue Eyes lost his gaming license as a result.

Other connections

But Sinatra supposedly also had connections to other mobsters. Indeed, retired FBI agent Sam Ruffino talked about one of those apparent associations when speaking with author Scott M. Burnstein. According to Ruffino, as the FBI monitored Detroit Mafia figures Anthony and Vito Giacalone, the two were regularly spotted mingling with Sinatra.

Being watched

“It was like clockwork,” Ruffino said in 2018. “A few times a year, we’d trail the Giacalones to the airport to pick up Sinatra. They’d spend the weekend together socializing before and after his shows.” He also claimed that Sinatra and his mob pals would always be the last to leave any event. And, apparently, the singer himself was quite laissez-faire about the true nature of the men with whom he surrounded himself.

Odd choice of friends

Ruffino noted that Sinatra made no apologies for his associates, adding, “Those were his friends. The fact that they were known hoodlums and murderers didn’t matter to him.” He added that Sinatra “was going to hang around with who he wanted to hang around with.” After all, it didn’t make him a criminal by association.


Meanwhile, the FBI file further revealed that the bureau was also very concerned about Sinatra’s alleged ties to communism. The singer publicly defended people who had been accused of being communists, for one, along with supporting anti-racism causes. Even so, this line of investigation similarly never led to prosecution of any kind.

A kidnapping

Plus, despite the fact that he was being constantly monitored by the FBI, Sinatra was able to turn to the bureau for help in 1963 when his son, Frank Sinatra Jr., was kidnapped. Agents subsequently advised Sinatra to pay the requested ransom, which would then enable them to trace the money to the culprits. And, fortunately, Frank Jr. was returned safely, with all three of his kidnappers eventually caught and then convicted.

Sinatra knew everything

Yet Sinatra was fully aware that the FBI was keeping tabs on him. Indeed, in 1979 and 1980 he made official requests to take a look at the bureau’s file. And thanks to the Freedom of Information Act, Sinatra duly received those documents, meaning he was able to see exactly what the FBI was cataloging about his activities.

The FBI needed Sinatra

Then, in 1998, The Washington Post writer Jeff Leen gave an insightful analysis of Sinatra’s curious relationship with the FBI. More specifically, he claimed that though the bureau’s interest in Sinatra had initially come as a result of “suspicion and contempt,” the relationship developed into a very odd co-dependency. In fact, Leen felt that the FBI needed Frank Sinatra and vice versa.

"A threat must be tracked"

Leen characterized Sinatra thus, “What every law enforcement agency needs to stay engaged and in business: a threat that must be tracked.” In turn, he wrote, “The FBI gave Sinatra what every celebrity needs: protection from lunatics and extortionists.” And although the bureau could never conclusively prove that Sinatra took part in any illegal activity, it took his “comings and goings among the criminal elite” very seriously indeed.