Inside Tony Bennett’s tumultuous love life – from two failed marriages rocked by drugs and infidelity to his decades-long relationship with third wife 40 YEARS his junior who he ‘met’ when her pregnant mom went to his concert

• The musical legend was married three times across his decades-long career
• The singer’s first marriage was torn apart by accusations of infidelity 
• He met his current wife, Susan, when she was only 19 and he was 59 
• READ MORE – Tony Bennett’s life in pictures: The timeless crooner who defined an era as he dies at 96

Tony Bennett famously crooned that he ‘left his heart in San Francisco’ – but in reality, the legendary musician actually handed his heart over to several women throughout his life on his quest to find a love that was as epic as the romances he sang about. 

While Bennett, who passed away on Friday at the age of 96, wooed the world with his silky smooth voice, his personal life was far more rough – with the singer going through multiple failed marriages, explosive allegations of infidelity, and scandalous affairs with women who were decades younger than him. 

In the end, Bennett’s love life seemingly brought to life the ‘Rags to Riches’ lyrics that he was best known for – with the singer finally finding happiness and stability with his third wife, Susan Benedetto, who cared for him in his final days before his death. 

But even his picture-perfect romance with Susan was not without its scandal – not least because of the 40-year age gap between the pair.

Tony Bennett has passed away at age 96. He’s been married to a woman named Susan Benedetto (seen in 2007) for decades, but his road to discovering true love was rocky

The musical legend was married three times over his decades-long career. He’s seen with his second wife, Sandra Grant, in 1980

Decades before he met Susan, Bennett first tied the knot in 1952 with a 19-year-old art student named Patricia Beech, after he saw her in the crowd at one of his shows and became instantly drawn to her.

Unfortunately, it seemed as though the couple was doomed from the start, since news that Tony – who was at the height of his career – was getting married did not go over well with the public. Roughly 2,000 of his female fans actually showed up to boycott the wedding, wearing all black to symbolize that they were in mourning.

And as Tony continued to propel into mega-stardom, the immense fame and constant traveling soon put a major strain on their relationship.

It didn’t help that women were often throwing themselves at the heartthrob, and his first marriage quickly came crumbling down amid rumors that he had struck up an affair with actress Sandra Grant.

As the world comes to grips with the tragic loss, FEMAIL went ahead and recapped his rollercoaster ride love life – which was filled with multiple failed marriages, explosive allegations of infidelity, and controversial affairs with women decades younger than him 

He and Sandra went on to tie the knot in 1971 – marrying almost immediately after his first divorce was finalized – but the artist’s life took a dark turn soon after.

Coming off the high of being one of the most well-known faces on the planet, Tony was in for a shock when his career suddenly plummeted amid the introduction of the Beatles in America and the public’s dwindling interest in jazz music.

As he struggled to come to grips with the realization that ‘people didn’t want to hear’ his music anymore, he turned to drugs and alcohol – developing a severe cocaine addiction that nearly took his life.

But Sandra stuck by his side through his rampant partying and almost-fatal drug use, but the two ended up going their separate ways years later. 

It’s unclear what lead to the split, but one thing that is clear is that it didn’t end amicably because she later branded the star as an ‘old fool’ who was very different from the ‘Mr. Nice Guy’ that the public perceives him to be.

Tony started dating his third wife, Susan Benedetto, in the ’80s, and while she ultimately proved to be his true love, that relationship was just as controversial as the others.

Not only was the award-winning musician 40 years her senior, but the two got together when she was only 19 and he was 59 – they met when she was president of his fan club after she had sent him a letter begging for a chance to come back stage and take a photo together.

Another eye-brow raising development came when Tony later revealed that he actually crossed paths with Susan years prior – when she was in her mother’s womb. It turns out, he met her mom at a show when she was pregnant in the ’60s, unknowing that the daughter in her stomach would one day become his wife.

Even so, Tony and Susan have stood the test of time, and were together for more than four decades – up until he passed away on Friday. His cause of death has not been revealed, but he has battled Alzheimer’s for seven years.

As the world comes to grips with the tragic loss, FEMAIL went ahead and recapped his rollercoaster ride love life – which, despite the cheating accusations and messy splits, ultimately had a happy ending thanks to Susan.

Tony married his first wife, a 19-year-old student named Patricia, after he noticed her in the audience at his show – and 2,000 of his female fans tried to boycott the wedding by showing up in all black

Tony met his first wife, an art student and part-time model named Patricia Beech, at a nightclub in Ohio. They wed in February 1952 – when she was only 19 years old and he was 26

Tony met his first wife, an art student and part-time model named Patricia, at a nightclub in Cleveland, Ohio. 

He later explained in his 1998 memoir, The Good Life, that he was performing when he spotted her in the audience, and was instantly drawn to her.

‘I could see her from the stage – she was sitting ringside – and I was taken with her beauty,’ he recalled.

They went on their first date the next day, and the two became boyfriend and girlfriend soon after.

They wed in February 1952 – when she was only 19 years old and he was 26 – but their union sparked a harsh reaction from his most dedicated supporters.

At the time, Tony was at the height of his career, and many of his female admirers were fiercely disappointed that the heartthrob was tying the knot.

The couple went on to welcome two sons together, Danny in 1954 and Dae in 1955. Unfortunately, they split in 1969 amid rumors that he was unfaithful. They’re seen in 1954

Roughly 2,000 of his fans gathered outside St. Patrick’s Cathedral in Manhattan where he and Patricia got married, wearing all black to represent being in mourning over the fact that their chances of being with Tony had diminished.

Even so, the public’s dismay did not put a damper on their romance, and the couple went on to welcome two sons together, Danny in 1954 and Dae in 1955.

Unfortunately, his busy tour schedule negatively impacted their relationship – she was forced to stay home and take care of their two young kids while he traveled the world – and by the late ’60s, it had become strained.

‘The long separations when I left home to play the clubs killed [my] marriage,’ he once explained. ‘I had to go on the road. But for a marriage to work, both parties have to be there.’

All the while, Tony was growing close to his next wife, aspiring actress Sandra, which was the final straw for Patricia.

While he did not admit to cheating on Patricia, he hinted that he was unfaithful in his book, recalling one night when he and Sandra were alone together in a hotel room when Patricia caught them.

‘Patricia called and Sandra answered the phone. We were officially separated from that moment on,’ he said. 

She filed for divorced in 1969, and it was finalized two years later, in 1971.

The musician’s second wife, Sandra, was by his side when his career started to crumble and he developed a severe drug addiction – and she saved his life after he overdosed in a bathtub

Almost immediately after he and Patricia went their separate ways, Tony started dating Sandra, who was 14 years his junior. They’re seen in 1968

Almost immediately after he and Patricia went their separate ways, Tony started dating Sandra, who was 14 years his junior.

The two met at a pool party at the Beverly Hills Hotel in 1965, and she became pregnant with his third child in 1970, while he was in the midst of divorcing his first wife.

The two met at a pool party at the Beverly Hills Hotel in 1965, and they quietly tied the knot as soon as he was legally separated from Patricia in 1971. They’re seen in 1972

His daughter, Joanna, was born later that year, and he and Sandra quietly tied the knot as soon as he was legally separated from Patricia in 1971. They then welcomed another daughter, named Antonia, in 1974.

However, in the late ’70s, Tony’s life took a dark turn. Despite being one of the biggest stars on the globe throughout the ’60s, his career started to crumble as he struggled to write hits.

He eventually lost his manager, followed by his record label, and turned to drugs and alcohol.

The musician developed a severe cocaine addiction that nearly took his life, but it was his wife Sandra that ultimately saved him.

The National Enquirer reported that she found the acclaimed singer after he had overdosed in a bathtub in 1979, and revived him ‘in the nick of time.’

She gave birth to his daughter, Joanna, in 1970, and they then welcomed another daughter, named Antonia, in 1974. He and Sandra are seen with Joanna in 1971

Sandra reportedly saved Tony’s life after she found him after he overdosed in a bathtub in 1979, and revived him ‘in the nick of time.’ They’re seen with their daughter in 1971, a few years prior

Tony told the outlet that nearly losing his life was an eye opener and he ‘just stopped’ doing the drugs cold turkey after that. 

‘I had to because I thought I was going to lose everything,’ he explained. ‘I’ve been given this gift. I know how to sing and perform. I was sinning against this gift. I thought, “I’m not going to do this anymore.”‘

After that, Tony called his eldest son, Danny, and asked them for help. He said, ‘Look, I’m lost here. It seems like people don’t want to hear the music I make,’ Danny later recalled to AARP. 

Danny became his manager and Tony made a major comeback in the late ’80s and ’90s. 

While Sandra stuck by Tony through his imprudent partying and drug use, the two went their separate ways in 1983, after 12 years of marriage.

While Sandra stuck by Tony through his imprudent partying and drug use, the two went their separate ways in 1983, after 12 years of marriage. They’re seen in 1973

It seems it didn’t end amicably because she later branded the star as an ‘old fool’ who was very different from the ‘Mr. Nice Guy’ that the public perceives him to be

The pair kept many details of their whirlwind romance and eventual split out of the public eye, so it’s not known what lead to their divorce.

But Sandra did shed a little light into what went down when she spoke to Page Six about it years later.

She made it clear that things didn’t end well for them – and she completely slammed her ex in the scathing interview.

She explained that it took more than two decades for their divorce to finally be finalized – she said it was finalized in 2007, but didn’t divulge why it had taken so long – and at the time, she told the outlet that she was ‘so happy to be free at last’ and branded Tony as an ‘old fool.’

‘Thank God my divorce papers are finalized with Tony after all these years,’ she said. ‘The Tony I knew is not the same smiley Mr. Nice Guy the world knows. 

‘He is not much of a gentleman. I married the wrong man. I am very happy to be free at last, and good luck to his current wife.

‘But maybe it’s the opposite and I should wish him luck. There’s no fool like an old fool. I have very little feeling for him anymore.’

The singer first crossed wives with his third wife, Susan, when he was 40 years old and she was in her mother’s womb – and they started dating years later while she was the head of his fan club

Tony started dating his third wife, a school teacher named Susan (seen in 1999), in the late 1980s, and their relationship raised a lot of eyebrows since he was 40 years older than her

Tony started dating his third wife, a school teacher named Susan, in the late 1980s, and their relationship raised a lot of eyebrows due to their immense age gap – the musician was 40 years older than the educator.

In addition, they had a very controversial first encounter. They actually crossed paths for the first time when she was in her mother’s womb.

Susan’s mom, Marion Crow, was a big fan of Tony’s and met him at a show when she was pregnant – unknowing that the daughter in her stomach would one day go on to become his wife.

Tony opened up about the odd connection in his 2016 book, Just Getting Started, explaining that he posed for a photo with Susan’s mom backstage at his New York City concert in 1966.

‘As fate would have it, Marion was pregnant at the time with… Susan,’ he wrote. ‘It’s a photo we all laugh about knowing the incredible turn of events that followed.’

Since Susan’s parents were huge fans, they played all his songs for her as she grew up, and she went on to become president of the singer’s San Francisco Bay Area fan club as a teenager.

They met when she was 19 and he was 59 – she was president of his fan club after she had sent him a letter begging for a chance to come back stage and take a photo together

They went on to tie the knot in 2007, and were together up until his passing this week. They’re seen together in 2003

Then, when she was 19 and he was 59, they met again – and this time, it lead to their romantic connection. 

‘When she was 19 she had tickets to see me perform at the Masonic Temple in San Francisco and she put in a request to say hello backstage after the show, probably not expecting a response,’ he wrote.

‘The request was sent to me, and it tickled me that someone of her age was so devoted to my music.

‘I not only agreed to say hello to her backstage, but asked her to be my date for the evening, and that’s how it really all began … foreshadowed by a backstage photo taken in 1966.’

They went on to tie the knot in 2007, and were together up until his passing this week.

Together they co-founded Exploring The Arts, an arts education charity, as well as the Frank Sinatra School Of The Arts in his hometown of Queens, New York.

‘Susan Benedetto has shown me how love gives you the confidence and courage to be your best self, and the inner peace and contentment that come with them,’ he gushed of his wife in his book.

In 2021, after it was revealed that Tony was suffering from Alzheimer’s, Susan opened up about the difficulties of seeing her husband deteriorate.

‘There’s a lot about him that I miss, because he’s not the old Tony anymore. But when he sings, he’s the old Tony,’ she said.

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