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Australian man who won lottery five times has "been to hell and back"

May 11, 2021, 2:49 pm

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After the Big Win

Unfortunate winner has had a tumultuous time since landing his windfall

By Kate Northrop

An Australian man who won the lottery five times revealed that his life has been anything but glamorous.

Carlo Massetti, 47 and a Kiwi living in Sydney, Australia, flew back to his native New Zealand to heal and cope with the tumultuous events that have defined his life since winning millions.

The unlucky lottery winner is out to prove that happiness and love can't be bought or won. On the contrary, he's "been to hell and back," having been charged with domestic violence after a five-year relationship turned "toxic," spent time in prison, was targeted and assaulted by inmates, and suffered with mental illness. To boot, he supposedly lost all his lottery winnings.

Five years ago in Queensland, Massetti met Danielle Prebble, 30, a sales manager at an agency that handled celebrities. The two both claimed to be in an unhappy marriage, and having had an instant connection, they entered a "wild affair" and moved in together in Bondi.

"We saw each other three times and began to develop strong feelings," Massetti told the New Zealand Herald. "Some of my friends have said, 'Carlo, you need your head read. She is using you. She's after your money and wants a free ride.'"

However, the pair met long before before Massetti landed millions in 2018.

"I am not a fool and that was not the case with Danni," Massetti stressed.

The former funeral director won two smaller prizes in 2012, but he struck gold when he won three major prizes in 2018. On May 7, 2018, he won AUS$1 million (US$783,000). Just five days later, he took home an AUS$1.47 million (US$1.15 million) jackpot, along with an AUS$48,000 (US$37,600) Powerball prize not too long after. All in all, his winnings totaled about AUS$2.5 million (US$1.6 million).

For a while, the couple was living large. Massetti spent his winnings on high-end European cars, Tag Heuer watches, and Tiffany jewelry. He also gifted Prebble Louis Vuitton handbags and dropped $50,000 on a pair of plane tickets to travel first class to various destinations including Dubai, Singapore, and Hong Kong.

"You get bugger all for flying class," Massetti admitted. "We had caviar and champagne, but to be honest it was a complete rip-off — you are better off flying business class for $5,000 a ticket."

Things started going downhill when a $50,000 hospital donation from Massetti was made public. He had tried to keep his lottery winnings out of the public eye, but from then on, people started coming out of the woodwork to pressure him for handouts.

"Every man and his dog wanted money from me," Massetti said. "I didn't give my friends a drink or give them one single cent — that was my choice. They were obviously annoyed and disappointed, but I said, 'If you don't respect that, don't be my friend and lose my number.'"

While he started to lose many "friendships," the relationship he had with Prebble was also heading south. She accused him of domestic violence, after which he was sent to remand prison where inmates targeted him for his wealth and physically assaulted him.

"I was treated like a dog and had a hell of a time in protective custody," he recollected in an interview. "It's made me a nervous wreck. I don't believe police understand that with my mental health issues I can come across as arrogant and rude. I can't help it. It's part of my bipolar condition."

Prebble admitted that she never actually wanted her former partner to go to prison, nor was she expecting it all to play out that way. To prevent him from meeting that fate, she did not show up on the day of Massetti's court hearing. Police were unable to locate her for the hearing, and she led them on to believe that she had already flown back to New Zealand. She also had the domestic violence charges revoked.

"He has bipolar disorder; prison wasn't going to be giving him the help he needed," Prebble told the New Zealand Herald.

After Massetti left the court building, Prebble was outside waiting to greet him. Their relationship seemed to be on the mend when the pair hugged and walked away hand-in-hand, but sadly there was no happy ending in sight.

"I've been to hell and back," Massetti said of the court hearing and charges. "It's turned my life upside down. I have never felt so humiliated. The charges were thrown out of court, but it has destroyed my life. As a result, I have been diagnosed with post-traumatic stress disorder and severe depression."

The couple is officially separated, but not without each of them accusing the other of being responsible for turning the relationship sour. Prebble, who maintains that Massetti demonstrated "abusive" behavior, moved back to New Zealand following the breakup. She is currently working in a job that involves nursing the elderly and is spending time mending her life.

"For five years he had it in his head I was cheating on him," she said of her ex. "The saddest thing is I left my marriage for someone I thought was genuine and loved me. I am devastated."

On the other hand, Massetti argued that he was the victim in the relationship after he "genuinely tried to love" Prebble.

"I don't hate her, and I'm sorry it's come to this," he said. "I forgive her, but I can't forget what happened."

While it's unclear how much of his wealth remains, Massetti claims that he has enough money to live off through investments. Prebble, however, is convinced "a million percent" that he spent it all.

Massetti has also had a few more run-ins with the law that landed him fines for public urination and drunk driving. Police statements describe him as intoxicated and belligerent while refusing to cooperate and reportedly coughed toward officers after claiming he had coronavirus.

Even after the chaotic events that supposedly squandered Massetti's winnings and led to the deterioration of their relationship, Prebble admitted that she still has feelings for him.

"My affection for Carlo runs deep," she explained. "We shared a lot, and I think we still have a connection. I still love this man — I can see beyond his illness; I see the person inside of him. The man won Lotto, but he's not a lucky man at all."

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