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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 WinAfter the Big Win: Australian man who won lottery five times has "been to hell and back"Rating:

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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14 comments. Last comment 26 days ago by Suzy-Dittlenose.
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Tony Numbers's avatar - Lottery-022.jpg
Bronx ny
United States
Member #158510
August 25, 2014
680 Posts
Offline

Easy Come. Easy Go

    Unlucky-Kenny's avatar - Cigar B1.gif
    WISCONSIN
    United States
    Member #202055
    November 7, 2019
    2007 Posts
    Offline

    Talk about luck to win so many prizes like that in that time frame - but then everything else that happened.

    Sad story.

    Ol' Kenny is going to win big just a loser

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      Avatar
      homestead
      United States
      Member #158175
      August 14, 2014
      492 Posts
      Offline

      Talk about luck to win so many prizes like that in that time frame - but then everything else that happened.

      Sad story.

      Sad indeed. The moral to the story is:

      1. If you win the lottery, put the money into a trust fund.
      2. Never tell friends and family about your winnings
      3. Invest the winnings into the stock market so that the prize money can grow 10x the initial amount..

      I seriously doubt that anyone would follow that advice.

        Unluckyone's avatar - lib

        United States
        Member #176412
        August 4, 2016
        231 Posts
        Offline

        This guy won a total of 1.6 million USD and was living it up like he had much more. Flying first class to exotic destinations and buying sports cars especially in Australia will eat up your funds awfully quick. I believe his ex that he is indeed broke unfortunately for him many of us reading this story will use it as a what not to do game plan.

          Avatar
          Chasing $ Millions.
          White Shores- California
          United States
          Member #136471
          December 12, 2012
          6622 Posts
          Online

          Carlo was warned by his friends, but his heart overruled that advice. Well look here..

           * Voice of Reason *   

          * The Truth Hurts *

          People who say it cannot be done should not interrupt those who are doing it- George Bernard Shaw.

            Perfecttiming2's avatar - redcross

            United States
            Member #65959
            October 11, 2008
            206 Posts
            Offline

            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."

            This guy ..... one bad decision after another.  I think the money only magnified what was already there.

              sam9009's avatar - bck
              25
              Brooklyn, NY
              United States
              Member #78505
              August 16, 2009
              34426 Posts
              Offline

              I wonder if he chose his own numbers or QP?

              Invictus maneo

                Perfecttiming2's avatar - redcross

                United States
                Member #65959
                October 11, 2008
                206 Posts
                Offline

                Sad indeed. The moral to the story is:

                1. If you win the lottery, put the money into a trust fund.
                2. Never tell friends and family about your winnings
                3. Invest the winnings into the stock market so that the prize money can grow 10x the initial amount..

                I seriously doubt that anyone would follow that advice.

                I'd like to add:

                4. Have a budget and stick to it 
                5. Donate anonymously (I am sure there are ways to do this)

                ***Don't know if its been done but members on Lottery Post could create an official "Lottery Post Members What To Do / Not Do If You Win List". 
                We've seen many stories over the years to compile a nice list***

                  KY Floyd's avatar - 3 hour-tour.jpg
                  NY
                  United States
                  Member #23834
                  October 16, 2005
                  4405 Posts
                  Offline

                  "Donate anonymously (I am sure there are ways to do this) "

                  One way is to write checks to a lawyer or other agent who will then write checks to whatever cause you're donating to. That's simple, but documents things so you can deduct any donations that are charitable. Or you can get more elaborate and create a legal entity specifically to handle the donations. Not sure how the IRS would feel about the documentation, but for modest donations you could just buy postal money orders.

                  Donating anonymously can be a good idea whether you've won the lottery or not. Large donations could let people know you've got a lot of disposable income, but even modest donations can result in constant begging for more.

                    Avatar
                    ma
                    United States
                    Member #188574
                    March 15, 2018
                    87 Posts
                    Offline

                    High end European cars, jewelry, watches, handbags and 50k plane tickets and all he won was 1.6 million. This is worst than Jack Whittaker who won 300m at least before he started frittering it away and had more fun doing it for a while at least. This guy takes the cake for the most mismanaged lottery hit in history based on the amount he won.

                      HoLeeKau's avatar - 40827 jpg?1576607320
                      Idaho
                      United States
                      Member #94279
                      July 17, 2010
                      2367 Posts
                      Offline

                      High end European cars, jewelry, watches, handbags and 50k plane tickets and all he won was 1.6 million. This is worst than Jack Whittaker who won 300m at least before he started frittering it away and had more fun doing it for a while at least. This guy takes the cake for the most mismanaged lottery hit in history based on the amount he won.

                      Exactly.  $1.6 million isn't much money.  Take $100k for a splurge - car, vacation, whatever you most want.  And what's left is just enough to fund a nice retirement plan.

                        HaveABall's avatar - rocket

                        United States
                        Member #72446
                        March 18, 2009
                        1388 Posts
                        Offline

                        All in all, his winnings totaled about AUS$2.5 million (US$1.6 million).  That was enough for anybody to:

                        • Self invest 90% in plain Momentum ETF fund, then withdraw 7% annually for expenses and insurances,
                        • Retire,
                        • Move to a low taxes location,
                        • Buy a big two bedroom condo with indoor parking, gym, and swimming pool, 
                        • Join a games, breakfast, lunch, or supper club, and
                        • Take a 7-day cruise vacation, annually, until you're up to 100 years old.

                        Having several millions of dollars in my financial accounts means receiving several valuable services each day!

                        Disney

                          KY Floyd's avatar - 3 hour-tour.jpg
                          NY
                          United States
                          Member #23834
                          October 16, 2005
                          4405 Posts
                          Offline

                          FWIW, the US$ total is actually almost $2 million.  37.6k + 783k + 1,150k = $1,970,600

                          There's a good chance that's not enough for a guy who's 47 to retire on because if he lives another 40 years and inflation runs 3% per year by the time he's 87 he'll need $3.17 to equal every $1 he needs today. To take just 5% ($98.8k in US$) now and the inflation adjusted equivalent every year he'd need an annual return of almost 7.5% after taxes.

                            Avatar

                            United States
                            Member #163988
                            February 15, 2015
                            101 Posts
                            Offline

                            Sad indeed. The moral to the story is:

                            1. If you win the lottery, put the money into a trust fund.
                            2. Never tell friends and family about your winnings
                            3. Invest the winnings into the stock market so that the prize money can grow 10x the initial amount..

                            I seriously doubt that anyone would follow that advice.

                            1 & 2 are very good ideas.  I would first legally change my name so no one will know me.  Then I'd turn in the ticket with my new legal name.

                            Sun Smiley