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Illustration by Mr Seth Armstrong

EPISODE 20: GENERATION GAME

When I reminisce about boyhood holidays, my memories often include board games and grey flannel. Back then I loved the former and hated the latter. Now as a father, my seven-year-old son has got me to rethink both. Nicholas discovered Monopoly in October when Hurricane Sandy kept New York kids inside for days at a time with nothing to do but break into the stores of Halloween candy and torment their homebound parents with sugar-fuelled cries of, "I'm bored".

Nicholas took to the game, and he would often have the board set up on Friday nights where my cocktail snacks and ice bucket once greeted me. My wife, Honor, had beaten me home from the office a few weeks ago and merely said, "Take over," when I walked in the door. I quickly scanned the portfolio she had left me - the two most luxurious properties (Boardwalk and Park Place) - but only $100 left of the $1,500 seed capital.

"You're kidding me?" I replied. "Property rich, cash poor. This is the story of our lives." We had recently thrown every red cent we had at purchasing a new apartment and had enjoyed some of our most spirited arguments during the renovation. My wife had a failure of imagination when it came to envisioning why I needed a restaurant-quality ventilation system that would allow me to grill a steak with the reckless abandon of a cowboy on a cattle drive. I had failed her as a husband when I was unable to grasp why we needed any window coverings, towel bars or rugs.

Meanwhile, across the table sat our son, grinning. Nicholas had piles of cash and had fashioned himself into the Dracula Slum Lord of Atlantic City. While I had been riding the subway home, he had erected a gleaming row of hotels along the cheapest properties. "Please, Dad, sit down. Relax. Pour yourself a drink. It's your roll," said the spider to the fly.

My wife failed to understand why I needed a restaurant-quality ventilation system to allow me to grill a steak with the reckless abandon of a cowboy on a cattle drive

As I rolled the dice, I debated whether to go easy on the heir or teach him a life lesson about the importance of keeping a rainy day fund. In addition I was no longer the muffin-faced boy I was the last time I glided the top hat over St Charles Place. I was now the man of the house, a patriarch. I had built an investment portfolio - in real life. I had bought and sold real estate on the cut-throat island of Manhattan. And I had survived the crash of 2008 - a crash in which those who were flying too high on borrowed wings were brought low.

The game between Nicholas and I seesawed back and forth as my son's bedtime came and went, and my first Martini blended into the third. I was struck by how different our approaches to finance are and how Monopoly can serve as a window into a player's attitude towards money.

As a child of the 1970s who remembers standing on an unemployment line with my mother, I once played the game with such an extreme risk aversion that I had no chance of winning. Now I like to control two contiguous monopolies, but not on the most expensive properties: an aspirational address such as Pacific Avenue suits me fine.

In contrast to his dad, Nicholas will buy up properties and burn through his $1,500 grubstake without concern. His perfect portfolio would be to control three asset classes - the railroads, the utilities and cheap real estate. He has no fear of bankruptcy, and I worry that he never will. Money comes to him. He's just one of those fortunate people.

Several times during that Friday-night marathon I had erected a potentially game-ending death trap where I had hotels on six properties in a row. The odds would suggest that he would have to land on one of them and be forced into bankruptcy. Yet somehow he always seems to thread the needle and land on Community Chest. In contrast, his hapless father was forever getting bled dry as he landed on some crack house that Nicholas had gussied up into a boutique hotel.

He likes to keep a running commentary on the game and give me his gloss on the playing styles of our nearest and dearest. "Bird likes to own the railroads," he said of his grandmother, whom he calls "Bird". Our nanny, who is Brazilian, likes to own the utilities. "You're a big deal in Brazil if you own the electric company," he told me.

When I would land on the same space as him, he would yell, "Play date" (which is what he calls it when he and his friends get together after school). When he would secure three of the same coloured properties, he would announce, "I have a monop!" (as opposed to a monopoly). And during one moment when I was cooling my heels in prison (and he landed on Go to Jail), we embraced at our good fortune to be serving hard time together.

Our son had fashioned himself into the Dracula Slum Lord of Atlantic City. 'Please, Dad, sit down. Relax. Pour yourself a drink. It's your roll,' said the spider to the fly

Our Monopoly rivalry burned hot all fall. A fortnight before Christmas, we were locked in one of our fights to the finish when we were both meant to be getting ready for a holiday party. "What do you want to wear to the Christmas carols?" I asked him, hoping to distract him.

"Grey flannels, blue shirt; and Dad, can you tie the red Charvet bow tie for me?"

"Sure," I said, pleased that my little Donald-Trump-in-training and me still had our Charvet bond in tact. "But you really like grey flannels?"

"They're my favourite. I wish I could wear them to school," he replied and I thought about all the times when I was his age that I tried to get out of wearing that fabric. The trousers were itchy, hot and they always seemed to be required for the most painfully boring events.

"Nicholas, why do you like grey flannels so much?"

"They're cosy [one of his favourite words], and they look fancy." He had a point. As a teenager and young adult, I ran the other way from grey flannels. Trying to cheat my way through the holidays with moleskin or corduroys. Not long after seeing him in a pair of flannel trousers, I happened to buy a grey flannel suit, and I loved the way it made even a familiar shirt and tie combination look more vivid and more elegant. It is now a staple of my winter wardrobe.

"Dad, $2,000 please," said Nicholas, as he stirred me from my sartorial reverie. As I scanned the board, I realised I had landed on one of his hotels. The rent would bankrupt me, and I would end up losing again.

To a seven year old.

To read Mr Brodie's previous columns, click here. Follow Mr Brodie on Twitter @jbrodieny

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Canali
Shirt
Charvet
Tie
Canali
Trousers

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