The Truth About Doris Day’s Off-Screen Life Proves That She Was Nothing Like Her Hollywood Persona

"Whatever will be, will be," crooned the elegant, perfectly coiffed Doris Day during the opening credits of her talk show. Audiences around the globe remember the late cinematic leading lady for her effortless grace and unflappable cheeriness. The conservative actress was labeled a safe, wholesome figure, but her most admirable trait was perhaps her ability to power through misfortune. Time and time again, Doris grappled with tragedy and pressed on, showing a far grittier side than we saw in any of her movies.

Innocent image

Back in the Golden Age of Hollywood, though, Day was widely regarded as an innocent alternative to the vampish Marilyn Monroe. In the press, she was painted as a woman plenty of men would love to make their wife. Monroe? She was a woman guys just wanted to seduce. And Day seemed more than happy to live up to this reputation – on camera, at least.

Hollywood everywoman

So, throughout the 1950s and early 1960s, Day charmed audiences everywhere with a string of roles that showcased her natural singing talent and sense of humor. But away from the movie lots, the Hollywood everywoman was practically a different person. She lived a life that saw much more tragedy than comedy.

Tragic life

These setbacks started when Day was still young. For one, her parents, William and Alma, had tragically lost their first son, Richard, before Day was born. Not only that, but the couple ultimately separated when the future movie star was only in her teens. And her ambition of becoming a professional dancer? That was also derailed when one of her legs was seriously maimed in an automobile accident.

Untapped talent

But this last traumatic event proved to be somewhat of a blessing in disguise. You see, while Day recuperated from her ordeal, she discovered a previously untapped talent. Inspired by Ella Fitzgerald – an artist she regularly heard on the radio – she began singing. And after receiving voice tuition, Day managed to land a gig on Carlin’s Carnival – a show on the radio network WLW. Yep, she managed to make some good lemonade out of those lemons.

On the road

Even better, one of the show’s listeners was bandleader Barney Rapp, and he was pretty impressed with what he heard. So, he offered Day – then known as Doris Kappelhoff – a job with his ensemble. That was a big break that set the fledgling performer well on the way to stardom. And after adopting her more familiar stage name, the future actress went on to work with Bob Crosby, Jimmy James and Les Brown.

Another level

Day had great success as a singer, too. In 1945 she scored her first hit with World War II anthem “Sentimental Journey.” She also graced the Billboard Top Ten with such family-friendly songs as “Till the End of Time,” “I Got the Sun in the Mornin’” and “My Dreams Are Getting Better All the Time.” But it was Day’s version of “Embraceable You” that helped take her career to another level.

Audience favorite

Songwriters Sammy Cahn and Jule Styne were so enamored with Day’s performance on the song that they put her name forward for a part in a movie. The flick was Michael Curtiz’s 1948 movie Romance on the High Seas, and Day was given the role despite having no previous experience. But she was probably glad she took the plunge! She became a star of the big screen as well as the charts when the film and its key song, “It’s Magic,” both became hits.

Girl next door?

Now, Day was well on the way to becoming the quintessential girl next door. She refined her sugar-sweet image through sentimental musicals such as Tea for Two, On Moonlight Bay and I’ll See You In My Dreams. Based on the life story of songwriter Gus Kahn, the last of these pictures became a record-breaking box-office smash. Then in 1953, Day landed perhaps the defining role of her career.

Career high

What else but Calamity Jane? Day cemented her place in Hollywood history with her whip-crackin’ turn in the movie of the same name. One of its most famous numbers, “Secret Love,” even picked up a Best Original Song Oscar. And Day’s golden streak continued after that, too, with Lucky Me and the Frank Sinatra vehicle Young at Heart.

More to her

However, Day was keen to prove that she could do more than play the girl next door. In 1955, then, she appeared on screen as vocalist Ruth Etting in the drama Love Me or Leave Me – a role for which she would receive critical acclaim. She also worked with the legendary Alfred Hitchcock and James Stewart in the mystery The Man Who Knew Too Much and starred in the noir thriller Julie.

Partnership

In 1957, though, Day returned to more comedic and musical fare with The Pajama Game. She also went on to share the screen with Clark Gable in Teacher’s Pet, Richard Widmark in The Tunnel of Love and Jack Lemmon in It Happened to Jane. And in 1959 she forged a creative partnership with Rock Hudson that ultimately hit box-office paydirt.

Lifelong relationship

Hudson and Day, who would become lifelong pals, first charmed the cinemagoing public in Pillow Talk. Memorably, Day also picked up her first – and perhaps surprisingly her last – Academy Award nomination for her performance as Jan Morrow in the movie. And the popular duo would reunite for similarly endearing romantic comedies Send Me No Flowers and Lover Come Back.

Abrupt end

Day then cemented her status as the era’s number one female star with roles in Please Don’t Eat the Daisies, That Touch of Mink, and Move Over Darling. Penned in part by Day’s son, the latter’s theme song also became one of the actress’ signature hits. As it happens, though, her reign as a box office queen was about to come to an abrupt end.

Out of fashion

You see, as the baby boomer generation’s counter-culture movement began to grow, Day’s innocent and nostalgic pictures fell out of fashion. It didn’t help, either, that she was cruelly labeled “The World’s Oldest Virgin” by the media. And after 1966’s The Glass Bottom Boat, Day’s fortunes changed, as she never again experienced her previous level of success.

Crude roles

The actress also refused several notable roles that would have helped audiences see her in a new light, with arguably the most famous of these being Mrs. Robinson in the 1967 classic The Graduate. Yet Day was displeased by the apparent crudeness of the movie script, and so she passed on the part that would eventually go to Anne Bancroft.

Enough was enough

Then, after showing up in 1968’s With Six You Get Eggroll, Day decided to put a stop to her film career. That said, this fateful decision didn’t see her swear off stardom altogether, as she would go on to front her own eponymous TV show on CBS. During the series’ successful five-year run, Day also hosted her own small-screen specials. But when The Doris Day Show came to an end in 1973, she decided that enough was enough and largely retired from public view.

New life

The star did eventually return to the spotlight in 1985 for chat show Doris Day’s Best Friends, although the Christian Broadcasting Network series was taken off air after just 26 episodes. Nevertheless, she wasn’t completely forgotten in the years that followed. In 1989, for instance, she was honored with the prestigious Cecil B. DeMille Award at the Golden Globes. And in the 1990s a greatest hits compilation – as well as an appearance on the soundtrack to Australian movie Strictly Ballroom – helped introduce Day’s music to a whole new generation.

Charity work

Outside of the entertainment world, meanwhile, Day helped establish Actors and Others for Animals in 1971 before setting up the Doris Day Animal Foundation seven years later. She also co-funded a Horse Rescue and Adoption Center that was named in her honor and was instrumental in the launch of the yearly Spay Day USA. In 2004, then, George W. Bush presented Day with the Presidential Medal of Freedom for services to both showbiz and wildlife.

Lifetime achievements

And Day continued to make her mark in the aughts. In 2008, for instance, she was awarded a Lifetime Achievement Grammy, followed up four years later by a third Grammy Hall of Fame Award. However, the all-but-retired actress was seemingly less interested in receiving an honorary Oscar. She reportedly turned down offers from the Academy on several occasions, in fact – suggesting, perhaps, that she wanted her movie career to stay in the past.

Heart in it

Then, in 2011 – and at the age of 89 – Day went on to score a surprise U.K. top ten hit. A collection of previously unreleased tracks, entitled My Heart, saw the star become the oldest ever artist to achieve such a feat with new material. And four years later, Day was invited by neighbor Clint Eastwood to stage a comeback proper by appearing in his latest film; ultimately, though, the actress politely refused.

New interview

Yet that wouldn’t be the last that everyone heard of Day. In a surprising turn of events, the screen icon agreed to be interviewed by The Hollywood Reporter in April 2019 – shortly after she had turned 97. And when asked what her favorite movie role was, she replied that it had been the lead in Calamity Jane. Day added, “I was such a tomboy growing up, and [Jane] was such a fun character to play. Of course, the music was wonderful, too. ‘Secret Love,’ especially, is such a beautiful song.”

Passing

Sadly, just a few weeks after this rare interview, Day passed away following a bout of pneumonia. Representatives from her eponymous animal charity confirmed the news and that she’d died surrounded by loved ones at her Carmel Valley, California, home. And, unsurprisingly, a whole host of tributes from Hollywood stars past and present then flooded in.

Eulogies

William Shatner described Day, for instance, as “the world’s sweetheart and beloved by all.” Goldie Hawn remarked, meanwhile, “The great Doris Day left us and took a piece of the sun with her. She brightened our lives and lived out her life with dignity.” And fellow Hollywood veteran Carl Reiner recalled of the late star, “Just a week ago, I contacted her and welcomed her to the 97-Year-[Old] Actor’s Club.”

Different story

Naturally, the majority of press reports about Day’s death focused on her golden period as Hollywood’s ultimate girl next door. But while the actress’ life may have seemed picture-perfect on screen, it was a very different story in real life. In fact, Day experienced numerous hardships throughout her glittering career.

Unhappy marriage

During Day’s late teens, for example, she married Al Jorden – a trombonist whom she had first gotten to know while performing with Barney Rapp and his band. Sadly, though, their union was far from a happy one, as Jorden was a physically abusive schizophrenic who very nearly killed the couple’s unborn son. After learning that his wife was both pregnant and unwilling to have an abortion, the musician had viciously attacked her.

Tough start

Thankfully, Day’s unborn child survived the assault. And just a year after Terrence Jorden was born, his parents went their separate ways. The child’s father would subsequently go on to take his own life in 1967, and allegedly Day didn’t mourn much upon hearing the news.

Second marriage

Then, in 1946 – three years after Day’s split from Jorden – she once again said “I do” to another musician. This time around, it was actress Virginia Weidler’s saxophonist brother, George. Yet this second marriage didn’t last much longer than her first. By the end of the decade, then, the star was once again a single mother.

Secret life

Fortunately, Day seemed to have found “the one” in 1951 when she wed Martin Melcher – a movie producer who also became her manager. Melcher officially adopted Day’s son, too, and the pair seemed to enjoy a happy marriage until Melcher’s untimely death in 1968. But following that loss, Day discovered that her third husband had been hiding quite the secret.

Huge debt

Indeed, unbeknown to Day, Melcher had been spending her hard-earned fortune behind her back throughout their marriage. And the bad news didn’t end there. Not only had Melcher frittered away $20 million during those 17 years together, but he’d also plunged the actress into severe debt as a result. And it seems that both Frank Sinatra and James Garner had long been suspicious about Day’s husband and his habits.

Lawsuit

Naturally, Day decided to try and claw back some of the money that Melcher had squandered, and she did so by suing Jerry Rosenthal. Rosenthal had been a business partner of the actress’ late husband and had also previously served as her own attorney during her second divorce proceedings. And the court ultimately decided in favor of the Hollywood star – although she didn’t see a cent of the compensation that she had been awarded until 1979.

Underhand dealings

Day was also upset to learn that Melcher had signed her up to front her own chat show without her knowledge. In a 1996 interview with OK! magazine, she revealed, “It was awful. I was really, really not very well when [Melcher] passed away, and the thought of going into TV was overpowering... I had also been signed up for a bunch of TV specials – all without anyone ever asking me.”

Controlling

And Day didn’t just suffer financially and professionally at Melcher’s hands. You see, her third husband was also a controlling man who pushed her to constantly work. As a result, then, Day began experiencing problems with her mental health; while shooting Calamity Jane, for example, she battled against panic attacks.

Manson family

Then, a year after Melcher’s passing, Day found herself inadvertently caught up in one of the decade’s most high-profile murder cases. Before ruthlessly killing five people in Los Angeles, Charles Manson’s followers had initially planned to slaughter the actress’ son, Terry. Manson had wanted to get revenge on the music producer following his refusal to work on the cult leader’s album.

Turbulent love life

And Day’s turbulent love life continued when she wed her fourth husband, Barry Comden, in April 1976. The head waiter had wooed the actress by handing out food for her various pets as she left the restaurant at which he worked. But yet again, the marriage didn’t last, and, in 1982, the star became a four-time divorcee. Comden later claimed that his ex-wife had been more interested in looking after animals than him.

Final marriage

So, following the breakdown of that fourth and final marriage, Day dedicated herself to her various animal charity work. She was assisted in those endeavors, too, by Terry. But in 2004 the screen icon was left devastated when the record producer tragically passed away from cancer, aged just 62.

Major loss

This wasn’t the only major loss that Day suffered in her later years, as in 1985 her regular co-star and lifelong friend Hudson had become the first hugely famous face to die from AIDS. The one-time matinee idol had been closeted throughout his career, and his sexuality was only confirmed following his passing.

Loyal friend

Just a year before his death, a visibly ill Hudson had also appeared on Day’s short-lived CBN show. And in Mark Griffin’s biography of the former idol, Day is quoted as saying of that time, “[Rock] was very sick. But I just brushed that off, and I came out and put my arms around him and said, ‘Am I glad to see you.’” The actress was applauded by the gay community, too, for remaining loyal to her friend during an era when fear about AIDS was at an all-time high.

Personal heartbreak

So, Day’s personal life definitely had its fair share of tragedy and heartbreak. But despite her absence from the entertainment world since the turn of the century, the former actress was far from the emotionally scarred hermit that she has often been painted as. In fact, she very much led an active social life right up until her death.

No recluse

Indeed, several of Day’s longtime friends have admitted that they used to find the “recluse” label hilarious, considering how often the star went out. And the actress herself once made it very clear that the media’s portrayal of her was wide of the mark. She’s quoted as saying, “My image, I can assure you, [is] more make-believe than any film part I ever played.”

Frank Sinatra

As Day’s story proves, it was much harder to know the truth about your favorite stars back in the day. Perhaps it’s because they weren’t able to document their lives on social media! But naturally, that didn’t stop the rumors from spreading. Take Frank Sinatra, for instance. By the time he died, fans would have heard their own tales of his alleged affairs, violent temper and mob associations. But how do you separate the fact from the fiction?

True icon

Frank Sinatra was a true icon of the entertainment industry and one of the most successful singers of the 20th century. But out of the spotlight, the man dubbed Ol’ Blue Eyes had a rather colorful private life. And thanks to the star’s apparent associations with dangerous organized crime figures, a long shadow has been cast over his legacy. So, is there any truth to the shocking rumors that dogged Sinatra even before his death?

Gossip

Indeed, some of the gossip surrounding the singer stands in marked contrast to the enduring vision of him as a slick, expensive-suit-wearing crooner. And Sinatra’s music was arguably the soundtrack to an era. In his 1940s and 1950s heyday, he released countless hit singles and chart-topping albums as well as scooping an Academy Award.

Rat Pack

Famously, Sinatra was also the unofficial leader of the “Rat Pack.” Alongside Sammy Davis Jr., Peter Lawford, Joey Bishop and Dean Martin, he bossed Las Vegas’ nightlife scene in the 1960s. And the star’s public image ultimately became that of someone living life to the full. Men wanted to be him, and women wanted to be with him.

Rumors

However, rumors of various kinds would always surround Sinatra. 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.

Daughter?

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.

Another affair

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.

Turned down

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.

Another son?

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.

Farrow remembers

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.”

Sinatra's personality

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.”

Thrower

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.

Bad temper

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.

Frightening incident

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.”

Extensive 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.

Underboss

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.

Huge success

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.

Real mobster

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.

In awe

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.”

Mafia personnel

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.

Documented evidence

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.

Off the record

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.

Bugging his house

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.

Release from prison

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.

Different spots

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.

A misunderstanding

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.

Low point

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.”

Thinly veiled

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.

Mob connections

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.

Labor union

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.

Liaison

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.

Banned from casinos

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.

Mingling

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.

Laissez-faire

“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.

No apologies

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.

Communists

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.

Ransom

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.

Official requests

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.

Insight

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.

Criminal elite

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.