Lotto king Carlo Massetti: Inside the rise and fall of the five-time winner - as he reveals his secrets to collecting millions - and his one big regret Five time Lotto winner's wild life from luxury to a prison cell Carlo Massetti reveals how he won $2.5m from same newsagent Mad romance led woman to claim luxury world tour was a 'kidnap' By Candace Sutton for Daily Mail Australia Published: 21:48, 20 August 2023 | Updated: 00:29, 21 August 2023 e-mail 36 shares 1 View comments Australia's most notorious Lotto winner has opened up about his wild roller-coaster life - and revealed his tips for winning millions. Carlo Massetti is a five-time Lotto winner who went from incredible wealth to the despair of sharing a jail cell with a paedophile. Mr Massetti told Daily Mail Australia he is now enjoying a quieter existence after the chaos of the past, which involved a volatile relationship with a younger lover who sensationally claimed their first-class world trip was 'a kidnap'. The former funeral home undertaker pocketed millions in an astonishing winning streak - once buying three winning tickets in ten days from the same Sydney beachside newsagent. But most of his winnings are now gone, gobbled up by legal fees and the tax office. 'These days I get on with life the best I can,' he told Daily Mail Australia. And Mr Massetti has no desire to have any contact with his ex-girlfriend Danielle Prebble, who is back in the news after being charged with drug-driving and receiving stolen property. Ms Prebble made national headlines after Mr Massetti was dramatically released from prison into her arms outside Sydney's Waverley Local Court in 2019. 'We no longer have anything to do with each other and, of course, I blame myself but it cost me my marriage and the very nice life I was having.' Five-time Lotto winner Carlo Massetti (pictured) had a winning formula for taking home millions, and reaped $2.55m from tickets bought at the same Bondi Beach newsagent Mr Massetti had a tumultuous relationship with Danielle Prebble (pictured), which he said was now over and he no longer had any contact with the 33-year-old - who is now facing charges Mr Massetti said he has chosen to come forward about his life after years of controversial media reports, saying 'my life these days is more peaceful where I can focus on my health and put the past behind almost like a closed book'. Mr Massetti's Lotto streak began back in 2012, when he won two big Lotto payouts and quit his job as a funeral home undertaker in Bondi, in Sydney's eastern suburbs. The New Zealand-born Australian resident had bought Lotto tickets from a newsagent at Westfield Bondi Junction using the same formula that eventually would make him a five-time winner. Mr Massetti's winning Lotto formula involved spending about $5,000 to $8,000 with a system entry ticket, choosing eight to nine numbers and nine to ten lines of them, just using 'the numbers spit out of the machine'. Carlo mostly didn't go in for massive Powerball draws of $40million to $100million, instead choosing the smaller-jackpot Monday to Wednesday or Saturday draws when fewer people were entering. In 2018, he then shot to stardom, winning $2.5million from two separate Lotto draws within one week in May of that year - and just 12 days later won another $48,000 in a Powerball draw. Carlo Massetti says he has some regrets about his wild affair with Danni Prebble (above the couple together in happier times) but he no longer has any contact with her Ms Prebble and Mr Massetti are seen in Dubai during the round-the-world trip which he later was accused of having 'kidnapped' her on - but the allegations were never taken any further With the massive win, Mr Massetti donated $50,000 to St Vincent's Hospital's heart and lung unit, after his father and two grandparents suffered multiple heart attacks. He is still proud of his charitable actions, and had wanted the donation kept anonymous, but arrived at the hospital for the plaque-opening ceremony to be mobbed by the media. His new-found wealth poisoned relationships with some 'friends', who 'were obviously annoyed and disappointed' he didn't shout them a drink or give them one single cent'. But Massetti already had a slew of mates from both sides of the track in Sydney who didn't care. Before he met Ms Prebble, he had been married to a woman from an exclusive family of billionaires who were 'friends with the Packers and the Murdochs'. He lived in a mansion on the Gold Coast and his Sydney mates included disgraced former detective Roger Rogerson and Brad Cooper, the former playboy executive jailed over a $11million bribery and fraud in the HIH Insurance collapse. Mr Massetti said he met disgraced former detective Roger Rogerson (pictured) in 2010 and found him to be unfailingly polite and friendly. He was distressed when Rogerson was charged with murdering a drug dealer and locked up for life Mr Massetti befriended several people who had brushes with the law, including jailed killer Ron Medich and former dotcom director Brad Cooper 'I met Roger in 2010 and we'd always keep in touch and meet up for a beer and he'd give me good advice,' said Mr Massetti, who said he was sad Rogerson was caught up in the 2014 murder of drug dealer Jamie Gao, for which he is now serving life. He was on cordial terms with Ron Medich - now also in jail serving 39 years for the 2009 contract murder of Michael McGurk - who he used to meet at Catalina in Rose Bay. Mr Massetti said he owned the luxury Boheme apartment complex in Bondi Beach, where a young Adam Cranston 'rented a car space... always a flash car every week, it was not a problem for him to pay $1,000 a month rent for the space'. Cranston, the son of a former Australian Tax Office executive, is now behind bars awaiting sentence for the Plutus Payroll conspiracy, in which he, his sister Lauren and others siphoned $105million from taxpayers in one of Australia's most serious tax frauds. FIVE TIME LOTTO WINNER'S WINNING FORMULA Carlo Massetti's winning Lotto formula is not for everyone, but it gave him five wins and netted him $2.5m plus. Although he wouldn't enter every week or month, when he did he would spend $5000 - $8000 with a systems entry ticket. He chose 8-9 numbers and 9-10 lines of them, just 'with the numbers spit out of the machine'. Carlo mostly didn't go in for the massive Powerball draws of $40m - $100m, instead choosing the smaller jackpot Monday to Wednesday or Saturday draws when fewer people were entering. He won twice in 2012, and then in 2018 scooped $2.55million. Hw on $2.5m from two separate Lotto draws within one week in May 2018, and just 12 days later won another $48,000 in a Powerball draw. The winning tickets from Mr Massetti's second Lotto streak were bought from Bondi Six-Ways Newsagency, in Hall Street, Bondi. Advertisement In 2016, Mr Massetti was about to make 'one of the major mistakes of my life - I ballsed up my marriage, which I regret to this day'. He had met and fallen for Danielle Prebble and their tumultuous relationship would see him accused of setting her on fire and 'kidnapping her' when they took a first-class round-the-world trip from Sydney to Hong Kong and Dubai using some of his Lotto winnings. Mr Massetti was investigated on both allegations and police found no case to answer, but he would be charged and end up in jail. In the same year as Mr Massetti's 2018 winning Lotto streak, police alleged he assaulted Ms Prebble seven times, taking him into custody twice for purported breaches. On the first occasion, he found himself processed at the massive Metropolitan Remand and Reception Centre at Silverwater, then woken up three days later at 4am to be taken off to Bathurst Correctional Centre, on the NSW Central Tablelands. 'It was very, very scary,' he said. 'I was in protective custody because of the high-profile case of the Lotto win,' he said, adding that prison authorities feared he could become an extortion target behind bars. He was granted bail just before Christmas 2018 after six weeks in prison, eventually resuming contact with Ms Prebble, which eventually led to 'another altercation' and his further imprisonment - this time at the feared Parklea Correctional centre in north-western Sydney. This time, Mr Massetti was given a cellmate in their protection wing, a man he found 'quiet and polite' who was 'very pleasant', enjoyed a lot of reading and was frequently visited by his wife. 'You don't talk about [inmates'] crimes when you're in jail,' Mr Massetti said. It was only later that Carlo Massetti would learn his mild-mannered cellmate was in fact one of the state's worst pedophile offenders: Bryan Grange is serving 30 years for sexually abusing an eight-week-old baby and two girls under five. Grange was recently denied an appeal against the severity of his sentence and three judges of the NSW Court of Criminal Appeal found Grange 'engaged in deliberate, predatory and callous conduct of the most serious kind'. Mr Massetti swapped a luxury life in a Gold Cost mansion (above) for a wild romance and ended up instead occupying a prison cell in Sydney's notorious Parklea jail Carlo Massetti later found out his 'quiet and polite' cellmate at Parklea prison, Bryan Grange (pictured), was one of the state's worst pedophile offenders, serving 30 years for sexually abusing a baby and girls under five In November 2019, after three months in prison for breaching an Apprehended Violence Order against Ms Prebble, Mr Massetti was due before Waverley Local Court on further assault charges against her. But when court officers were unable to find Ms Prebble, who had failed to show up as a key witness in court, the police prosecutor was forced to drop all seven domestic violence charges. It then emerged she had been standing outside Waverley Local Court throughout the entire hearing and she triumphantly embraced Mr Massetti after he was released. Passionately embracing Mr Massetti as he walked out as a mostly free man, as TV cameras filmed the moment, they walked down the street holding hands and Mr Massetti said they would start a family together. Danielle Prebble and Carlo Massetti embrace outside Waverley court in 2019 after she sprung him with a no-show, but the romance was doomed to fail Ms Prebble admitted her failure to enter the court complex 'was a tactic for Carlo to be let free. The charges against him were pretty harsh.' 'I know that Carlo was a good man. He gives me love,' she added. Prosecutors and the magistrate were reportedly annoyed to later learn about this, via media coverage, and Mr Massetti emerged with an 18-month community corrections order on one count of contravening a domestic AVO. Danielle Prebble is before the court on charges of drug-driving on cocaine, methamphetamine and cannabis, and other allegations of receiving stolen property and possessing car number plates The charge related to an incident where he took Ms Prebble's phone off her and threw it into a toilet during a night out drinking in 2018. The stormy romance continued. Over the next few years, Massetti spent big on luxury cars, Tag Heuer watches, Tiffany & Co. jewellery and Louis Vuitton handbags for Ms Prebble, as well as $50,000 on first-class tickets for an around-the-world trip. Mr Massetti said he 'quite naturally' bought his partner gifts with his Lotto winnings, including designer bags 'but not five of them, one or two was plenty'. The couple's relationship began to fall apart and after a final verbal argument, at traffic lights in Brisbane, he returned to New Zealand and the Covid pandemic put paid to much further contact. He said a year after their return from the overseas trip, Queensland Police contacted him about a claim that he had 'kidnapped' Ms Prebble on their luxury overseas trip. Nothing came of the allegations. Ms Prebble chased Mr Massetti to New Zealand to rekindle their 'crazy love' in 2021, saying 'I know we have this s****y s****y history, but I love him a million per cent'. But her passion for the millionaire would end in tears, and after a night of bourbon and coke and playing drinking games, Ms Prebble ended up lying on a road in Oamaru, on New Zealand's South Island, and Mr Massetti was again charged with assault. A New Zealand court dropped the charges against Mr Massetti, who said the affair was finally over with Ms Prebble, who eventually returned to Sydney. Mr Massetti recently learned about Ms Prebble's recent court troubles, but said he had no intention of contacting her. 'I have endured emotional turmoil. These days I get on with life the best I can with a constant reminder over what I have been through over five years,' he said. Asked whether he was still a millionaire, he said, 'what's left is anyone's guess. Much went on legal fees, credit cards and the ATO'. Share or comment on this article: Lotto king Carlo Massetti: Inside the rise and fall of the five-time winner - as he reveals his secrets to collecting millions - and his one big regret e-mail 36 shares Add comment Comments 1 Share what you think Newest Oldest Best rated Worst rated View all The comments below have been moderated in advance. View all The views expressed in the contents above are those of our users and do not necessarily reflect the views of MailOnline. Add your comment Enter your comment By posting your comment you agree to our house rules . Submit Comment Clear Close Do you want to automatically post your MailOnline comments to your Facebook Timeline? Your comment will be posted to MailOnline as usual. 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