Sugar Mama: Chasing the Big Poker Score

Filed in Uncategorized by on March 30, 2013

By ‘Proposition’ Nate Taleb

Over the Christmas break in 2011 my status as a poker player was hard to pin down. For years I’d played professionally, making a comfortable rather than luxurious living, but for a variety of reasons the game had slowly worn me down. I was tired of living off an irregular and unreliable income stream, fed up with casinos and their inhabitants, and beset by a growing sense of unease that those hours spent in card rooms came at a significant opportunity cost.

So in March that year I headed off to Europe for a month to get away from the game, see a bit of the world, and give some thought to whatever the fuck I was going to do on my return. It was on the flight home that I resolved to walk away from poker until I had secured a full time job.

Six months of unemployment followed.

When I did find work, a three month public service contract, an initial rush of enormous satisfaction subsided almost immediately. The culture in that office—characterised by a petty and baseless distrust of the people who would call us for help—and had me nostalgic for the company I’d kept at keep at Crown: a diverse melting pot of arrogant businessmen, grumpy old degenerates, thugs with uncertain sources of income, semi-autistic poker nerds, and straight-out vacuous shits 

So when my contract came to an end and I returned to Sydney for the Christmas break I was at something of a crossroads. I wasn’t enthusiastic about returning to poker, but I was open to the prospect. The primary obstacle was a limited bankroll. The games are always great at Star City though, especially over the New Year period, and so I decided I’d roll the dice and jump back in.

It did not start well.

The night before flying out I snuck down to Crown for my comeback at the $2/$5 tables and lost a little over $2,000 in short order.

Then in Sydney it took only three sessions to drop a further $3,300.

While these were significant losses, they weren’t too far out of the ordinary. My approach to the game is aggressive—occasionally reckless—and I am accustomed to big swings. The absolute size of the losses weren’t the issue so much as the relative size: I’d never lost half my net worth before.

Any poker player will tell you that it’s next to impossible to play at your best on scared money. The “ol’Gil needs this” mentality inevitably sets in, and it’s insidious. As it takes hold, every cooler and bad beat begins to confirm what you were already coming to understand: you’ve been cursed from above and will never win again. With shot nerves, opportunities to bluff or make thin value bets start to pass you by. Paradoxically, though, the same doesn’t apply to your longshot drawing hands. They become more enticing than usual because, hey, you’re due.

It’s a nasty mindset and, unfortunately, awareness is not sufficient to overcome it.

Compounding matters in my case, I received a text at the lowest ebb of this run from the guy filling the spare room back in Melbourne. He’d let me know at three days’ notice that he’d be moving out, and just like that my rent doubled to $530 a week.

The smart thing at this point would have been to accept my losses, enjoy the rest of my time in Sydney, and work out how the fuck I was going to get someone to fill the spare room in my overpriced house for the last two months of the lease.

What I did instead, though, was commit in my own mind to an epic binge at the tables to get unstuck.

Looking back, I still like to think this decision speaks to my tough and resilient character. That it was, if not quite heroic, courageous at the very least.

The alternative that has been put to me by concerned friends, judgmental family members and trained professionals, is that it was the compulsive behaviour of a problem gambler.

The jury’s still out.

Whatever that choice said about me, things did shift in my favour at that point. I had my first morale booster on December 31: a short session in which I played well, ran good, and picked up a sorely needed $1,400. On my way to the exit I found a loose $35 in chips in my pocket that I threw down on lucky 6. The ball hit the wheel directly opposite the six, snaked in and out of various other numbers, before coming to a gentle rest on mine. $1,225 to add to the tally, and I’m starting to wonder if I’m in ‘it was written’ territory.

So that night I enjoyed a relatively laid back NYE in Erskineville, and woke up to greet 2012 with a hangover that wasn’t entirely debilitating. A comparative advantage! Just the rational and well-founded reason I needed to head to Star City and take advantage of the New Year’s Day action.

That is when things got interesting.

The action was indeed great, and I overcame a bad early run to build a deep stack. This is all you ever really want at Star City. The way the games play there are almost always $3K+ stacks on the table, and those are liable to be pushed around with reckless abandon. I've long considered myself better than most with a deep stack, and so with chips in front of me and nowhere to be, I knuckle down and set my sights on making a big score.

It’s at this point that 'Sweetie', an older and lavishly dressed Greek woman, sat down on my immediate right. This is very good news, but not just because she’s a fish with deep pockets.

Sam, a friend of mine from Crown, had given me the tip about Sweetie earlier when I was back in Melbourne. He had recently been in Sydney and was lucky enough to get a run in her private game. An invitation to one of Sweetie’s games was one of the most sought-after in the poker underground. “It’s a much bigger game than the one you’ve been playing” he’d told me, “the game is wild – $2K to buy in, woeful players – half the time they’re betting without even looking at their cards.”

Sam picked up $14K in his run, and I wanted my shot!

Armed with this knowledge, and the good fortune of having Sweetie sit down next to me, I launch into my best impersonation of a charming, fishy gambler. I start by letting her look at my cards during hands; I throw chips around liberally and make questionable plays. I call a re-raise with Ten-Two suited at one point and together we cheer on my flush draw. Then I re-raise with junk hands twice consecutively, making a show of tabling my cards both times.

Shortly after, I made an absurdly large river bet as a bluff, something like three times the size of the pot, and show only Sweetie after my opponent folds. The rule in such situations is that other players can then request to also see your cards. So when my opponent demands “show one show all”, I feign indignation, show the bluff, and go for a smoke.

Sweetie follows me outside.

In the smoking area, before saying a word, she hands me a business card for Club Amore at some address on the North Shore. As it turns out there’s a game there the following night. “You will come!” she almost demands. “Very good game for player like you.”

I’m in.

All that stands between me and a bunch of rich fish is my perilous financial situation.

So I return to the table with an even stronger determination to grind out a big win. Over 22 hours, in a session that is all a bit of a blur, I managed to amass an $8K chipstack—my personal best for a game that size. $6K profit for the session, and I’m back in the black.

It’s midday on January 2 by the time I get home and crash. It’s important I rest up though, because Sweetie’s game kicks off at 8pm.

Next week in part 2, Nate goes through the highs and lows of the biggest underground poker game he’s ever played. 


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  1. Anonymous says:

    Is Sweetie a MILF?