The rise and fall of N.Y. poker

The following story was written by "Matthew21v13," a lifetime money contributor to the underground poker scene.

I cry easily. From an early age, I learned to avoid physical confrontation. That night in New York, however, I knew my cowardice was on a collision course with greed.

I sat at a $5/$10 no-limit table that was groaning under $180,000 in chips and bricks of $100 bills. I held much of it, but I had no safe way home.

It was 4 a.m. The decent people of New York had long ago abandoned this lonely side street with its black puddles and cardboard sleeping bags. I was nervous because, instead of leaving, rounders started showing up. This meant a lot of people were receiving wake-up calls that a drove of donkeys were shoving insane amounts of cash in an underground club poker game. While rounders were jockeying for a seat, shadows were likely gathering in the alley outside.

Hours earlier, I sat down with my $2,000 buy-in. This was big for me, but short for the game. I normally play $2/$5. However, I have recently noticed the only games you can find in Manhattan are $1/$2 baby no-limits or deep-stack $5/$10 tables.

I was not happy with that evening's lineup, as I was clearly the table idiot. The other players, who ranged from loose action junkies to rocks, were all aggressive sharks that had earned the respect of the underground community.

As I sat down, Anon ogled my rack of chips like they were Courtney Friel's breasts. He was a former grinder who had taken to playing like a maniac as his company grew profitable. To his right sat Bob, an affable real estate tycoon who developed the annoying habit of smirking whenever he buried puny continuation bets under mountains of black chips.

Charlie lurked in a corner seat. He was a lily-white All-American boy who left his prestigious job at a corporate law firm to play cards. His wife, meanwhile, stayed home, wondering where everything went wrong. Other rounders -- doctors, bankers, computer programmers -- gathered around us, coming and going throughout the night.

I knew them well, but we normally did not all play at the same table. I was accustomed to seeing a smattering of slack-jawed garlic-eaters diluting the poker gene pool. But the suckers had vanished. In a city of 8.1 million people, we were part of a dwindling cadre of rounders -- currently only a few dozen -- who still played games bigger than $1/$2 in the underground clubs.

As midnight approached, we started adding columns of black chips to our stacks without necessarily paying for them beforehand. When someone suffered a bad beat, or even a well-deserved comeuppance, he would replace the missing towers.

Soon everyone began to straddle: $25 under the gun, $75 restraddle, $200 re-restraddle. Preflop raises came at $1,000. All this to steal $15 in blinds. One hand, I looked down to find 10-7 suited, so I promptly raised the $200 straddle from middle position to $1,000. Anon called from the big blind. Bob grimaced in pain, he wanted to call so bad. But he threw away his cards, letting me know that one of the remaining sevens, and probably a two, were out of play.

When the flop came 6-8-J rainbow, Bob looked disgusted. OK, he folded a six. I naturally bet out $1,500. Anon promptly called. I checked behind him when a king arrived on the turn. An ace fell on the river, and Anon thought long and hard before checking. "Missed," I grunted as I started to muck. But the wild look on Anon's face screamed that my 10 high might be good. Reluctantly, I flipped my cards up. And waited.

Anon sat motionless. During this interminable delay, I said a novena. Both to win the hand and arrive home safe.

My fears sprung not merely from a feverish mind. Underground games in Manhattan have become enormous, and dangerous.

On May 24, three men brandishing pistols rushed the door of a popular underground poker room in Manhattan. Wearing only sunglasses to mask their identity, they seized control of the room with the confidence of trained professionals.

This oddly was a relief. Last year, when the current spate of robberies started, thugs raided a nearby room. They had bigger guns, but apparently not nearly the same guts. One of the heavies was shaking so hard that the club's employees went out of their way to cooperate so he would calm down and not accidentally kill someone.

None of the rounders recognized the May 24 robbers as regular players. Nevertheless, the gunmen cut a beeline to the big game in the back of the room. Men who robbed poker clubs in New York historically left players alone and instead focused on the cage. This is where you would expect to find the money. Instead, this group went directly to the players at a $5/$10 no-limit game where the average stack was over $5,000. In menacing but controlled voices, they ordered the players to empty their pockets.

That this team of gunmen showed up on that particular night has spawned numerous rumors concerning their ties to the poker community. Because of the disappearance of many of the city's high-stakes no-limit players, the underground dens now stagger their games. This ensures that only a few high-stakes tables compete for players each night. Regulars have grown familiar with the weekly rotation. The big game at this club, however, usually formed on Tuesdays. You would have needed a well-informed insider to know beforehand that a scheduling glitch sited the big game there that Wednesday.

However they learned about this game, the thieves chose the right time. They took $60,000 in cash from the nine players sitting at that $5/$10 table. This was in addition to the over $50,000 in chips in play. The 10th player, who was in the bathroom, cowered on the toilet clutching $8,500 in cash. He was reportedly the only person that night who did not crap his pants. With the amount of cash on the tables, it's hardly surprising that we are in the midst of a robbing spree.

I was instantly awakened back to the $180,000 game when Anon smacked his palm against the table. He flung his cards face-down toward the dealer. "I knew it, I should have bet."

I still don't know what he had, but I'm almost sure it must have been 4-7. Anon would have reraised on the flop with 7-9 and probably moved all-in on the turn.

"Yes, you should have bet your seven-high, and good call with the gutshot on the flop," I guessed.

Ed could only grin at me in disbelief. Moments like this compelled him to leave wife and hearth every night.

Sitting on a mountain of chips, I found my out. Even though my instincts told me to leave, I decided I would play until morning, when the neighborhood came to life.

The game broke at 9:30 a.m., but only because the club rented space in an office building. Management did not want games running during business hours. I walked out to the crisp morning air with my sweat-stained shirt, reeking of cigarettes, stress and coffee breath. By that point, however, I was not worth mugging.

As I weaved my oily corpse past hordes of responsible businessmen in their fancy suits, smelling of soap and balanced family lives, I sensed that there were fundamental problems developing in the poker underground.

The presence of deep-stack games would normally evidence a thriving poker community. However, the current trend toward disproportionately large stacks in relation to the blinds is symptomatic of a broader breakdown in the underground economy.

Traditionally, underground cardrooms occupied a vital role in training players in expert cash game strategy. Like the old Texas gamblers before them, many of today's legends honed their skills in these clubs, particularly in New York City. Case in point: Howard Lederer may now be the Professor of Poker, but in the 1980s, he was just some homeless guy sleeping in Washington Square Park after repeatedly losing his entire bankroll to the city's infamous rounders.

Underground rooms serve an essential role in training the next generation of players, because casinos do not offer games that allow poker to be played the way it was intended, unless a player owns a bankroll to compete at the highest stakes.

Big corporations are too smart to allow players to lose their money quickly. Their profits flow from keeping players at the table. Casinos therefore enforce idiotic policies such as Bellagio's $300 maximum buy-in at the $2/$5 no-limit tables. After a respectable preflop raise and continuation bet, not many players will fold top pair, especially if they started with just $300. Forget the possibility of pushing anyone off even the most marginal hands.

Admittedly, many casinos remove caps for their bigger games. No cap buy-ins are common for $10/$25 or $25/$50 no-limit tables. But if you are playing these games, you are likely well up on the learning curve already. Outside of underground rooms, there is no place to learn the subtleties of the game unless you already have a large bankroll and are willing to play the biggest games.

Underground rooms used to offer midlevel games with sufficient buy-ins to allow for tactical maneuvering. Unlike the maximum buy-ins of 60 times to 100 times the big blind that prevail in most casinos, such rooms permitted players to buy in for at least 200 times.

These games are better for learning advanced plays because they allow for bluff reraises and check-raise steals without pot-committing opponents to calling. Moreover, when playing deep-stack poker, a player must learn quickly that an overpair is just not that great of a hand when facing several raises.

Underground clubs also supported a stable group of players who came to know each other's play in intimate detail. Such a community does not exist in a casino. This distinction is important because developing expert no-limit skills requires a player to cultivate a habit of observing very closely how people play.

It is simply not possible to determine in a few hours the true habits of other players, other than assigning broad categories such as tight, loose, aggressive, passive and maniac. Not enough hands are shown down in even a 10-hour session to form reliable determinations of how a player reacts to pressure or what hands he will raise out of position. This is particularly true if a player is good enough to introduce a minimal amount of randomness to his play.

Generally speaking, therefore, deep observational skills do not develop for casino players because the effort required to practice them is not as crucial as in the underground community. In contrast to casino players, underground rounders have a greater incentive to develop reliable kinesics intuition to maintain an edge over a stable population of competitors over the long term. The efforts to foster such aptitude, however, are underrewarded within the non-iterative environment of casinos. There, a player can skate along in blissful ignorance without perceptible disadvantage.

The trick is to foster midlevel games with sufficient buy-ins to allow for expert play, but to keep the games from growing so big that they squeeze out midlevel players. Underground rooms historically achieved this balance. Unfortunately, the dual pressures of police raids and armed robberies have amputated the poker pyramid. The middle layers necessary for building experience are vanishing. This threatens a larger breakdown within the poker community.

This decline all started with a few arrests.

From the 1980s through 2000, law enforcement generally left poker rooms alone. Two of the most famous from that era, the Diamond Club and The Mayfair Bridge Club, were famous proving grounds for such legends as Lederer, Erik Seidel, and Dan Harrington. The NYPD, however, closed the clubs in the summer of 2000 during the Giuliani administration's law and order campaign.

Underground rooms nevertheless flourished in New York. Up through the poker boom in 2003, several major clubs established themselves in Manhattan. The better known included Playstation near Union Square and Players' Club on the Upper West Side. Significant clubs also sprouted throughout the city. Despite a few sporadic raids, there was no concerted crackdown.

Vice squads from the NYPD fired the first salvo in the current campaign against the underground rooms on "Black Thursday," May 26, 2005. These crews shuttered numerous rooms, including Playstation and Players' Club. The authorities were shocked -- shocked -- to find gambling in those establishments, even though Playstation purportedly maintained an alarm wired directly to the local precinct. Police seized over $100,000 in cash and arrested dozens of employees.

Although these raids shook the underground poker scene, they still left its foundation intact. The surviving clubs voluntarily shut down for weeks, but reopened when the heat died down.

The rounders' outrage over the police crackdown grew so intense that they staged, in July 2005, a demonstration outside City Hall. Rounders viewed playing poker as a civil right in light of the history of underground rooms in New York, the lack of explicit statutory authority prohibiting such rooms, and even the link between poker, rugged individualism and Manifest Destiny.

Indeed, although this legal argument has never previously been raised, most forms of poker should be legal in New York. Penal Law Section 225.00(2) defines gambling as placing a wager on "the outcome of a contest of chance or a future contingent event not under his control or influence." Under this definition, the police raids themselves are illegal because most poker games fall outside the ambit of New York's statutory framework. A player can exercise "influence or control" over the flop, turn and river cards: He can bet enough so that they never happen.

The city responded to the rounders' demands on Oct. 14, 2005. At approximately 11:30 p.m., police stormed a major club near Chelsea. They seized over $60,000 in cash. The bust came down on the eve of a $100,000 tournament. The NYPD apparently missed the event because of mistaken information over its start date.

In January, the NYPD swooped down on the Hudson Club and Doubletake, the successor to Playstation. Particularly troubling about these raids was not only their timing -- which suggested an accelerating crackdown on poker rooms -- but also the unwarranted hostility displayed by the cops.

Up to and including the October 2005 raids, police reacted to the well-behaved order permeating underground rooms by treating the players with a modicum of respect. After all, it is not illegal to play poker in New York or frequent underground clubs. Even if Section 225 applied to poker, it is narrowly directed against owners of gambling establishments and their employees, and not against players. Reports of the January raids, however, reveal significant anger against cops who unnecessarily detained elderly players for hours and required them to seek permission to go to the bathroom or take prescription medicine.

In May, vice squads raided four of the remaining major clubs in Manhattan. An unprecedented degree of police hostility accompanied these arrests. Past raids were spearheaded by officers in windbreakers who entered the clubs with weapons holstered. During these recent raids, however, police in body armor stormed the rooms with guns drawn.

In one club, cops forced players to lie down on the floor with their hands on their heads. Only after some protests did they grant an exemption to a grandmother who had been playing a low-limit game. In another raid that same night, they isolated a petrified teenage waitress and threatened her with jail if she did not rat out the dealers.

This hostility did not always exist. Playstation reportedly had a direct line to the local precinct, and the Mayfair's employees wore medallions that summoned police in an emergency. (The Mayfair medallions were reportedly depicted by the rather ugly white necklace Famke Janssen wore in Rounders. In the movie, the Chesterfield was the Mayfair.)

Thugs now believe, probably correctly, that underground rooms cannot rely on cops for help during an emergency. Accordingly, an unforeseen consequence of the increasingly hostile police raids is that they have encouraged robberies. Together, these two factors have distorted the fundamental economy of the underground rooms.

The frequency of raids and robberies has relegated many recreational players to their homes or worse: Atlantic City. Only pros and very motivated players now regularly show up at the clubs. Such men are generally solid players who love to play big. This development has not only thinned the $2/$5 and $5/$10 no-limit population, but it has also starved the $1/$2 games that are the breeding ground of future $2/$5 players (and initial fodder for the $5/$10 game).

Although $2/$5 games still form, the concentration of sharks has skyrocketed, making the games play much bigger and tougher than usual. This has shunted many midlevel players to the $1/$2 tables and compelled rooms to cancel their $2/$5 no-limit games in favor of $5/$10. Midlimit players seeking experience, therefore, are left to choose either baby no-limit or deep-stack, $5/$10 no-limit.

At the same time, to reduce the risk of losing their stacks when police raid a room and seize all cash and chips as "evidence," many respected rounders now play on credit. Other players have made predeposits, generally up to $10,000, with the club owners so they do not have to bring cash to the rooms.

This way, if cops seize their chips, they only lose profits; because the clubs generally erase that evening's buy-ins from their books after a raid. Barring such force majeure, however, the understanding is players will settle up before leaving. But this is not always the case. Players now do not often carry sufficient cash to cover their buy-ins, and ATMs do not permit $10,000 withdrawals. Even in the case of predepositing rounders, club owners simply do not store the deposits on the premises.

After a particularly bad beat, players will often rebuy on credit for double their initial buy-in without having the funds on hand to cover. This creates a ratcheting upwards of table stakes. Because the $5/$10 no-limit games in underground clubs are usually uncapped, players now regularly buy in for $5,000 or higher without putting up cash.

Even the $1/$2 no-limit games, which are capped, play too high. In one popular $1/$2 game, where the maximum buy-in is $750, several players usually command over $4,000 in chips by late evening.

Playing on credit has led to the tendency for players not to be fully paid after a big win. That many clubs are asking players to extend them credit (because their losing players were unable to settle up for the evening) is causing players to demand more credit from the rooms, resulting in a vicious cycle. The easier the credit, the bigger the games, and the greater incentive for robberies.

While it remains uncertain whether this degeneration can be reversed, two trends deserve watching.

First is the rise of semi-private "home" games. Subcommunities of players have started organizing home games for a short list of vetted players. A typical $5/$10 semi-private game outside the city has an average buy-in of $5,000. Unfortunately, the rakes in these games are high, and the player pool is tiny. There are advantages to maintaining a small, collegiate community of players. But you also want sufficient elasticity in the pool so that fresh money and talent are constantly added. With the minuscule player pools in semi-private home games, the dangers of soft play engendered by close friendships are too great. Underground rooms used to offer a middle ground between incestuous private games and anonymous casinos.

Second is for rounders to organize semi-private games online. One site, Third Bullet Poker, markets itself as the "underground room online." It maintains a medium-sized pool of players with whom you can gain familiarity over the long term, just as rounders would in brick and mortar underground clubs.

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