The Great Monopoly Money Casino Caper

I mentioned this story recently, and a few folks claimed they’ve never heard it. This amazes me, because it’s one of my favorite stories.

In the late 1990s, my wife Lj worked for Saxon Publishing, a Norman, OK company that made math textbooks. Its staff, unsurprisingly, had a lot of people with mathematics degrees who wrote, designed, and edited the math texts, and even fielded questions from school boards about the hows and whys of their style of teaching math.

One year for their Christmas party, which I attended with Lj, they had a professional for-fun-only casino come in. Everyone was given 10,000 of “Monopoly money.” There was a roulette wheel, craps, poker, blackjack, and a horseracing track. We were to play for 2 hours, and then the three people who had the most Monopoly money would get prizes. Lj didn’t want to play so she gave me her 10k, doubling my stake.

The mathematicians all rushed to whatever game of skill or chance they had pet theories on. Blackjack and poker were the most common, but several wanted to try betting schemes (double every bet until you win, then start back at the minimum and double every bet until you win, or variants thereof) at craps or roulette. I wandered by every table before setting down to bet, curious to see how they ran things. The math folks all seemed to be slowly moving ahead at their preferred games, but no one was playing at the horsetrack.

So I went and took a look.

The horsetrack had six My Little Ponies, each with its own lane that has 12 spaces from beginning to the finish line. A deck of cards was used to deal each horse its odds, before the race. An ace was 1:1, a 6 was 6:1, a king was 13:1 and so on. So if you bet $1,000 on a 6:1 pony and it won, you got your original grand back plus an additional 6k. Once all bets were taken, each horse had 1d6 rolled to see how many spaces it moved. Then they’d roll again, and again, until one of more horses crossed the finish line. In case of ties, every horse that won paid out its full winning.

I was flabbergasted.

The thing is, that game has NO connection between the horse’s odds, and its chance of winning. Every horse was just as likely to win, but some paid 13:1, and other 1:1.

Also, you could have a race where every horse paid out 6:1 or better. In other words, you occasionally had races where, if you bet the same amount on every horse, the worst that could happen was you’d break even.

To make sure I really understood the system, I waited until every horse had at least 6:1, and bet $100 on each. As I recall an 8:1 horse won, so I got $800, plus my $100 bet, and lost my other $500 in bets. So I was up $400 on $600 in bets . The nice lady running the game clapped for me. Several math folks looked at me, playing the ponies, and scoffed before turning back to their games of true skill and probability.

I made sure the nice lady running the game saw what had happened, and wasn’t forgetting a rule. She checked with her manager, who’d been running that same game for a decade, and he agreed.

Then, I started betting in earnest.

Anytime the odds were 6:1 or better for every horse, I divided all my money into 6 bets and bet equally on every horse. Since two horses both won at least half the time, and occasionally 3 horses won, even when a high-odds horse wasn’t the winner I’d often double or triple my money. If every horse was at least 4:1 and some were above 10:1, I’d bet a smaller percentage of my money, mostly to encourage the nice lady to have the race, rather than give her time to call out to encourage other people to place their bets before she began. If the odds were bad, I’d throw $100 on each horse to get the race over with quickly.

My money piled up quickly. A $1500 bet on a 10:1 horse brought in $15,000, and even if I lost $7500 in bets on the other 5 horses, I still nearly doubled my money. Then it was a $3000 bet on every horse. Then a $6000 bet on every horse. When I got lucky, I could have three 9:1 or better horses all win. When I wasn’t lucky, I broke even, or had only risked a pittance.

Within half an hour, I had more than $100,000 in Monopoly money. The casino manager had to raid money from other tables to pay me. One of the people with a PHD in mathematics, curious why so much cash was needed, came over. He bragged to Lj that he had doubled his money playing poker. She told him I had *just* crested $250,000. He was stunned.

To his credit, he watched what I was doing for one round of betting, then immediately began to do the same . Of course, I had a quarter of a million Monopoly dollars, and he had less than a tenth of that. He took more risks to try to catch up, and his ability to calculate odds in his head began to let him double his money faster than I could. We had a brief delay when the casino ran out of fake money, and the manager had to write and sign a stack of $100,000 IOUs.

At the end of the two hours, I had $1.5 million Monopies. The mathematician had $250,000. A third person who worked it out late had managed to get $50,000. The next highest total was $15,000.

When Lj and I reported a total, the wife of one of the poker players complained that since we had combined our funds to begin with, we should be forced to each take half and report it that way. I pointed out to her that even if we did that, we’d both have $750,000, and we’d win the first two prizes, instead of just first place. She agreed that wasn’t necessary.

It turns out $1.5 mil Monopie was worth a $50 Godiva chocolates certificate, which we used to buy little mints we froze and put on the pillows of house quests for years to come.

I also offered some thoughts to the casino how to fix the ponies game, which they’d run without issue for a decade. They assured me it wouldn’t be necessary.

About Owen K.C. Stephens

Owen K.C. Stephens Owen Kirker Clifford Stephens is a full-time ttRPG Writer, designer, developer, publisher, and consultant. He's the publisher for Rogue Genius Games, and has served as the Starfinder Design Lead for Paizo Publishing, the Freeport and Pathfinder RPG developer for Green Ronin, a developer for Rite Publishing, and the Editor-in-Chief for Evil Genius Games. Owen has written game material for numerous other companies, including Wizards of the Coast, Kobold Press, White Wolf, Steve Jackson Games and Upper Deck. He also consults, freelances, and in the off season, sleeps. He has a Pateon which supports his online work. You can find it at

Posted on November 30, 2015, in Business of Games, Game Design, Retrospective and tagged . Bookmark the permalink. 2 Comments.

  1. Sounds like a missed career opportunity. I remember once going to a casino with a group of friends. To intimidated to misuse my own money I jovially suggested that one of my friends put all of his money on 0 on the roulette. He obviously refuted this wager…..only for it to land on 0?!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: