This article originally appeared on VICE Italy.
One of the many memories I associate with playing Monopoly is the first time I got drunk. It was 2009 and I'd just turned 16. I was by the seaside in Liguria, northwest Italy, and I managed to get through six beers and half a bottle of gin in the time it took to finish one game. I cannot remember who won.
That experience didn't ruin my taste for Monopoly and its ability to tease out the self-destructive, greedy, unrestrained capitalist inside all of us. So when my editor suggested I should take on the current Monopoly world champion, Italy's own Nicolò Falcone, I jumped at the chance.
Nicolò is a 34-year-old lawyer from Venice, who also happens to work as a stand-up comedian. "Monopoly is a game based on building haphazardly, playing with fake money, and going in and out of prison," Nicolò often says in his routine, building to the punchline. "So it's natural that Italians are good at it."
To challenge Nicolò in a proper game, I need to recruit two more players. So through an extremely complicated and extensive selection process via one Facebook post, I find Elio and Lidia. Nicolò has asked to bring fellow stand-up comedian Stefano Rapone—not to play, but just so he too can be entertained by our inevitable destruction.
After days of training, which involves reading and rereading the official rules of Monopoly and soliciting tips from former world champion Bjørn Halvard Knappskog, it's game-time. On the morning of the contest, we meet in the VICE offices in Milan. Brief introductions aside, the first task is to pick our tokens, which feature some of the newly designed items and not just the iron, flask, and hat of my youth.
Nicolò picks the vintage car, Lidia picks the T.rex, Elio—who plays in a band called the Pinguini Tattici Nucleari (Tactical Nuclear Penguins)—obviously picks a penguin. To make it clear to everyone that I'm not here to mess around, I select the battleship.
As the oldest player, Nicolò will be the banker. We're playing with an extra dice to speed the game up a bit. Here we... here we... here we fucking go.
The first 30 minutes go as expected, with each player trying to bag all the properties they land on. Elio ends up in prison a few times—a theme that will continue for much of the game, preventing him from establishing an effective property portfolio. As for me, thanks to a couple of fortunate throws, I manage to purchase two of the five most expensive landmarks relatively quickly. And then eventually the big one itself, the most expensive property on the Italian Monopoly board: Parco della Vittoria.
On a high, I make a few shrewd deals with Lidia to swap an electrics company and one of my cheaper properties for the second-most expensive landmark: Viale dei Giardini. I now have a monopoly on the two most expansive and lucrative spots the game has to offer.
Now, obviously, I've spent tons, but I don't care. I grin a giant grin and aggressively mock the other players when they land on any of my properties. Sure, they're only paying me relatively small sums at this stage, but my lord I feel invincible.
Nicolò, though, is staying rather calm and quiet and seems to almost be playing a separate game on his own. He mortgages an electrics company and a station, and he only purchases the orange properties—a popular strategy among the game's elite, as they have the best cost to income ratio, and they're the most likely places other players will land on when leaving prison. Meanwhile, Lidia and Elio have yet to obtain a full set of properties of the same color.
In my mind, at least, it's now a straight shootout between the world champion and me. Soon, we're really building our empires, but after splashing top dollar on a handful of houses, I have, unsurprisingly, run out of money. After a few more turns, Nicolò has also spent most of his cash, but he has hotels as well as homes popping up everywhere. From now on, whoever lands on any of his landmarks risks imminent bankruptcy.
I'm starting to think he's working to some sort of coherent, considered strategy—one that involves more than just buying up the most properties, and instead creating fatal traps that hook and devour his opponents.
The first to end up in his web of debt is Lidia, who's forced to mortgage all the houses she had eventually accumulated, but still hold on to her collection of train stations—which, in any case, are "useless," according to Nicolò.
After feeling a brief twang of personal satisfaction for taking money from the world champion when he lands in my territory, I end up owing him an extortionate amount of rent just a few throws later, forcing me to mortgage a few properties of my own. It's at this point that Nicolò makes it clear that he's done messing around and won't be accepting any properties as debt repayment. All he cares about now is ruining us.
The only player who doesn't end up screwed by Nicolò's tactics is Elio, who—in keeping with the traditions of Italian property magnates—continues to spend a significant amount of time in prison.
Just short of two hours in, the first chicken to be plucked is, of course, me. Rich in property, but cash poor, I end up enjoying a series of unwanted stays in the champ's hotels, and no amount of complex re-mortgaging can save me. As per the rules, my money and land all go to Nicolò. With the money he has accumulated, he builds some actual hotels on my land. The end is nigh.
Five minutes later, Lidia goes bankrupt. Within 15 minutes, jailbird Elio realizes that he started with nothing and pretty much still has nothing. Nicolò kindly gets out his calculator to help Elio work out whether he can be saved from bankruptcy, and whether his execution can be postponed. It cannot. Two hours and 15 minutes after the start of our game, the world Monopoly champion, Nicolò Falcone, has won arguably his greatest battle.
Before we all leave, I ask Nicolò to rate each player. He says Lidia played well but made three key mistakes. The first was that she only put two houses on her three properties, when it's better to build in groups of three, one per property. Her next big mistake came toward the end of the game when she decided to pay off her debt to him by mortgaging her properties and not selling her train stations. Generally, he says, stations and societies won't really help you win, so get rid of them when you can. The key is to build houses and hotels as quickly as possible.
Lastly, he criticizes her for not being ruthless enough and allowing the rest of us to negotiate our way out of debts. "You shouldn't pity anyone," he reminds her. "You must take them down as quickly as possible."
Elio also played well, he says. "But he made a huge mistake in the beginning by staying in prison too long when he should have paid his way out."
Nicolò explains that prison is a good place to spend time at the end of the game, when the risk of paying expensive rents is high, but not at the beginning because you need to get around the board in order to buy up some free contracts of your own.
As for me: "You played alright, really, but you were unlucky," Nicolò assures me. So, sure, having some base knowledge of tactics and strategies might help you become world champion. But for the rest of us, our success at Monopoly, as in life, is pretty much based on two things: pure luck and minimizing your time in jail.
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