The Drunk Gambler Who Taught Me Everything About Options Trading

Why Your "Winner" Trades Might Be Teaching You All the Wrong Lessons

There's a moment that every options trader experiences, usually after their third or fourth consecutive winner, where they start believing they've cracked the code.

The market whispers sweet nothings. Position sizing stops mattering. Risk management becomes something other traders worry about. And in that moment of supreme confidence, you place the trade that humbles you back to reality.

I watched this exact scenario play out on a $1 craps table in downtown Las Vegas thirty years ago, and it fundamentally changed how I think about probability, process, and why most retail traders lose money despite occasionally being "right."

The Setup: When Being Smart Feels Stupid

Back when I lived in Flagstaff, Arizona, I'd occasionally make the drive to Vegas with a simple mission: place the only bet in the casino where the house doesn't have an edge.

For the uninitiated, craps offers something called "free odds", a bet you place behind your initial pass line wager that carries zero house advantage. The payout is exactly proportional to the true probability. The casino makes nothing on it.

Why would they offer this?

Because most players don't understand it exists. Or they do, but it's too boring compared to the excitement of proposition bets flashing 30:1 payouts across the felt.

Sound familiar? It should. The options market works the same way.

That particular evening, I found a table with $1 minimums and 100x odds, the holy grail for anyone who understands expected value. I brought exactly $100, not because I was being cheap, but because defining risk before you enter a position is the only way to survive markets that are designed to transfer money from the undisciplined to the patient.

Enter the Hero (Spoiler: He's Not the Hero)

Within ten minutes, I was standing next to a gentleman who was three drinks past sober and absolutely on fire.

He'd tripled his chip stack in the last hour.

Let that sink in. Three times his chips in sixty minutes, making every low-probability bet the table offered. Hard eights. Yo-elevens. Horn bets that make casinos send their executives' kids to Ivy League schools.

And he was winning.

Meanwhile, I was methodically grinding away with the mathematically optimal strategy, pass line bets backed with maximum odds, and watching my $1000 slowly bleed toward $700, then $500, then a painful $300.

The crowd loved him. Strangers gathered to watch this drunken savant defy probability itself. Someone actually said, "This guy's got a system!"

No one paid attention to the boring guy in the corner making the "correct" bets and losing.

The Uncomfortable Truth About Randomness

Here's what nobody tells you when you start trading: Short-term results are a terrible teacher.

In small sample sizes, whether that's one night at a craps table or your first twenty options trades, randomness dominates. Luck masquerades as skill. Bad process gets rewarded while good process gets punished.

This is where most traders derail.

They take a directional bet on earnings, get lucky with a move, and conclude they're good at predicting earnings. They sell a naked put, it expires worthless, and they think they've discovered free money. They see someone on Twitter posting 300% returns on 0DTE options and assume that person has superior knowledge rather than survivorship bias.

The drunk gambler was teaching everyone around that table the wrong lesson: that excitement and intuition beat mathematics.

But I knew something the crowd didn't: His fate was already sealed.

When Confidence Becomes the Enemy

Then came the moment I've seen repeated thousands of times in trading accounts.

He started increasing his bet size.

Not because his strategy improved. Not because the probabilities shifted in his favor. Simply because he was winning and felt invincible.

Options traders do this constantly. They hit three winners using short-dated strangles, then decide to deploy 40% of their account on the next trade instead of their usual 5%. They confuse a favorable random sequence with skill and adjust their risk accordingly.

The math doesn't care about your feelings.

Within twenty minutes, the gentleman had returned every dollar of his winnings to the casino, plus his entire stack of chips. The crowd dispersed. The spectacle ended. And I was slightly above break-even, having methodically clawed my way back to $1050 through sheer probability.

What This Has to Do With Your Options Trading

The parallels between that craps table and the options market are uncomfortable:

The Drunk Gambler is the trader buying weekly calls on momentum stocks because "everyone knows" it's going higher. High excitement, low probability, seductive payouts. They win just often enough to stay engaged until they don't.

The Free Odds Bet is the trader systematically selling options with proper position sizing, understanding that edge comes from probabilities playing out over hundreds of trades, not the thrill of individual victories.

The Crowd is every market commentator, Discord channel, and Twitter feed celebrating today's 500% return while ignoring the graveyard of accounts that tried the same strategy and failed.

When I structure trades, whether that's Poor Man's Covered Calls, cash-secured puts, or the various credit spreads I use, I'm making the same decision I made at that craps table: I'm choosing boring, repeatable process over exciting, random outcomes.

I'm choosing to sell options to the drunk gamblers.

The 80/20 Framework Nobody Talks About

Here's something that makes most options educators uncomfortable: I typically sell options with approximately an 80% probability of profit.

Not 95%. Not 50%. Specifically around 80%.

Why?

Because I've learned that being "right" almost 100% of the time means you're not collecting enough premium. You're leaving edge on the table. Meanwhile, targeting 50/50 propositions means you're essentially gambling, any edge gets eroded by transaction costs and behavioral mistakes.

But 80%? That's the sweet spot where probability is firmly in your favor, you're collecting meaningful premium, and you have enough losers to stay humble and disciplined.

Those 20% of trades that go against me? They're not failures. They're the cost of doing business when you're running a systematic process. The casino doesn't panic when someone hits a jackpot, they know the math works over thousands of spins.

Your trading account should operate the same way.

Process Over Outcomes: The Hardest Lesson in Markets

That night in Vegas, I learned something that took years to truly internalize:

Judge your decisions by the quality of your process, not the randomness of short-term results.

The drunk gambler made terrible decisions that happened to work, until they didn't. I made optimal decisions that temporarily failed, until probability reasserted itself.

Most retail traders do the opposite: they judge every trade by its outcome, then reverse-engineer a narrative about why they were "right" or "wrong." They abandon good strategies during inevitable drawdowns and embrace bad strategies during lucky runs.

This is why systematic options selling works. It removes discretion. It eliminates the temptation to increase size after winners or abandon the strategy after losers. It accepts that randomness exists but trusts that probability wins over time.

The Question You Should Ask Before Every Trade

Before I enter any position, I ask myself one question:

"If I made this exact decision 100 times with the same probabilities, would I expect to profit?"

Not, "Do I think this stock will go up?"
Not, "Is this earnings report going to beat?"
Not, "What's my win rate on this setup?"

Just: Does the probability justify the risk I'm taking?

If you're buying options, you're the drunk gambler, betting on low-probability outcomes with capped gains and total risk. Occasionally you'll triple your paycheck. More often, you'll give it all back.

If you're selling options systematically, you're the casino, grinding out small, positive expected-value transactions that compound over time. Boring? Absolutely. Profitable? The math says yes.

The Invitation

I write these articles not to sell you a dream of 1,000% returns or secret indicators that "Wall Street doesn't want you to know about."

I write them because after 24+ years of trading options, from paper tickets on Manhattan floors to today's 0DTE chaos, I've learned that the best traders or investors aren't the ones making the most exciting trades.

They're the ones making the most boring trades, consistently, with proper risk management, over years.

If that resonates with you, if you're tired of the gambling mentality that pervades most options education, if you want to understand how to actually structure trades with probability on your side...

Then you're in the right place.

Because the drunk gambler lost everything that night.

But I'm still here, still trading, still compounding.

And that's not luck, it's process.

Probabilities over predictions,

Andy Crowder

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Disclaimer: This is educational content only. Not investment, tax, or legal advice. Options involve risk and aren't suitable for all investors. Examples are illustrative. Real results will vary. Talk to professionals before you risk real money.