The Many Loves of Frank Sinatra

You need only say “Frank”  – millions connect at once to the second name. Sinatra. His music is an evening dress slipping down to reveal a soft shoulder. A hand sliding up a thigh, probing for the stocking top. Sinatra would be 100 years old in December, but his songs remain part of the background of all our lives. In a world where celebrity lasts but a nanosecond, Frank Sinatra holds his value.

One day, soon after Sinatra’s death, a New York editor took us to lunch.  He asked us to write Frank’s biography. One that would square the circle between the great artist and the monster that seemed to lurk behind the headlines. The editor wanted it all – the music of course, but also the truth about the Mafia connection and the notorious temper. And the women.

Frank couldn’t read music and wrote only two songs – his talent lay in the seductive skill he brought to the material. When Sinatra sang of longing, of love found and lost, the listener knew he’d been there himself.

Frank’s women were a special challenge.  There were (really were) so many of them – press clippings hinted at affairs with starlets, songbirds and society girls too numerous to count – and habitual use of prostitutes. Oh, and four wives. Most of the information came from gossip columns – unnamed sources, friends of friends. While he was alive Frank’s real friends obeyed his edict: “Don’t tell!” Now that he was dead we set out to break through the wall of silence. Hundreds of interviews later, here is the story.

The young Sinatra and his parents, like other working class Italian-Americans of the nineteen-thirties, escaped in summer to the New Jersey shore. In 1931, at 15, Frank crossed the street to chat up a pretty girl named Nancy Barbato. He had a concave chest, a still reedy voice and a ukulele under his arm. “I was a poor, lonely, and discouraged kid, when I met her,” he said later. “In Nancy, I found beauty, warmth and understanding.”

That didn’t stop Frank straying. “There were lots of women,” his old friend Lucille Buccini told me. “His ears stuck out,” another pal recalled, “but broads swarmed over him.” Frank told his friend Tom Raskin, “I’m just looking to make it with as many women as I can.”

That youthful ambition rapidly got him into trouble. One girl, another Nancy, feared she’d become pregnant after a night with Frank. She remembers dragging him to church, where he prayed “C’mon God, gimme a break, will ya?” God obliged – on that occasion.

An infamous mugshot of Sinatra, prisoner number 42799, dates from 1938. Taken only weeks before Frank and Nancy’s wedding, it relates to an amatory misadventure with a woman named Toni. “He was promising both women that he’d marry them,” remembered Fred Travelena, who worked at the club where Frank had started singing.

Lucille Buccini was there the night Toni stormed in to confront Frank – in front of Nancy. Toni filed a complaint against him with the police. The charge? “Seduction…of a single female of good repute for chastity, whereby she became pregnant.” Toni wasn’t pregnant and was already married to another man.

Frank and Nancy got married soon after. She worked days (and had babies), while Frank worked nights singing in the clubs. In 1940, when he got his break with the Tommy Dorsey band and went to Hollywood, Frank indulged “his first big love away from home.”  He and a young actress named Alora Gooding holed up in a rented penthouse. More than fifty years later, Gooding’s daughter Julie would claim Frank as her father.

Back in Hollywood in 1944, by now a national sensation with a movie contract from MGM, he brought Nancy – and their daughter and infant son – with him. That did not deter him from drawing up a shopping list of actresses he’d like to bed – and working through it. Frank’s relationship with Nancy had been “neighbourhood serious,” as pianist Joe Bushkin put it. But Frank had left the neighbourhood.

A home movie shows Sinatra by a pool, holding a lit cigarette between his toes. As a blonde enters the frame, the two exchange looks and banter. Singer Marilyn Maxwell, billed as “one of the best sweater-fillers in Hollywood,” had known Frank since they were both young band singers and they had a passionate affair. “Crazy about each other,” Frank’s pal Nick Sevano recalled.

Frank certainly took crazy risks. At a New Year’s party in their own home Nancy spotted a diamond bracelet glittering on Maxwell’s wrist – identical to one she had seen in the glove box of the family car days before and imagined was for her. Frank promised to end the affair.

The marriage wobbled on. Frank started going out on his own and drinking too much of  the Jack Daniels he would make famous. Nancy – who still reminded her husband to wear his galoshes when he went out in the rain –  must have seemed like a clucking hen compared to the brilliantly plumed birds of Hollywood. Marlene Dietrich and Lana Turner were among the more exotic creatures Frank bedded.

At forty-four, Dietrich was fourteen years Sinatra’s senior, her husky voice long since internationally famous. Her many lovers had included Maurice Chevalier, Jimmy Stewart, John Wayne – and some women, including Greta Garbo.

“I know they had a thing going,” said Frank’s songwriter Sammy Cahn, “She had powers as a lover that were spoken of behind people’s hands …she was supposedly the champion in the oral sex department.” Marlene herself described Frank as “the only really tender man I have ever known.”

MGM’s leading sweater girl, Lana Turner, was in 1946 preparing for her role as an adulteress in The Postman Always Rings Twice – the first movie version. When they began an intense affair, too blatantly, Nancy issued a public statement saying Frank had left home “seeking the freedom of separation without divorce.”

Hollywood contracts in those days routinely included a “morals clause,” and a tearful Lana was soon denying the affair. “I have never in my life broken up a home,” she told reporters. Within three weeks of leaving, Frank sang “Goin Home” to Nancy in a nightclub, and did just that.

Even as he dallied with Lana, Frank had been romancing a bit-part actress named Shirley Ballard. “We were in Palm Springs, at the Chi Chi Club,” she told me. “Frank tips back in the chair and eyeballs me and sings ‘I’ve Got a Crush on You’ – to me! Those blue eyes. They nailed you.” At his latest penthouse hideaway, Frank introduced her to the intricacies of music – classical music – and got her into bed. He was a “considerate lover, not selfish,” as she remembered it.

Shirley also saw another side of Frank. He cheerfully took her to the house where the mobster Bugsy Siegel had been riddled with bullets, to toast his departed friend in champagne.

The Sinatra marriage was now so damaged that in 1947, when Nancy again found herself pregnant, she went off to Mexico for an abortion. Frank was devastated. Though they went on to have a third child, the marriage was beyond repair.

Enter Ava Gardner, the woman who was to be Frank’s femme fatale. She was a tough-talking, hard-drinking, volatile actress from Nowhereville who had been married and divorced twice – and her star was rising at a time Frank’s was in decline. “My God, she was beautiful!” her friend Peggy Maley remembered. In those pre-email days, the two women came home each night to an avalanche of handwritten invitations from suitors. Even as headlines began to ask “Is Sinatra Finished?,” he set out to win her.

When they went to bed, Ava remembered, she “truly felt that no matter what happened we would always be in love.” When the press found out  Nancy, “terribly hurt,” started divorce proceedings at last.

Ava had been right. She and Frank would be in love for the rest of their lives. They both drank, though, and fought constantly. When Ava dallied with a co-star, Frank retaliated with infidelities of his own. One night he took an overdose of sleeping pills. “He suffered,” Sinatra’s friend Brad Dexter told us. “Ava emasculated him.”

Frank married Ava all the same, but soon she was complaining that he was an absentee husband and went to bed with the director of her latest film. She claimed that she aspired to motherhood, and twice became pregnant during the filming in Africa of Mogambo. Each time, she took off for London to have an abortion. When she told Frank of the first abortion, after the fact, he sobbed uncontrollably. The second child was likely fathered not by Frank, but by an adviser on the Mogambo shoot, a very English “great white hunter.”

“The exact moment I made the decision to seek a divorce,” Ava said years later, “was the day the phone rang and Frank was on the other end announcing that he was in bed with another woman.” In autumn 1953, after a publicist announced the couple’s separation. Frank slit his wrists. He survived, of course, as he did other half-serious suicide attempts.

Professional and personal oblivion threatened, but Frank fought his way back .  There was the Oscar-winning performance as Maggio in the movie From Here to Eternity.  Then there was his triumph with the albums that would become the core of his legacy: Songs for Young Lovers, Swing Easy, In the Wee Small Hours and Only the Lonely. And on and on.

The personal life, though, remained a sad struggle. The night he won the Oscar, Frank wandered Beverly Hills alone, clutching the little gold statuette. He sometimes took visitors “home” to Nancy and the children – the neighbourhood girl still kept a few of his shirts in the cupboard, his monogrammed towels in the bath.

“It was nightmare time after Ava,” one of Frank’s lovers recalled. Those briefly enlisted to banish the bad dreams included Anita Ekberg and the heiress Gloria Vanderbilt.  Vanderbilt, who had a husband forty-two years her senior, wrote that she could “not imagine a long tomorrow with F. and me in it.” Jeanne Carmen, a pin-up girl and trick golfer who dated him off and on for years, remembered him above all as having been “needy…like a little boy.”

Nineteen-year-old singer Jill Corey noticed Frank watching her as she performed in a club in Manhattan. In 2001, she quietly sang me the song she’d written about their first date, the start of a five-year relationship.

“Tonight I’ve a date with Sinatra,

Oh God, I’m experiencing angst!

In my virginal state, should he kiss me I’d faint,

And do I call him Frankie or Frank?”

There were few virgins. On a tour of Australia, his fourteen-year-old daughter Nancy was horrified to find a pair of women’s stockings in her father’s bedroom. Frank’s valet George Jacobs said his boss leafed through movie magazines looking for women to “do”. He rushed at women, then dumped them. “All of a sudden,” sighed one conquest, “he doesn’t phone.”  Frank had abandoned Jill Corey in favour of a game of cards.  Ava haunted him. “I will never hurt like that again,” he told his daughter Tina.

Frank’s home was still a shrine to Ava, photographs of her were everywhere. For a couple of years in the mid-fifties, he appeared to be serious about the jazz singer Peggy Connelly. She looked very like Ava. Frank was an “energetic and interested” lover, Connelly told us, “but it was more about himself.” Though intelligent and hugely generous, he had an explosive temper. “If he got angry, it went from zero to ten,” Peggy said. “There wasn’t much in between.”

Peggy once returned from a trip to find that Frank had spent the night – in the hotel room they shared – with Ava.  He twice asked Peggy to marry him, but she turned him down. She was not about to tolerate relapses into the arms of Ava, and left Frank for good in 1957.

Frank again moved on. Some think his affair with Lauren “Betty” Bacall, the famously devoted wife of Frank’s close friend Humphrey Bogart, started even before Bogie died from throat cancer. “There must have always been a special feeling alive between Frank and me,” Bacall wrote later. At Christmas 1957, months after his most recent proposal to Peggy Connelly, Frank asked Betty to marry him. Then he broke with her, accusing Bacall of leaking the news of the engagement to the press. Betty said later “I couldn’t have lived with that fucking mercurial personality” anyway.

Frank had power, and power usually ensured his lovers’ silence. Decades passed before Zsa Zsa Gabor revealed that Frank cajoled her into having sex – with her child sleeping just along the corridor – by refusing to leave until she relented. Sandra Giles, another actress, fell asleep drunk at Frank’s house and woke to find herself in bed  – undressed now  –  and Frank trying to badger her into sex by claiming they’d made love earlier. It was a lie. The husband of Shirley Van Dyke,a would-be actress, told us of a sordid deal.  In return for sex, he claimed, Sinatra got Van Dyke acting jobs.

Early in his time with Bacall, Frank had a fling on the side with Hungarian actress Eva Bartok. Nine months later, when she gave birth to a baby girl, she left blank the space for “Father’s Name” on the birth certificate.  She always felt “1,000%” sure, however, that the child was Frank’s.  The little girl, Deana, looked like him, down to those magical blue eyes. Eva, and eventually Deanna herself, years later wrote to Frank begging him to acknowledge his daughter. They wanted nothing of him, they emphasized, except the chance to meet. Frank replied, through his lawyer, that he was too busy.

In the Rat Pack period of the early 1960s, by then in his mid-forties, Frank was still flailing around for love. There was the dark-haired beauty Judith Campbell, whom Frank first bedded and then handed over to John F. Kennedy. Witnesses we interviewed said Campbell took money for sex – something she long denied – and may have been put in Kennedy’s path by Sam Giancana, one of Sinatra’s powerful Mafia cronies.

Marilyn Monroe also served Sinatra and Kennedy as on-off lover. Dean Martin’s wife Jeanne remembered a cruise in the summer of 1961, when Marilyn and Frank shared a cabin. “She was half dressed,” Martin recalled, “wandering around the deck…pitifully trying to find someone to give her pills at three o’clock in the morning.”

Frank soon announced his engagement to the twenty-three-year old dancer Juliet Prowse, whom he’d met on a movie set.  They set up house together. Frank painted, while Juliet tended the garden. But he wanted her to stop working, got drunk and flew into violent rages – bang went another relationship.

In 1964, when Sinatra took up with nineteen-year-old Mia Farrow, she saw in him a “wounding tenderness that even he can’t bear to acknowledge.” They married in a four-minute Las Vegas ceremony two years later. Photographs show her in evening dress, looking childlike among Frank’s much older friends. As with Prowse, the terminal rift came over Mia’s career. She insisted on honouring her contract to finish work on Rosemary’s Baby, and Frank despatched a lawyer with divorce papers.

After what was supposed to be his “retirement” in 1971, Frank turned sixty-six. He still dated, but half-heartedly now. “We slept in the same bed,” actress Patty Duke said, “but never was there any sex.”  With Marianna Case, a Playboy-bunny he’d noticed in a bra commercial, things never went beyond a “kiss and a hug.” Frank’s daughter Tina thought him the loneliest man in the world.

What he looked for in a woman now, he said, was intelligence and a degree of reserve. He seemed for a while to have found her in Lois Nettleton, a sensitive stage actress who for once was only fifteen years his junior. They listened to classical music, cycled together on quiet roads in Palm Springs. He gave Lois little gifts, called her “scrumptious”. Then suddenly, out of nowhere, he turned on her in a rage over nothing and stormed off. Another goodbye.

Frank could neither really retire nor live for long without a woman at his side. In 1974, when he returned to the microphone and delighted the Madison Square Garden audience with “Let Me Try Again,” the lyrics seemed especially appropriate. He had embarked on a relationship that would last.

It had looked briefly as though Frank would circle back to first wife Nancy. Twenty-five years after divorcing, they spent a few tender days together. Frank spoke of reconciliation, if not with Nancy then perhaps – for he never gave up – with Ava. Frank’s daughter Tina thought the new woman he’d been seeing lately, former showgirl Barbara Marx, was just “a one-night stand with an extended visa.”

Wrong. When Frank did call Ava several times asking if she would come back –her companion Reenie Jordan remembered – Ava “told him no. She told him to marry Barbara.” And so he did, and they stayed together until his death at eighty-two. He called Barbara “the sunshine of my life.” Tina Sinatra, especially, loathed her, thought she was only after Frank’s money. The last Mrs. Sinatra does not give interviews.

The love of Frank’s life had been Ava. When she died years before him, of drink and cigarettes, a distraught Sinatra went on stage and sang the lament that – for him – was about the woman he could not forget:

“I could tell you a lot

But you gotta be true to your code

So make it one for my baby

And one more for the road.

He never did tell, never wrote an autobiography. He sang the songs the lonely heart sings, and sings them still.

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