The 167-mile journey from my home in Destin, Florida, to the front entrance of the casino in Biloxi, Mississippi, usually took three hours to drive. But today, driving my Ferrari at speeds of up to 200 miles per hour, I arrived in record time—one hour and fifty-nine minutes. Normally, I would have summoned the casino’s private jet, but this was no pleasure trip.

The time was four o’clock when I skidded to a stop in front of the main entrance. “Take care of my baby,” I told the valet, shouting above the theme song to Rocky that was still blaring through my stereo. As I walked into the temple of temptation, I knew it was only a couple of minutes before the adrenalin rush of holding two dice over a crowded craps table would make the exhilaration of driving at Indy car speeds pale in comparison.

“Good afternoon, Mr. Lehmann,” the concierge hailed, barely catching a glimpse of me as I rushed right past the VIP lounge. “Shall I prepare the Presidential Penthouse, sir, and make dining arrangements for this evening?”

“No, thank you—not tonight, Lou,” I hollered back. “If all goes well, I’ll be out of here in a heartbeat.” Hidden by my loose-fitting Tommy Bahama shirt was $250,000 crammed in the waistband of my Levi’s blue jeans. My quarter million dollar bankroll was in five rubber-banded wads—each wad made up of crisp $100 bills.

Throwing those bundles of cold hard cash on the table and declaring, “Money plays,” was one hell of a thrill. High-stakes gambling is all about image, ego, and self-confidence. Never let them see you sweat was my motto—no matter how high the stakes. And trust me—gambling with six-and seven-figure bankrolls, especially when you have to win, completely eliminates the game’s entertainment value. Tonight was strictly business. The question was who would win—me or them?

The table crew is made up of a box man, who sits on one side and oversees the action, a stickman, who stands directly across from him and controls the dice, and two dealers, one on each side of the stickman, who pay and retrieve all the bets on their side of the table. As the box man counted the cash, standard protocol required that he notify the pit boss, who oversaw all the craps tables, that big money was in play. He, in turn, notified the shift manager, the overseer of the entire casino, who then gave a heads-up to the surveillance room. Soon thereafter, security guards—fueling speculation that I could break the bank—cordoned off the table to keep onlookers, spectators, and chip thieves at arm’s length.

“New shooter coming out!” the stickman yelled. “Place your pass line and horn bets.”  The pass line bet is the most fundamental wager on the craps table. Because the house only holds a 1.41 % edge, it’s the best bet to make. A 7 or 11 rolled on the come-out (first roll) is an automatic pass line winner, while the 2, 3, and 12 (called craps numbers) are automatic losers. Any other number is the point, which has to be repeated before a seven appears for the pass line bet to win. The horn bet is a one-roll bet simultaneously made on the 2, 3, 11, and 12 since they can’t be established as point numbers. While the pay-off is high if they hit, they’re sucker bets that give the casino an outrageous edge of 11.1% to 16.7%.

As an expert craps player, I knew the importance of proper management of my bankroll, bet-to-bankroll ratios, and the best strategies to play—and I knew how to execute them with precision. In addition, I had memorized the thirty-six combinations that can come up when throwing a pair of standard ¾-inch, six-sided dice, as well as the odds and probabilities of those combinations appearing. I knew the difference between the pass and don’t pass (essentially betting against the shooter making his point number before the seven appears) the allure of betting the field (a one-roll wager that the next number rolled will be one of a combination of numbers, i.e. 2, 3, 4, 9, 10, 11, and 12) and in addition to the horn, the other proposition bets in the center of the table known as the hard ways (an additional wager on either the 4, 6, 8, or 10 that they will appear as a 2+2, 3+3, 4+4, and 5+5 respectively before those numbers show any other way or before a 7 appears) But I also knew that, in addition to the mathematical edge a casino employed, I was willingly walking into an atmosphere loaded with umpteen psychological ways to skin me alive. Their biggest weapon? Exploiting a deluge of deceptive feelings that allure a man into defying the odds . . .

After all, reason has no place in an arena of illusion. Never the less, craps still offered players the best odds of any table game. In fact, all things considered, it was the best game in the house—on any given day a highly disciplined craps maven could take a casino to the cleaners.

Unlike baccarat or blackjack, where I was often limited to $50,000 a hand, at craps, I could wager $250,000 on every single roll. Win or lose, craps was the ultimate game to temporarily satisfy my cravings for extreme risk, while simultaneously releasing a flood of endorphins that also made it the perfect aphrodisiac for my equally insatiable sex drive.

The other players had placed their bets, and all eyes were now on me.

“Money plays,” I declared, as I placed a pile of two hundred neatly stacked Benjamin’s—$20,000—on the pass line.

“No bet!” the box man stated. “The maximum bet allowed, sir, is $10,000.” Just then, the shift manager pushed through the spectators and informed him that I was Kevin Lehmann, one of the biggest Craps players in the country, and given special exceptions. From that moment, it was . . . game on!

By placing the maximum pass line bet of $20,000, I was playing a hunch that the seven or eleven would show up on the very first roll. On the other hand, if I placed the minimum amount on the pass line, then rolled the point number, I could make an additional odds bet up to ten times my pass line bet by placing it behind my pass line wager. If the point number is repeated before the seven showed up, I would be paid even money on my pass line bet, but I would get paid additional money over and above my odds bet depending on what point number was rolled.

Dice in hand, I went through my usual pre-throw ritual: lean over the rail and bounce them in front of me a couple of times. As I did, I yelled, “Come on yo!”

“Yo” is a slang term for the number eleven so as not to audibly confuse it with the number seven. Although seven is also an automatic pass line winner on the come-out roll, superstition forbids saying that number aloud. Why? The come-out roll is the only time a player wants to see a seven. After the point number is established, the seven becomes a highly paid assassin that wipes out all bets. Prepared to throw, I set the dice on six and five, my telepathic way of rolling an eleven . . . I again urged everyone to yell for a yo . . . Gripped between my thumb and four fingertips, I tossed the dice in my usual, classic style—about six inches above the table with a slight arch and a little rotation. As the two cubes bounced off the table wall and came to a rest, the stickman shouted, “Four, the point is four! Mark the point and make your place bets, come bets, and hard ways!” Place bets are additional bets made on the other numbers, in this case, the five, six, eight, nine, and ten, that they will appear before the seven.  A come-bet is like a pass line bet; only you’re starting after the original point number has already been established.

The good news? I didn’t roll a two, three, or twelve and automatically lose my $20,000. The bad news? I didn’t roll a seven or an eleven and automatically win $20,000. The ten notwithstanding, four was the worst possible point number. Like its sidekick, the ten, the odds against rolling another four before I rolled a seven were two to one—only three combinations could be rolled to make a ten; seven, conversely, had six ways to show up . . . hence the 2 to 1 odds against the ten appearing before the seven.

Hoping to have won a quick twenty grand, I had already committed eight percent of my entire bankroll to the pass line alone. “What now?” I pondered.

With a robust twenty thousand dollars already committed to the pass line, I could hold off betting the other numbers and just wait for either the four or the seven to show up first. But, I thought to myself, what if I rolled all those other numbers multiple times only to have a prolonged roll end with the seven? That would suck.

My mental mayhem continued . . . I could stay on just the four but place another $20,000 in odds behind it. At 2 to 1 odds, if the four did hit, the total payoff would be $60,000 —not too shabby!

“Are you nuts?” my alter ego spoke up in defiance. “Why not bet the other numbers and rake in some real dough? At the least, split another two percent of your bankroll between them. If the other numbers hit multiple times, just keep parlaying them to the maximum bet limit. Also, what about your money numbers, the six and eight, the two highest probable numbers after the seven? You know, if you bet the farm on the four, and don’t place any bets on them, you’ll kick yourself in the ass every time they appear before the seven shows up. At least split another six grand between them.”

My voice of reason quickly retorted, You know not to ever risk more than 10 percent of your entire wad on any one roll. Take it easy, big guy.

“Fuck that!” my alter ego rebutted. “Throw caution to the wind and just go for broke—right now. Take maximum odds behind the four and place maximum bets on all the other numbers, including the horn and hard ways. If the seven shows up on the very next roll, just do a swan dive from the Presidential Penthouse. Trust me, you won’t even feel the face plant.”

The truth was I could easily have taken that advice before I even got to the casino. Little did the table crew and spectators know that the pressure I was under far exceeded that of the craps table.

Earlier that morning, I had made a huge faux pas. As usual, I was watching Squawk Box on CNBC. The omnipotent Federal Reserve chairman, Alan Greenspan, was to announce a highly anticipated drop in the federal funds rate. The question was, assuming that the rate was lowered at all, whether he would drop it just a quarter of a point or by half a point. In an interest-rate-sensitive stock market at that time, a half-point change could send the market indexes soaring. And that was the gamble: had an anticipated drop already been priced into the market in the days leading up to the decision?

My research and analysis were highly technical: As Mark Haines and the Squawk Box crew covered Alan Greenspan on his way to the meeting that morning, I paid particular attention to his briefcase—specifically, was it bulging or flat? Based on previous meetings, a bulging briefcase indicated an aggressive drop; a flat one indicated no change or a quarter-point drop at most. That morning, his briefcase was bulging.

I immediately called my stockbroker, Del. “At the opening bell, I want you to buy $250,000 worth of out-of-the-money, immediate expiration OEX options contracts.”

He screamed back: “$250,000 worth? They expire at the close today. Are you insane?”

“Yes—to answer a rhetorical question to which you already know the answer—I am insane. Now, just do it before I change my mind.”

Thirty minutes later, he called me back. “I got the order in; make sure you have the funds in here before tomorrow’s open.”

“Just sell enough of my stock to pay for it.”

“I got bad news.”

“What?”

“Your tech holdings are tanking.”

“How much?”

“That’s the other bad news: you’ve generated a margin call of $250,000.”

“Uh oh!”

“Uh oh? What do you mean, uh oh? Don’t tell me you don’t have the money.”

“I don’t have the money.”

“Fuck . . . me!”

“Fuck you?“”Fuck me—I’m the one whose stock is dropping like a rock!”

“Fuck you, fuckball! He snapped back. “I’m the one whose job is on the line for making hedge-fund sized options trades with no money on hand!”

What I liked about Del (a fellow car enthusiast who claimed his father lived vicariously through me) was the fact that, unlike a couple of my other stock brokers, he had moxie and he didn’t placate me just because I was a big client. “Chill out,” I told him. “Let’s see how the market looks by this afternoon.”

At one o’clock, I received another call.

“Dude, the Fed only dropped it a quarter-point, and the market’s sinking faster than the Titanic.”

“Dammit, Greenspan!” I hollered.

“That’s not all,” he continued.

“What now?”

“I got more bad news . . .”

“Go ahead, lay it on me.”

“Your margin call is up to $300,000—”

“Oh shit!”

“And your $250,000 options purchase that you haven’t paid me for yet is down to $100,000.”

“Mother . . . Fucker!”

“Dude, I need $550,000 in here by tomorrow morning’s open, so I hope you’re sittin’ on a boatload of cash.”

“I have a grand total of $250,000 to my name.”

“How are you going to get me $550,000 by morning?”

“You know how.”

“Oh shit! You are one crazy son of a bitch! Ferrari, Porsche, or plane?”

“Ferrari.”

“So, what you’re telling me is that my job, my career, and my credibility are now on the line?”

“No—your job, your career, and your credibility will now be on the pass line.”

That $300,000 shortfall was what had led my Ferrari and me to arrive at the casino in record time. I knew from past experience that, if I had taken the casino’s jet—while I may have arrived sooner, if I won a ton of money―that jet would have been unavailable when I wanted to get the hell out of Dodge.

So, here I was . . .

After weighing the options, I boldly said “Give me $88,000 inside, $40,000 on the outside, $20,000 odds on my four, $10,000 apiece on the hard ways, and what the hell . . . $10,000 in the field.”

True to form, my balls had gotten the best of me as I threw caution to the wind. My decision boiled down to one thing: time. If I was to make it back to Destin with $550,000 in cash before the market’s opening bell at 8:30 tomorrow morning, I had thirteen hours to make it happen. To the novice gambler, that was a long time. As an expert, however, I knew it could take that long for a trend to show up; and even then, nothing was guaranteed. In a negative expectation game (theoretical return over the long run is less than 100%) like craps, time is a double-edged sword. The reason? The house’s vigorish.

Vigorish is the disparity between being paid true odds (a higher amount) and house odds (a lower amount) on any winning number. Vigorish gives the casino a perpetual edge, so to speak, that will unequivocally devour any size bankroll if a player plays long enough. Variants and trends were my only friends, but to capitalize on either one, I would need the patience to wait for them, the wisdom to recognize them, the balls to bet on them, and the chips to capitalize on them.

All told, I had $218,000—87 percent of my bankroll—at stake on one roll. In other words, I was 77 percent over budget right from the start. I’d covered every single number with the maximum bet allowed: $24,000 each on the six and the eight, $20,000 on the five and the nine, $20,000 on the ten, an additional $20,000 on the four, plus $20,000 in odds behind it. I’d also put $10,000 each on the hard way numbers—four, six, eight, and ten.

Word spread quickly that big money was at stake on the craps table, which, in turn, drew groups of astonished spectators from all corners of the casino. I could hear the whispers of people standing behind the guards. “How much money is that?” one lady asked. “Who is he? Is he a celebrity?” “Man, that guy’s got balls!” I was surprised at the nervous empathy that emanated from complete strangers, several of whom were dragging on cigarettes like it was their own money at stake. With $218,000 riding on one roll, even the box man was perspiring so badly that the sweat on his forehead had started to bead.

“Come on, dice!” I shouted, as I hoisted them into the air. They tumbled down the table, bounced off the wall, and—I had a spinner . . . the first die landed on one, but the second die spun . . . and all I could think was “Please, God, don’t let it be a six.”

Continue to Part 2 »