I Won Second Prize in a Beauty Contest and Collected More Than $10

Since the day I could count, my brother and I battled dozens of times in family tournaments of Monopoly. Before each match, he would confront me with his antagonizing, big-brother, I-am-the-boss-of-you tone.

“Ready to lose another game of MO-NOP-O-LY, Dave-IT?”

Expecting an inescapable wrestling hold if I refused, I gave in to his demands. After all, my brother was the Monopoly Master. And an asshole. Every game, when it was his turn to roll the dice, he shrieked a blood-curdling battle cry, jumped about the table, and smugly advanced his unauthorized Indian Warrior token around the game board. He often flicked my token out of the way while he plowed right by me on his path to victory. On my path to bankruptcy, I quietly hunkered down and routinely collected the same old, mundane card from the Community Chest pile: You have won Second Prize in a Beauty Contest. Collect $10.

During each painful game, my brother demanded we follow the official Parker Brothers rules – which guaranteed a long, spiraling, agonizing death for the loser. I lost every game, every time – only to be volunteered to play another. Despite my guaranteed suffering, I looked forward to my complimentary beauty prize.

“Look Dave-IT! You won second prize in a beauty contest! Again! Bwa ha ha ha!”

My life exactly.

For decades, I hated my older brother. I was convinced he had a smirk on his face the day I was born. Everyone in the family considered him Top Banana. He readily agreed with the family’s consensus and had no trouble seating himself in a comfortable position atop the family totem pole. After all, he was smarter, stronger, faster, tougher, and cooler than the rest of us. It was clear to everyone I was the little brother, a second-place token.

Surprisingly, several years ago, my brother began to soften. During an unscheduled visit, he asked me to join him in a round of golf. Based on my first-hand experience with his fierce, belligerent and competitive persona, I feared the worst and politely declined. Meanwhile, he unlocked that old Indian Warrior token from a small safe and slipped it into his pocket.

“How about a game of  Monopoly instead, shall we?”

This time, however, the competition was a bit different – he didn’t call me Dave-IT.

A few years later, when our father was ill, I spoke to my brother on the phone dozens of times. In fact, we spoke more in a two-week period than in the previous two decades. Oddly enough, I began to think differently about our relationship. Although he was still the epitome of a big-brother asshole, I began to reminisce about an alternate reality I couldn’t refute: he was instrumental in influencing me during my formative years in several positive ways.

I scribbled each of them down on a sheet of paper. I read them out loud. My brother taught me;

• How to tie my shoes
• How to ride a bike
• How to fisher
• How to play poker
• How to play chess
• How to lift weights
• How to exercise
• How to maintain my car

And most importantly, my brother taught me how to be successful with his mastermind Monopoly skills – talents I’ve readily exploited to become a competent and competitive adult. It took me a while, but over the years, I cultivated a reasonable level of confidence, I developed valuable negotiation techniques, and I’ve learned successful management strategies. Thankfully, I rejected my brother’s persistent How to be an Asshole education.

Slowly, the Monopoly madness took a back seat in my memory. Although I repeatedly collected the second-place beauty prize during every Monopoly match, I also collected valuable life-skills worth far more than a few bucks of play money. I began to appreciate my brother’s sincere efforts to spend quality time with me at a young age. Without his influence, I’m certain I would have grown to be much more Metro than I’ve allegedly become. In fact, finally, I may be worthy of rivaling that top spot atop the family totem pole.

Today, I almost like my older brother. However, I’m not quite ready to forgive and forget those years of Monopoly madness. In fact, it may be time for the final match of them all. It’s my turn to call the shots.

“Ready to lose your first game of MO-NOP-O-LY, old man? Let’s play a few rounds. It’s your turn to collect the second-place beauty prize.”

Meanwhile, I hope to return the favor and provide him with a few life skills I’ve mastered that may prove to be far more valuable than $10 of Monopoly money.

Photo @Dave Pacailler All Rights Reserved



Dave Pacailler

After living under a rock for nearly 25 years, Dave had his eyes opened wide to the world in 2010 after marrying his crazy cat lady wife. Intrigued by controversy, culture, lifestyle, current events and history, Dave has traveled to 41 states and a handful of foreign countries. Defined as ‘metro’ by his three kids, you will often find him cleaning the house instead of working out in the yard. In his spare time, Dave likes to write sappy love songs but will be the first to admit that he can’t carry a tune. Living in Florida, Dave endures quite a comedic life with his wife, teenage stepdaughter, five cats and a dog that no one likes.

Leave a Reply

Your email address will not be published. Required fields are marked *