Betting the Impossible: 

The Rise of the World's Greatest Parlay Bettor:

Miles was never the best at school—at least not in a school full of geniuses. We’d both been accepted into a magnet program housed within a larger high school, where the application process was as demanding as applying to college. Our class consisted of 28 students: 25 boys and 3 girls. It often felt like half the class could have graduated high school before it even started. Miles and I were part of the other half.

We quickly became good friends through our shared love of sports, but even then, Miles didn’t seem to belong. I graduated high school at 105 pounds – Miles entered high school as a 6 ft, blue-eyed, blonde haired star soccer player. He did not fit the stereotype of a typical nerd.

There was something about him though—it just took me a while to fully understand it. It’s one thing to be book smart; it’s another to have true ingenuity. Tests are designed to measure mastery of a subject, but what happens when someone can beat the test itself? Miles had an uncanny ability to get into the mindset of the test maker and reverse engineer exams. He could figure out which answers they wanted you to choose and which ones were deliberate misdirection. Through sheer logic and process of elimination, he could find the right answer. This ability to break down complex systems would later allow him to terrorize oddsmakers in ways they never saw coming.

I firmly believe the best way to understand how someone thinks and processes information is to play board games with them. Our high school friend group was obsessed with board games, and Miles was the best of all of us. It wasn’t that the rest of us weren’t good—he was just better. We often had to start games by teaming up against him just to give someone else a chance to win. And honestly, it’s hard to blame us. He eventually went on to become the number one online ranked Catan player in the world.

He possesses an intangible quality that defies traditional measurement—a kind of heightened intuition I like to think of as “common sense on steroids.” He has an uncanny way of seeing the obvious in situations where others are completely blind to it. While our classmates were celebrated as academic geniuses, Miles was a genius in his own way.

After graduation, our friend group went in different directions for college, but the bonds we built in high school stayed strong. Miles and I grew especially close, as our schools were near each other. I even joined multiple intramural teams at his college, winning a few club championships alongside him. Our love for sports never faded, and we came of age just as sports betting was taking off across the country. With endless promotions popping up, we couldn’t wait to turn 21 and take our shot at beating the books. We were certain that our deep knowledge of sports would give us an edge over other bettors.

Halfway through our senior year, the pandemic sent us all back home, abruptly ending the final chapter of our college experience. It was during Covid that our lives finally slowed down, giving our friend group the opportunity to truly focus on betting. With endless free time and the NBA restarting in the bubble, we began our sports betting journey. Like many beginner bettors, we quickly stumbled through the common pitfalls, learning hard lessons along the way. It became clear that opinions and gut feelings didn’t matter—there was no edge in simply “having a feeling." Success required an overarching strategy that could be applied consistently across games. We each tackled the problem from different angles, and while we found some early success, the real world eventually came calling. It was time to start our adult jobs.

Miles moved to Connecticut, and it was in the quiet solitude that he began making real progress on his strategy. He became convinced that sportsbooks had mispriced their odds, he just wasn’t able to pinpoint exactly how. After all, he was placing incredibly long-shot parlays—something every expert warned against as the worst approach for any sports bettor. It was common knowledge oddsmakers made the bulk of their profits from parlays. They were seen as a sucker’s bet, so why was Miles so certain there was an opportunity?

He became obsessed, refining his strategy little by little, inching ever closer to a breakthrough. Reservations started to emerge, but how could he keep getting so close. It couldn’t be luck that so many bet slips had only lost by one or two legs.

And then it happened. A parlay hit: his $10 bet returned over $9,000. The immediate feeling wasn’t joy—it was shock. Did I really just win? Miles wondered. He had grown so numb to losing that the win almost felt surreal. Was this the validation he needed, or was it just blind luck? The doubts crept in almost immediately, and he couldn’t help but question if he could ever replicate the magic.

The prevailing belief was that parlays could never be profitable. Only a handful of sports bettors had ever beaten the books over the long run, and certainly not by relying on lottery-style parlays. If he showed anyone the slip, they would write it off as a fluke—after all, someone had to win occasionally. Maybe, this time, it was just him.

Could the entire world really be wrong?

[CONTINUED BELOW]

He wasn’t sure, but he didn’t need to be. There was no rush to scale up his bets. No one suspected he was onto something—hell, he wasn’t even sure himself. Miles decided to stick with the same $10 sizing but began placing parlays at slightly lower odds. These odds, still upwards of +20000 (1/200), were more than quartered from his earlier bets. He reasoned it would make proving the mispricing easier, as it increased the likelihood of another parlay hitting. Even so, winning two bets at such incredibly long odds remained a statistical improbability, if not an outright impossibility.

And then it happened again. A $10 bet returned $2,400.

The payout may seem small, but to Miles, it meant everything. It confirmed his suspicions: the odds were mispriced in a market widely believed to be unbeatable. He felt vindicated, but questions lingered. How had no one else discovered this? How had something so “obvious” gone unnoticed by everyone? And most importantly, how had the algorithms that sportsbooks depended on failed to catch the mistake?

But the truth was, it wasn’t obvious. No one in the world—not a single bettor, nor the most advanced computer model—had identified the flaw Miles saw so clearly.

Even with this breakthrough, however, he did not know his true hit rate. How often could he realistically expect to win one of his long-shot parlays? To stay cautious, he decided to keep his bankroll at 100 units, betting under the assumption that he would win once out of every hundred wagers. For context, the odds on his parlays were priced for a win rate of less than 1 in 1,000. If his calculations were correct, he had uncovered a strategy with over a 10x edge—unheard of in any market, let alone in sports betting, where the odds are notoriously stacked against bettors.

But Miles had underestimated himself.

His edge wasn’t 10x—it was much larger. As he refined his strategy and honed his skills, his advantage grew to over 25x. In a matter of months, he had gone from a mere hunch to uncovering what could be the greatest inefficiency in gambling history. His modest $10 starting balance had skyrocketed to more than $1.3 million.

If the story had ended there, Miles would already be remembered as the greatest parlay bettor of all time. But this wasn’t the end. It wasn’t even the end of the beginning.

The sportsbooks were just starting to catch on, and I was just entering the picture. Things were about to get exciting.

Don't miss Part 2 - coming next Sunday!