Unfortunately, not every trip in my blackjack career went like that episode in Mississippi. Every good player eventually had trips that tried their very soul. For me, one of my worst moments came on the heels of a peak experience. It was early December and I had just surpassed $100,000 for the year. This was always the goal I had been shooting for and this was the first time I’d ever broken that magic mark.

Unfortunately, it came right in the middle of a five-day road trip to Wendover, Nevada, and I had a non-refundable plane ticket with two more days remaining before I was scheduled to return home. Many other players would have bitten the bullet and taken the small hit on their ticket and flown back early. But, not me. I’ve always been frugal and I had built my bankroll up from a small amount by watching my pennies.

The only practical solution was to stay the course and stay in Nevada. And if I was to do that, then it only made sense to play. Despite my recent wins over the first three days in town, the games were still good. The pit bosses were surprisingly friendly and relaxed. All the clubs in town offered deeply dealt single-deck blackjack and exploiting those handheld games was always my specialty. I gave only a fleeting thought to quitting in order to end the year with a six-figure win. Logic dictated that I play as long as possible, for as much as possible, whenever a gravy train like this one appeared.

Unfortunately, logic and fluctuation seldom find their way into the same sentence. The next day felt like I had been cast as the main character in a tragic Greek play. No matter how hard I rowed the boat, I kept finding myself further and further adrift from the shore. When I went to bed that night, I had dumped almost twenty grand—nearly 20 percent of the money I had so diligently won over the entire year. It was a stunning turn of events. However, I knew those swings could happen at my chip levels. There was nothing to do but dig in and hope the last day of my trip went better. I actually slept well that night. Rather than being hounded by nightmares, I was fairly optimistic that the worst that could happen to me had already happened. I anticipated that the next day might reverse the tide and bring some, or perhaps even all, of the money back into the proper hands—mine.

However, the twisted plot continued and the cards stayed brutally cold. I finally caught a little run near the end of my trip and won a few thousand back, but I still ended up down thirty grand for the last two days of my trip.

Did I make a mistake? No. These brief descents into the abyss are to be expected. Obviously, in retrospect, I wished I would have quit and gone home happy. It would have been fun to tell my wife and friends that I finally had hit the big time and won $100,000 for the year. But there is never any way to predict when those negative swings will occur. Playing on that trip was the right thing—even if it left scars.

However, the worst disasters are the ones that afflict players who think they are winning players—but are not.

One infamous Greek lady definitely fit into this latter category. Cassandra was a well-known and long-time high roller on the Las Vegas scene. However, there was one very unusual aspect of her gambling style that distinguished her from typical losers—she preferred playing blackjack with skilled card counters.

Somehow she had a special knack for picking out brainy looking types (guys like Mickey Weinberg), and she’d sit down next to them to evaluate their play. If Cassandra concluded he was a decent card counter, she’d camp at his table and jack her bets up and down in rhythm with his. I’m really not sure how she determined whether they were counters. Maybe she had once tried to become a professional blackjack player herself but didn’t have the personal discipline to make it work. Or perhaps she just looked for young guys who spread their bets dramatically, since normal gamblers tend to stick with the same wager hand after hand.

Despite this clever scheme of hers, the scuttlebutt around Las Vegas was that Cassandra was losing—big time. Rumors circulated through town that she had gone through millions from an inheritance.

The surprising thing was that Cassandra actually struck me as a fairly decent player. She seemed to understand a lot about the game and was astute enough to know how card counting worked. I’m not sure why she lost so much, but I suspect that she never really stuck to basic strategy. Superstitions die hard for some people, and I surmise she often relied on hunches rather than logic. Even if you bet correctly, you can still wind up a net loser by mixing enough bad decisions into the equation. She especially misused the surrender option and tended to throw in almost every hand she didn’t like, particularly when she was losing.

Mickey and I both knew her (though not in the biblical sense) from several encounters in Vegas. She certainly was attractive enough to draw our attention, but I was married and Mickey is probably the pickiest guy I’ve ever met when it comes to women. My guess is he would expect Miss America to also be a gourmet cook and have a Ph.D. in physics before he would commit to her.

Cassandra always reminded me of the line from the Eagles song Witchy Woman—"Raven hair and ruby lips, sparks fly from her fingertips." Not only did this describe her striking looks, it also captured her legendary temper.

Pit bosses treated her like royalty and called her "Countess Cassandra." But behind her back they tagged her Princess-Pain-In-The-Ass for her fiery outbursts and constant demands. Once she got so enraged over being dealt yet another stiff that she tore the two cards in half and threw them at the dealer.

The casinos put up with this behavior because she bet big—and lost big. The reason Mickey and I tolerated Cassandra at our table is that she actually reduced the usual scrutiny we received. She wagered up to $5,000 a hand, and her losses always dwarfed our wins.

She had such a reputation for dumping money, that anyone she befriended was generally viewed in a positive manner by the casino. Even if they suspected we were counting, they rarely wanted to rock the boat and risk upsetting her by kicking us out. As a result, Mickey and I played many sessions at the blackjack tables with Cassandra because we avoided drawing the usual heat when we spread our bets.

Her presence helped us, and our expertise should have also helped Cassandra and made her an overall winner, but somewhere along the line it broke down. Maybe she occasionally went on tilt or started steaming when she lost. It’s easy to do—I’ve seen a lot of levelheaded-looking people get totally out of control once inside a casino.

I have not seen Cassandra at the tables in many years and I assume she finally tapped out and lost her entire fortune. Hers is a true cautionary tale for the thousands of eager players who have read books on blackjack or watched the MIT movie and think they can beat the house at their own game. But for every Legend who succeeds, there are countless others who end up getting crushed by the casinos. And Cassandra sits near the top of that list.