When I was growing up in Venice, I used to play Monopoly every Sunday during the winter with my dad and brother. They were really good, so I usually lost and ended up crying. They were my coaches. I carried this routine into adulthood. During winter, I would go skiing with my friends in the Dolomites. The sun sets quite early there, so we played Monopoly in the evenings. I was a strong player.
One day in 2014, when I was 30 and working as a lawyer for Venice city council, a pop-up banner appeared on my computer, asking: “Are you good at Monopoly?” There was a chance to win a trip for two to the 2015 world championships in Macau, China.
I clicked and signed up first to a regional tournament in Spilimbergo, 60 miles north-east of Venice. I went with my friends. One of them got drunk before the competition and spent two hours playing in silence while wearing sunglasses, but still managed to finish first. I finished third. We both qualified to play in the Italian national championship the next year in Milan.
The tournament took place over two days. The first day I lost all my matches, but on the second I started winning. My girlfriend, Lisa, now my wife, wanted to go back to Venice because she had work the next morning, but I said: “I’m sorry, I’m winning.” By 8pm I had won the national championship. My prize included two flights to play in the world championship in China, that same year.
In Macau, we played in a huge hotel called the Venetian, and I was playing in front of a replica of St Mark’s bell tower. That was odd because I can see the real one from my bedroom. The atmosphere was incredible. There were 27 players from all over the world, as well as fans, journalists, and friends and parents of players. It was a real family event. You weren’t allowed to swear.
Monopoly is a simple game. It’s not chess. If I were to play Monopoly with you, I would probably win because I know the tricks, but in the world championship everyone knows them, so fortune and luck are important. I won that tournament and the prize of $20,580, which is the face value of all the money in the bank in the game.
I started getting calls from people all over the world interested in my win. I also began exploring my passion for standup comedy, developing a routine based on my experiences competing in Monopoly.
I’ve been invited to play in games all over the world. In Japan they are very serious about Monopoly. When I arrived there, I felt like Cristiano Ronaldo. I was taken to meals in skyscraper restaurants with private chefs, and played matches against former world champions.
People ask for tips and I tell them to buy three houses on each property when you own a complete set. Also, jail is your enemy at the beginning of the game, but your best friend towards the end. By then, if you go to jail, stay there for as long as possible because you can collect money off your properties but you don’t go around the board paying other players. There are also Monopoly “heat maps”, which show the places that are landed on the most.
Also, read the rules. Knowing them properly will help you win. For example, you can buy and build houses any time between other people’s turns, not only when it’s your turn. While Monopoly can take hours to finish, the game that got me my world title was over in 47 minutes. That is not because I am the Maradona of Monopoly but because I know the rules. It shouldn’t be a five-hour game.
Winning the championship was life-changing. I started working with Comedy Central. When I travel abroad and contact comedy clubs, I’ve discovered that if I say I’m the Monopoly world champion and have worked with Comedy Central, someone will find a spot for me. When James May came out here to film his series Our Man in Italy, I was invited to speak to him on the show.
The world championships are held every four to six years. The 2021 championship was cancelled because of Covid and there is no confirmed date for the next one. When it comes, I hope to win again. Nobody has won the title twice.
• As told to Daniel Dylan Wray
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