Sinatra's night of passion with Jackie O... and why he boasted she was only his second greatest conquest 

By Adapted From A Book By J Randy Taraborrelli

Published: 19:42 EST, 4 August 2015 | Updated: 20:21 EST, 4 August 2015

Just good friends? Frank Sinatra and former First Lady Jackie Onassis together in 1975

Author J. Randy Taraborrelli thought he knew everything about Frank Sinatra and his women. Then, new confidantes came forward . . . 

In the final extract from his new biography, he reveals the truth about the singer’s stormy final marriage and how he still yearned for Ava Gardner. 

The bride was former Las Vegas showgirl Barbara Marx, who looked stunning in clouds of beige chiffon. But there was a certain imperiousness in the way she held herself that grated on one of the guests.

It wasn’t that Nancy Sinatra minded her father taking a fourth wife. It was just that, in her gut, she knew this marriage spelled trouble.

Given that it had taken four long years to get Sinatra to the altar, Barbara was entitled to feel triumphant.

Since the early days of their relationship, she’d decided to mould herself to his life — staying up with him until the early hours, dancing every night if required and even drinking more than usual.

She’d even left her husband Zeppo Marx (the unfunny member of the Marx Brothers), before she had a place to call her own. But when she told Sinatra she’d love to buy a particular small house, but probably couldn’t afford it, he’d bought it for her the next day with cash.

Some people felt she’d manipulated him, but Barbara was never one to worry about wicked whispers. Her romance with the singer, however, wasn’t all sweetness and light. There was Sinatra’s violent temper to contend with, for a start.

One day, for instance, after Barbara was served a piece of under-cooked veal, he’d yelled at his personal chef and given him a total of five seconds to leave the house.

Sinatra could also be crude or mean, and Barbara was sometimes his target. Once, at a restaurant in New York, she’d tried to contribute to a conversation he was having with his pals about politics.

Sinatra, who’d a few cocktails, laid into her. ‘What the hell are you talking about?’ he shouted. ‘You don’t got no opinion here. You just sit there. If I want to know what you think, I’ll ask you. Until then, you just sit there and keep your mouth shut.’

Barbara did what she was told. She’d long since learned that small battles didn’t matter as long as she won the big ones.

When she accompanied him on singing tours, his staff noticed, Sinatra was in a good mood almost every day. There was nothing he wouldn’t do for Barbara then, no gift he wouldn’t buy her.

Before long, she’d left her little house and was living with him at his compound in Palm Springs. But the relationship began to falter in 1975, largely because she wanted marriage and he was ambivalent.

Sinatra in an earlier meeting with the then Jackie Kennedy in 1960. Years later they had a dinner date and apparently ended up back at his hotel suite at the Waldorf Towers

They agreed to have a trial separation — and it was at this point that Sinatra had a well- publicised dinner date with Jackie Kennedy Onassis in New York.

Later, they apparently ended up in his hotel suite at the Waldorf Towers, where they spent the night together — or at least that’s what Frank suggested to his buddies.

One of them, Jim Whiting, recalled Sinatra once being asked by his friends who had been the biggest conquests in his life.

‘Sinatra said that on top of the list was Ava [Gardner], then Jackie, Lana [Turner] and Marilyn [Monroe]. Everyone said: “Wait a second! Jackie? What, are you kidding me?” Sinatra got real quiet and said: “I ain’t talkin’ ’bout that.” ’

Another Sinatra buddy, Tony Oppedisano, said he remembered the singer making it clear ‘there were feelings there’. Barbara, meanwhile, was alarmed when she saw Press photos of her lover with Jackie. So she called him — and they ended up talking for hours. The upshot was that Sinatra agreed to give their relationship a serious chance.

Ava Gardner and Frank Sinatra seen boarding a plane in 1951

Jackie Onassis leaves Jilly's in New York after attending a Sinatra comeback concert.  Sinatra said she was second on his list of top conquests

That meant he first had to clear the decks — so he gave two young actresses he’d also been seeing their marching orders. But then he started thinking about the woman who’d been his greatest passion — Ava Gardner.

It was almost 20 years since they’d divorced, but he started calling her regularly at her home in Italy. Though they never met in person, they soon found themselves falling in love all over again.

Sinatra asked Ava, then 54, to marry him again — and she convinced herself it was a good idea. Taking her maid with her, she went out to buy a wedding trousseau — including a wide array of nighties and negligees.

Sinatra on his wedding day to his fourth wife Barbara Marx, a former Las Vegas showgirl

But a few days later, Ava came to her senses. Calling Frank, she told him it was over as far as she was concerned, and he should go ahead and marry Barbara instead. ‘I guess I’m stuck with Barbara,’ Frank told his pals Jilly Rizzo and Jim Whiting over drinks at his house.

‘It’s not the future I wanted, but maybe it’s the one I deserve.’

He seemed less like a man in love than a man resigned to his fate.

Aware that his family wouldn’t be ecstatic about his engagement, Sinatra dispatched his lawyer, Mickey Rudin, to tell his mother Dolly — a former back-street abortionist from New Jersey.

Rudin said his ears smarted for days from the language Dolly had used in response to the ‘good news’. The wedding ceremony was nearly cancelled on the day. As Barbara was getting ready, Rudin suddenly handed her a pre-nuptial contract.

As Barbara tells it, she was surprised, because Sinatra had never mentioned a pre-nup. She refused to sign — until told in no uncertain terms that the wedding would be cancelled.

But did this really happen the way she recalled it? A document — signed by her and dated three days before the wedding — confirms she’d hired her own lawyer to negotiate the terms of the pre-nup.

To be fair on Barbara, there seems no doubt that she was genuinely in love — and that Sinatra loved her in return. But his daughters still felt uneasy. Matters came to a head after Sinatra’s mother died in a plane crash.

The day after the funeral, Barbara swooped on Dolly’s house, removed furs, jewels and other valuables and locked them in an enormous closet in her bedroom. As she explained later, she wanted to keep them safe until other family members could sort through them.

Tina and Nancy didn’t know this, and were astonished to find their grandmother’s belongings gone.

Sinatra knew better than to take sides. He simply asked Tina and Nancy, then aged 29 and 37, to pick what they wanted.

This was fine with Barbara. But when Nancy and Tina began sorting through the valuables, they claimed a good many things were missing — jewels, furs and other costly items.

‘[Barbara] had been “protecting” Dad’s interests,’ Tina would note later. ‘But from who? The answer was obvious and disturbing. [She] was protecting my father from the people she perceived as her stiffest remaining competition. His children.’

If the children were alarmed, so, too, was their mother when she learned of Barbara’s desire to have another wedding in 1978 — this time in church. As they were both Catholics the only way this could happen was if his previous church wedding was annulled. Not surprisingly, Nancy senior refused.

Sinatra with his wife Barbara, left, and hos mother Dolly, right. The day after Dolly's funeral, Barbara swooped on her house, removed furs, jewels and other valuables and locked them in an enormous closet in her bedroom

‘You don’t annul a marriage that happened 40 years ago and produced three grown children,’ Sinatra’s priest, Father Rooney, told him.

‘Yeah, you do, if you want to bad enough,’ was Frank’s response.

Sure enough, the marriage to Nancy was annulled — though to this day, no one knows how it was achieved. And Barbara got her church wedding.

Once again, the daughters were very upset. Tina berated her father, telling him the annulment was not only hurtful to her mother but implied his children were illegitimate.

By the beginning of 1985, Barbara and Sinatra were having serious conflicts of their own. Her main point of contention was that he was losing too much of his hard-earned money by gambling and giving extravagant gifts to his children.

The children were old enough to fend for themselves, she said, and shouldn’t be accepting gifts worth thousands from their father.

The Sinatras, however, felt she was really just trying to control their father’s finances.

The presents stopped, but not — Nancy noted — the gifts to Barbara. By then, Sinatra had bought her so much expensive jewellery that it filled a steel strongbox 2ft long, 1ft wide and 8in deep.

But even these gifts stopped after Barbara criticised one of his uncouth drinking buddies.

By the beginning of 1985, Barbara and Sinatra were having serious conflicts of their own. Her main point of contention was that he was losing too much of his hard-earned money by gambling and giving extravagant gifts to his children

‘You know what? You’re outta here,’ Sinatra told her. ‘Pack your bags, every one of ’em. Damn it!’ he exclaimed as he raised his fists. ‘I want to punch you so bad right now, you don’t know how bad.’ Barbara left him two weeks later. But Sinatra, about to turn 70, missed his wife.

He also found the prospect of a divorce battle less than appealing — and knew she’d hired an expensive lawyer.

A month later, the couple were back together and it wasn’t long before Barbara was asserting herself more than ever. She decided to have her pre-nup rescinded and Sinatra signed the necessary legal documents.

Under the new agreement, all the money he’d earned during his fourth marriage — along with any future income — would be considered half hers.

On top of that, her personal legal team tried to stop Sinatra paying alimony to Nancy senior — which he’d been doing for 40 years. They even asked for past payments to be reimbursed — but failed on both counts.

By the time Nancy’s daughters were left off the guest list for Frank’s 80th birthday dinner, relations between them and their stepmother Barbara were at an all-time low.

Then something happened that changed everything: in November 1996, Frank had a heart attack.

He was rushed to Cedars-Sinai hospital in Los Angeles, and was found also to have pneumonia in his left lung. When Tina got the call, she had to be with her father. The bad blood between her and Barbara no longer mattered.

Sinatra was in hospital for eight days. On the afternoon of his release, Barbara called Tina, Nancy and their brother Frankie out into the hallway.

Taking Tina’s hands into hers, she said: ‘I just want all three of you to know that anytime you want to visit your father, you are more than welcome to come by the house. Day or night.’

She seemed sincere. ‘Oh my God, Barbara,’ Tina said. ‘I’ve waited so long to hear you say that.’

During his final years, Sinatra suffered from cancer, kidney problems, bladder ailments and mini-strokes. His three children spent more time than ever with him, and Barbara welcomed them with open arms.

The end, when it came, was sudden. On May 14, 1998, Barbara had gone out to dinner, leaving Sinatra in the care of staff, when he had to be rushed to hospital. Frank died shortly after she arrived. He was 82.

Everyone, including Barbara, was left well-provided for in Sinatra’s will. At his funeral, however, I failed to observe any signs of closeness between his daughters and his widow.

• Adapted by Corinna Honan from Sinatra: Behind The Legend by J. Randy Taraborrelli, published by Sidgwick & Jackson on August 13 at £20. © J. Randy Taraborrelli 2015. To pre-order a copy for £16, visit mailbookshop.co.uk or call 0808 272 0808. Offer until August 8, P&P is free.

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