How I Offered Up My House Betting on March Madness

Gambling is a lot more fun for me if the stakes are through the roof. Specifically, my roof. Multiple times in my life, and much to the chagrin of my family, I put our house on the line in a sporting event. It’s not as bad as it sounds. Well, you decide.

March Madness is one of the greatest times of the year for a sports gambler. It’s the perfect bridge between the end of football season and the NBA playoffs. The perennial favorites—schools like Gonzaga (which my cousin Jimmy did a pretty good job proving doesn’t actually exist) and Duke (which most of the country wishes didn’t exist)—competing with the Cinderella teams makes for a very entertaining and oftentimes expensive three weeks.

According to the American Gaming Association, 47 million Americans bet nearly $8.5 billion on the NCAA tournament and, miraculously enough, my degenerate friends and I are only responsible for one-third of that figure. Every March the NCAA tournament is said to cost businesses $13 billion in productivity. I guess this assumes that people aren’t checking Facebook and Instagram all day anyway. But you get the point: The NCAA tournament is a huge deal.

And it all starts with filling out a bracket. The physical act of filling out a bracket is fairly painless. I ran the office pool at Jimmy Kimmel Live! for 15 years. I tried to involve everyone from the die-hard hoops fans to the people who didn’t want to be bothered. I recruited anyone I could—mostly because it was funny for Jimmy to report during the monologue that, going into Final Four weekend, the woman in accounting who refused to keep a television in her house was beating 75 ESPN addicts.

The point is, with just a little guidance, even people who didn’t know a basketball from a bocce ball were able to get through the grid. Filling out a bracket is simple. Filling out a perfect bracket is impossible. Not exactly impossible. You actually have a 1 in 9,223,372,036,854,775,808 chance of predicting every tournament game correctly from start to finish. That’s 9.2 quintillion. To put that in perspective, this book has a better chance of outselling the Harry Potter franchise than you have of filling out a perfect bracket. These astronomically stupid odds led me to an astronomically brilliant idea.

I was going to offer up my house to anyone who was able to fill out a perfect bracket. My lawyer and agent advised against it—especially when I told them I was going to pull a blackjack move and pass on buying the insurance. I brought the notion to Jimmy, who thought it was a great idea, and that’s all I really needed to get the wheels in motion. I went home one night after work and realized my wife also lived in that house, so I would need to convince her that I wanted to risk putting our family on the street.

I should explain that I am not good at breaking big news, specifically the timing part of breaking big news. Back in the late ’90s I told my then girlfriend of eight years I was moving from New York to Los Angeles a week and a half before I left. Actually, my cousin Sally told her before I “had a chance to.” The point is, when it comes to this stuff, I am a thoughtless asshole. So when it came to telling my wife about this contest idea, I thought it best to break it to her during the car ride over to dinner … on Valentine’s Day.

What better way to celebrate the love of your life than by explaining that the home we had worked decades to afford a down payment on could potentially be transferred to a stranger who spent 30 seconds scribbling down a few school names?

Well, it worked like a charm. My wife actually began weeping. When she recovered emotionally, she agreed to the contest … sort of. She announced she was never leaving the house, so she would just live with whoever won. I pictured in my mind my children being raised by the scumbag Russian hacker who was able to create an algorithm to beat my gimmick.

I checked in with other family members. When I told my mother, she disgustedly shook her head. When I told my Aunt Chippy, she smacked me.

After the concussion I suffered at her nicotine-stained hands subsided, I decided to sit down and do the math. I figured that if things went awry and there was a perfect bracket still alive going into the final week, I would fly my fat ass out to Vegas and keep betting the results the perfect bracket had. For a few thousand dollars I could hedge my way back to the market value of my abode. That’s how crazy these odds were. If there were multiple perfect brackets still in play, I’d be screwed.

The contest would run on FoxSports.com and SI.com concurrently, and Tostitos would sponsor it. We started with 250,000 entries. I requested a full report from the web engineer after every four games as to how many people remained. By the end of Thursday night there were 15,000 left, and after Friday night there was exactly one perfect bracket remaining. That lone survivor would have to pick the next 35 games correctly. Not happening. In fact, the dude was eliminated after the first game on Saturday.

And here’s the sick part: I was actually bummed. This wasn’t nearly enough of a thrill for me. What kind of masochistic feeling was this? Kind of like asking for your broken finger to be amputated when all it needs is a splint.

Warren Buffett, one of the wisest financial minds out there, promises $1 million a year for life for the perfect bracket. But he can afford it. I own one house. Warren Buffett owns Nebraska. Yet even he knows not to go overboard with this gimmick.

I’ve already toyed with adjustments for future contests. Maybe have a perfect bracket through two weekends? Perfect through the first three rounds? Eventually, I’ll hand my house over on a silver platter. Pick the play-in games right and you get to live in the garage. It’s just a matter of time before I lose this bet and Oleg is having his way with my wife once a week in the master bedroom.

Excerpt from the book You Can’t Lose Them All. Text © 2021 Sal Iacono. Reprinted by permission of Twelve/Hachette Book Group. All rights reserved. This excerpt has been lightly edited for clarity.