The World’s Best
Blackjack Player
The greatest gambling minds on Earth compete
at the annual Blackjack Ball • by Max Rubin

My house, fondly known as "Casa de Mortgage," was built for parties. We’ve had some doozies. So far, though, our best was this year’s "Blackjack Ball" (an event I’ve held annually for the past five years).

It’s mere days after the turn of the Millennium, and 75 of the best blackjack players who’ve ever tricked a pit boss swarm the house, loaded with high hopes and bottles of comped champagne (that’s the price of admission).

Each one is primed, believing that tonight he or she can win the Millennium Blackjack Cup and the title of "World’s Best Blackjack Player."

The joint’s buzzing as blackjack luminaries fill the betting parlor, checking out the parimutuel board to see what kind of opening odds they’re getting. The early line–yes, they’ll bet on and against each other all night–brings a groan from the Hobbit as he sees that he’s going off as the early favorite.

A Hollywood producer/director now, the Hobbit plays only on the big weekends of late, but he was Mensa at 15, hit Vegas at 21, and–thanks to blackjack–got out rich at 30 and set himself up in the film industry. He won the Blackjack Cup three years ago. He’s to be feared. And bet on.

Tommy H., the brains behind the most successful blackjack team in history, makes some courtesy bets on the eight first-stringers he brought along and everyone nods approvingly. The catcalls fly when he’s caught sneaking a few wagers on some of the MIT team’s long shots and he’s hoorayed out of the room.

The line swings wildly and the noise builds as gambling writer and bon vivant Michael Konik makes a huge win/place/show bet. On himself. There’s no shortage of confidence here tonight.

The smart money starts pounding some of the "easy" prop bets, such as "MIT beats ACES Team" at 6/5 (MIT gets all the action) and "Winner is over 40" at 2-1; the money goes with the experience and the latter is bet down to even money in minutes. "Woman will win" at 25-1 doesn’t get a single wager. No surprises there. This is a pretty exclusive boy’s club. The game that will determine the winner is packed with guy stuff and the line would have to be at least 50-1 to get a sniff of action from any self-respecting professional in the know.

The room suddenly falls silent as two people walk in wearing paper bags over their heads–in case casino surveillance crews are lurking outside. The well-dressed guy can be just about anyone, but the woman! She has a natural Victoria’s Secret body, swathed in Versace, and she walks like a gazelle. The guys are sucking in their guts and slicking their hair with their hands as she slowly slips off her mask. Uh oh. Beautiful auburn tresses tumble past her shoulders and she coyly flashes a Doublemint smile that makes my teeth ache.

The tote board doesn’t seem to matter much anymore. Now we all stare enviously and wonder who the lucky guy might be. His mask comes off and it’s the handsome Mr. Lucky. This guy never seems to lose at anything, not since he started gambling 20 years ago. He lives on the ocean in Maui and the rest of his life reads like a James Bond novel, except he gets more girls. He introduces the 20- year-old Olga–he found her while playing blackjack in Russia–as his fiancée and they stroll off to the buffet.

Then another woman I don’t recognize comes to the front door. Now we normally don’t take kindly to strangers at the Blackjack Ball, but she’s a big handsome woman and she’s carrying a bottle of vintage Dom–the kind us oil-patch boys from Texas never even heard of–so I question her further.

She tells me her name’s Cassie, that she graduated from Yale with a degree in economics a couple of years ago, but didn’t feel like going to work right away and decided she’d make her living playing blackjack. I tell her I bet her parents are real happy about blowing a hundred thousand for an Ivy League education so she could play cards, but that stories alone just don’t cut getting an invite to the Ball.

No problem. She leans over and whispers the Greek Team’s secret invitation code. I tell her that she’s welcome and introduce her around to everyone as one of the Greeks. I also explain that she’ll have to be part of the "field bet," which covers all the late entries and long shots. She tosses off some glib comment about how it’s good enough for her just to be here. Some Princeton liberal-artsy guy cracks something wise about Greeks bearing gifts.

For the next couple of hours, some of the best gambling brains on Earth swap yarns while they all get fed, courtesy of Mrs. Rubin, and plastered, courtesy of Caesars and Mirage and MGM. (If you think these guys are good at cards, you ought to see what they can do with a comp.) After dessert, the call goes out and the entire herd of raucous revelers stumbles downstairs to play the game.

The bets fly as I hand out pencils and cards filled with multiple-choice questions. The questions are as simple as knowing the only sport that must be played right-handed (polo) and as complex as calculating the effects–to the hundredth of a percent–of removing a lone five from a single-deck game. The average IQ in the room–with a liberal reduction for me–has to be over 150 and only the top 15 will survive to play the next round.

The room falls quiet as the players scribble their answers. The decibels skyrocket again as the tests are graded and 60 of gambling’s greats fall early. One woman guest who gets only three correct is dubbed "World’s Most Pitiful Blackjack Player," but she takes it like a champ as I give her a big hug and a two-inch plaque. Surprisingly, three other women make it to the second round; that’s never happened before. Early favorites Johnny C., Mr. Lucky, and the Hobbit are all still in it and look like solid wagers. I’ve bet a little something on each of them, so I feel pretty smug.

The field bettors aren’t doing too bad either, with four dogs still in the hunt.

The next round of 15 questions gets much harder, with such stumpers as, "Are you the favorite if your cards total seven and the dealer shows a five?" (you’re not) and "What is Blackjack Forum’s URL?" (it’s RGE21.com). Every question brings a groan and none of the final 15 thinks they’re doing too well.

Finally, it’s the moment of truth. Only the top four will get to sit up on the stage, under the glare of hot lights and jealous colleagues, at the blackjack table. No one gets 15 or 14 right. No one ever has. This year, for the first time, someone nails 13 on the money. It’s Cassie, the Greek. Whoa! She’s the first woman ever to make it to the final table. Also, since she’s in the field, more than half the bettors in the room have something on her. The crowd explodes. 12? No one. 11? Johnny C. dances to the stage, high-fiving all of his backers. How about a 10? Oh no! It’s another field player, the notorious Moray Eel, whom no one expected to be here tonight.

From the sound of the cheers, I might be the only one who forgot to bet the field. All I’m left with is a puny bet on Johnny C. and I have no chance of recouping my losses, unless one of my other "horses" can nab the final seat.

Nine? Four people stand up waving their cards.

Not so fast. There’s only one seat left.

We play a tiebreaker. I spread a deck of cards on the table. Now all these four guys have to do–each with at least a full bottle of champagne in his belly–is memorize the whole deck in 30 seconds. After wobbling and staring for half a minute, they turn their backs on the table.

Mr. Lucky and Pete the Griper go out on the ninth card. Jake Smallwood falters on the 16th. Diamond Mike, one of the more seasoned imbibers in attendance, slurs something that sounds close enough to "Jack" for me, so I declare him the winner of the last coveted seat. It’s a good result: I’m the

only one who bet on him to win.

The table is set and it’s a fearsome and formidable foursome. The players, going counter clockwise from third base are:

Cassie: Yeah, she’s Ivy League, with the Greeks, and makes a great living at the game, but that’s about it. The fact that she’s a woman makes her the big underdog. (You’ll understand why when you see what it takes to win.) Her, I feel a little sorry for.

Johnny C.: A 40-something MIT graduate in computer science, he’s the black sheep of a highly educated family for walking away from Microsoft in the early ’80s. It’s rumored that he’d be sitting on $100 million had he stuck around, but it wouldn’t have mattered anyway. Although he’s got millions, he lives a Spartan life and he’s famous for turning down gourmet comps in favor of the buffet, just so he won’t have to leave a tip. Him, I don’t understand. Continued on...