That hat-trick of wins followed earlier wins in 2012 for the former funeral director who hasn't worked since.
In 2018, Massetti was accused of assaulting his partner Danielle Prebble. When she failed to appear in court the charges were dropped.
Massetti says he tried to keep his triple windfall a secret, but a $50,000 hospital donation was made public and then "everyone" wanted to be his friend.
Prebble says: "For five years he had it in his head I was cheating on him. The saddest thing is I left my marriage for someone I thought was genuine and loved me. I am devastated."
It's a story as old as money. The Notorious B.I.G put it so lyrically street with his hit Mo Money Mo Problems. Anxiety and paranoia rubs off money like a contagion.
Even having the chance to spend up large, Massetti tell us, can only lead to greater disappointments.
He paid $50,000 a ticket for the pair to travel first class to Dubai, Singapore, and Hong Kong.
"You get bugger all for flying first class. We had caviar and champagne but to be honest it was a complete rip-off. You are better off flying business class for $5000 a ticket."
Today, instead of moping over that worthless Lotto ticket from last night's $5 million draw, take a good look around at the things to be grateful for - family, friends, pets, nice belongings.
And then consider this: Winning big last night might have been the worst thing that could have ever happened to you.
