I like to gamble. Gamble money on sports. I don’t drink, smoke, do drugs, or frequent, or even occasion, prostitutes. But I do like to gamble. Gamble money on sports.

I’m not alone, of course. People who like to use big numbers say that sports betting is a multibillion-dollar business in these United States. And most of that money is wagered on professional football.

I’ve been told I have a problem. A psychiatrist once said that I gambled in order to escape the reality of life. I told him that’s why everybody does everything. But he had a point. There’s a certain arc to my gambling sprees. An arc that begins with me making modest bets after much study, then ends months later with me having no money.



I have taken some bad beats in my time, as all bettors have. I was on the wrong side of the granddaddy of them all: Mets and Braves, Game 5 of the 1999 NLCS. The total for the game was 7½ runs. I had the over. In the bottom of the 15th at Shea, New York Metropolitan Robin Ventura came up with the bases loaded, one out, and the game tied at 3-3. You can see the problem: With any normal hit, the Mets would win but only one run would score, making the total seven runs (and I’d lose by the loathed hook). I had to somehow get out of this inning and into the 16th. (Notice how I went first-person here. This happens when money is involved.) There was another way I could win, and that was if Ventura hit a home run, which was highly unlikely since Atlanta’s outfielders were practically standing on the dirt behind second. Any blooper and the Mets would win by one. So what happens? Ventura blasts a 2-1 pitch over the right-field fence, Shea Stadium goes nuts, and the final score is 7-3.

Except it isn’t.

As Ventura rounds first base, the infield is flooded with Mets players and fans. They surround Ventura, congratulating him, cheering him, impeding him. I start to feel sick. Then I hear Costas. He thinks they’ll only count one run if Ventura doesn’t somehow shove the well-wishers aside and finish his trot. This is bad because Bob Costas knows everything. I see him years later and ask why he mentioned this in the midst of the bedlam.

“I knew it was important to some,” Costas says. “My dad was a big gambler.”

There’s an old axiom in sports betting: “You never forget losing a fortune because a guy hit a grand-slam single.” In many ways, this is true.

Anyway, I haven’t made a single bet in the last couple of years. But that’s about to change.

It came to me on New Year’s Eve, when I was sitting around with my friend Adam Eget, who manages The World Famous Comedy Store. We were trying to come up with New Year’s resolutions. Adam, sober now for over a year but nonetheless still somewhat interesting, said, “Hey, do New Year’s resolutions always have to be good for you?” The thought had never occurred to me. It’d be a helluva lot easier to stick with a New Year’s resolution if your resolution was to become a big fat guy, right? And I had just watched Week 17 and picked all the relevant games correctly. Was Adam on to something? Within minutes, my decision was made.

“Time to get back on the horse, Adam.”

“Yeah, horses are fun. Let’s do it.”

“No, you idiot, it’s an expression. I meant it’s time to gamble. Gamble money on sports.”

“Oh.”

See, I need Eget to be with me for this thing to work. You could have all the careful handicapping in the world, and you’re still gonna lose. The juice is just too thick. You need an angle, something that makes no sense but works. That’s where Eget comes in. He has no insights. He doesn’t study trends. He’ll often say things like “Which one is the blue team again?” But he can pick ’em. He’s like that squid that picks the winner of the World Cup. He’s very good at one thing; the rest of the time, he’s just a squid.

Also, I don’t drive, but Adam Eget has his big Challenger ready to rip the tar off Route 15 en route to Vegas. Well, as long as I can keep him sober. As soon as he falls off the wagon, he’s a danger on the highway, and when it comes to picking sports, he’s worse than a drunk squid.

The second man I need on my team is Gabe Veltri. Gabe is a professional poker player. He makes his living at limit hold’em, where he joylessly books his 60 hours a week. The important thing about Gabe: There’s no gamble in him. One time I remember walking by a roulette table at the Mirage with Gabe and asking him to guess the number. He said 26. The wheel spun and the little silver ball bounced and landed on 26. We hadn’t bet, but the table had heard. Everybody was going nuts. I said “Gabe, how much do you wish you’d bet a thousand on 26?” “Not at all,” he said. And I’ve never heard him tell that story. It’s not even a story to him. That’s the kind of wingman I need — Gabe will keep me grounded. He’ll also keep me away from the pits, where the serpents wait to offer me free rooms and free meals and other expensive things.

One other benefit with Gabe: When the market tumbled a few years back, he immediately bought a distressed property online, sight unseen. It’s a 2,000-square-foot apartment, just off Fremont Street in Downtown Vegas, where the hustlers and the whores beg and cajole. The apartment is spare. Two beds, which is fine. Eget likes the floor, pushing himself fully clothed into a corner of the room and chain-smoking, AA-style, till he passes out. There’s a safe in the bathroom, where Gabe keeps chips from a dozen different casinos, as well as stacks of crisp, rubber-banded, hundred-dollar bills. When Gabe leaves a casino, he rarely leaves money behind.

So travel and shelter are taken care of. The playoffs start on Saturday. We’ll load up the trunk of the Challenger with more money than I can afford to lose, load up the CD with Billy Joe Shaver, and take to the road.

And somewhere along the way, I’ll come up with a plan.

For Round 1, Norm Macdonald (@normmacdonald) likes Minnesota +7.5, and the Redskins +3. Give him 5,500 units on each.

Art by: PJ McQuade