It’s well-established that I like to gamble from time to time. If there’s a craps table in the room, I’m rolling the dice. If there’s a poker hand being dealt, I’m taking a seat at the table. If there are horses about, I’m going to make them run in a circle for my amusement.

But up until now, I’ve largely sucked at gambling. Why? Because it’s gambling. At best you’re taking educated guesses. As a sports bettor and devout sports addict, my guesses are more educated than most. But even if you know everything there is to know about the teams you’re wagering on, it’s still basically a coin toss.

Until now. Now, I think I finally found a way to win.

You see, for the first time in years I’m on a gambling hot streak. The last two weeks have seen me rake in $1,000+ in winnings, betting almost exclusively college and pro football. To any IRS agents reading this:

I’m just kidding. I don’t gamble. Never have. Please process my unemployment claim. Secondly, go get a job that contributes something to society you vacuous leech.

So how have I created this sudden, unexpected windfall? Was it through sheer dumb luck?

Yes, almost definitely.

No! It was through a total shift in my approach to the game.

Traditionally, I don’t really bet much when football ends. My wallet and mental health both need a break and betting the winter/summer sports is too hard. So when the fall and football season rolls around, I’m way too overeager. I bet too heavy too fast without waiting a few weeks to get the lay of the land on the new season.

What follows is a vicious cycle where I’m down big so I place ridiculously long-odded (Not a word. Not even a hyphenated word) parlays in an attempt to get back to even. As I dig deeper into the hole, the parlays get more improbable until eventually I’m losing virtually every bet.

I was deep in this bitter cycle of losing, self-loathing, and excessive McDonald’s ordering just 3 weeks ago.

But then I got laid off. And all of a sudden, I couldn’t afford to just throw hundreds of dollars down the tube anymore. Technically I couldn’t afford it when I had a job either. It was just easier to justify.

So I realized that I had two basic options:

1. Eliminate gambling all together. Maybe use the time I spent watching late-night Mountain West football to apply to new jobs or learn a skill that could serve me well in my future endeavors. Hell, I could even pick up a hobby just to get out there, meet new people, and really stimulate my brain in new and interesting ways. Christ, I’m bored just writing it. Obviously this wasn’t a viable option.

2. Gamble smarter. It sounds paradoxical. How do you gamble intelligently? It’s impossible. But, there’s a way to gamble disciplined. I realized if I eliminated the careless wagers that were costing me big money, I would be more poised to take advantage when I hit a big bet. Instead of that money simply getting me out of a deep hole, I would actually find myself in the black. This was step one. But even after cutting out the stupid losses, I still needed to find a way to actually win. And then, it hit me.

The Roulette Strategy

Years ago, my family vacationed on some island I’ve since forgotten the name of with our neighbors and great family friends. The hotel we were staying at had a casino. And though I was only 15 or so at the time, I was able to wager because I’ve had facial hair since I was 11.

It was my first real taste of gambling and boy was I in Heaven. We were playing roulette, which is, of course, the ultimate game of chance. Unsurprisingly, I was getting killed. Well, my dad was. I don’t think I owned a wallet at the time.

Basically, I would start with $50 and place single chips all around the board. However, my numbers never came up and I would find myself out of money within 4 or 5 turns of the wheel. I figured that, like carnival games, the casino was simply designed to favor the house and no one could actually win.

(As it turns out, I was 100% correct in this assumption and should have left right there and then, never to return. Would probably be retired by now).

But that’s not what happened. What happened was our friend’s dad explained his strategy to me. He started with much more money than me and would place 3 decent-sized stacks on the same three successive numbers every spin of the wheel. I don’t recall which three numbers they were but for our purposes we’ll say 28, 29, 30. Roulette numbers go in numerical order on the table, but not on the wheel. See below:

As a result, his numbers were relatively spread out on the wheel. Now obviously, there’s a real possibility that he could sit at the table for hours and never see one of his numbers come up. That’s gambling. But because he started with such a large stack of chips, he was able to maximize his opportunities. And all he needed was for one of those numbers to come up once and he was in business. You see, hitting a single number is a 35-1 payout in roulette. So if you have $100 down on that number, you win $3,500 if the ball bounces your way.

In the course of sitting at that table his numbers came up 2-3 times and he netted a nice little profit. I was impressed.

Now he had house money to play with. He could throw a little cash on a sports bet and maybe luck into an even bigger payday. Worst case scenario: he breaks even. It’s a great strategy as far as gambling goes and one that stuck with me.

Oh and I’m well aware that one of you stats nerds could calculate how the house still has a massive edge with this strategy. No shit. They’re the house. It’s about putting yourself in a position to pull one over on them.

Anyways, I thought about that strategy for a while and wondered how I could apply it to sports betting. Then it hit me…

I know football VERY well. But even the greatest football minds in the world can’t tell you how a team will perform on a given day. There’s too many players and too many variables.

But as bad as I am at gambling, I’m that good at fantasy football. Year in and year out, I manage to field a highly competitive team. I can count on one hand the number of times I’ve missed the playoffs across 15 years and dozens of leagues.

So what gives? Why can I field a winning fantasy team, but not a winning betting ticket? Because I was gambling on TEAMS. Fantasy football is about evaluating individual PLAYERS. And I am a very, very good talent scout. So the answer was simple: PROP PARLAYS.

For non-gamblers, that means I select a game like Bears-Lions. And I choose three individual player stats to bet on in that game. In this example game, let’s say I bet on:

• Justin Fields to rush for over 60.5 yards

• Amon-Ra St. Brown to have 5+ catches

• De’Andre Swift to score 1+ TD

All of those bets individually would pay out about even. So you bet $10, you win your $10 back + $10 more if it hits.

When you parlay them however (all 3 need to happen for you to win), the odds skyrocket. You’re looking at a +500 payout. Which means if you bet $10, you win your $10 + an additional $50.

So I decided to shift my betting strategy. A $100 parlay on 3 teams to win would payout around $250 let’s say, assuming all the teams were favored. It seems like a decent return, until you realize that it’s very rare to see all the presumptive favorites win in the same week in the NFL.

But if I place $50 on a prop parlay at +500 odds, I can win that same $250 without risking as much and without being reliant on an entire team. Teams can falter week to week. But superstar players are much more consistent, regardless of their team, which makes their performance easier to predict.

So with the lower risk amounts and higher payouts, I was able to employ the roulette strategy. I placed 3 prop parlays from the games on the Sunday NFL slate. All I needed was for one of them to hit and I would have a highly positive net gain. If all 3-lost, I was only down a small amount. And somehow, it worked:

The first parlay failed miserably. But instead of digging myself a 3-figure hole, I found myself down $40. Then when the second parlay hit, I made that money back and then some.

In other words, I figured out gambling. This blog definitely will not come back to haunt me when I lose all of the money I made this week because I taunted the gambling gods and everything I said was mostly nonsense. No way.