Sidequests: Playing Pool in New York City

Author’s Note in the footnote.¹I always wanted to write about pool but I didn’t really know how. Should I write about how to play pool, like strategically? Or maybe why I enjoy the game itself? Do my readers even care, given this is a daytrading blog? Whatever. It’s my blog and I can do what I want. I’m just gonna first-person this shit and see where it goes.

For the last 15 years of my life, getting good at pool has been my number 1 sidequest. It’s not the main engine that drives my life like trading, but it can get close. I can really get into it. I can also leave it alone if I have other burning priorities like building a career or starting a family. I’ve had my ups and downs and overall and I’m nothing special but it’s been an enjoyable ride.

Early Days

I first started playing pool in the Mesa Court freshman dorms at UC Irvine. My dormmate got me into the game and then he started showing me old Efren Reyes highlights on Youtube.

From that, I witnessed sheer genius–a man who could shoot his way out of impossible positions. It painted the game of pool in a completely different light. It became *the beautiful game* that I wanted to master. I bought my own cue and a book titled “Ray Martin’s 99 Critical Shots of Pool”. There were lots of late nights where you could say I didn’t have my priorities in order.

Despite tons of investment in time and mental effort, I was just OK. UCI had a hobbyist club for us billiard fanatics called the Anteater Billiard Club–it was about 20ish players and there was a ranking based on 9-ball ladder matches and tournaments. I always hovered around 10th.²BTW it made me really sad to learn a couple years ago that the ABC is no more and the pool tables at the student center have been replaced with an E-Gaming Center. I did win a tournament once but it felt a bit lucky because my finals opponent kept choking on the 9-ball. As much as I loved the game, I had no delusions that I could go pro.

So that’s 2007-2009ish. From 2010 on, the trading bug replaced the pool bug. I would still play but it wasn’t an obsession anymore.

In 2011, I move to NYC and I take my cue with me. I’d play to pass the time but I wasn’t making any effort at it. I had to invest all my time into being good at making money so I could pay my rent and such.

Couple years later, I found myself practicing alone at Brownstone Billiards out in Brooklyn and then out of nowhere, this huge black guy approaches me. With a warm smile and a gentle, high pitched voice that absolutely does not match his body, he asks…

Ok sure. Why not? He introduces himself as Serge. Once I spot his warm-up strokes, I knew that I had no chance. I see his big mitts creating these small, dainty little micro movements like a skilled violinist. He pockets balls with a gentle touch and takes me to school in 9-ball, winning 8 games total to my 1. Luckily we didn’t play for any money. As we unscrew our cues, he asks if I want to join his 8-ball team at Amsterdam Billiards. He thinks I have some potential. Having not built much of a social life in NYC at that point besides happy hours with other traders, I agree to join.

My first pool league, sounds like a cool and fun time. I’d walk into Amsterdam and I’d see the painted portrait of Jeanette “The Black Widow” Lee. There’s former world champion Mika Immonen practicing on the pro table. Real pool being played here–it’s nice.

League was not what I expected. Serge captains the team–he recruits the players, organizes all the team practices, checks for who’s in/out for the week, and keeps score for matches–standard stuff. What was beyond standard was that he would micro-manage all our games. While the opponent was at the table, he’d be in our ear hashing out table scenarios and finding the easiest path to victory.

Clustered table? “Go safe and bunt the cueball softly, and leave him an angle where he breaks out your cluster. He’ll take the bait.”

Open table with potential ball in hand? “If he fouls, go 3 ball top left, 4 ball side, and then stop shot on 6 bottom corner to leave it for the 8. That’s your pattern to get out.“

And to some, that might sound annoying but for us, that was a massive strategy boost because he knew the game better than all of us. We’d always use our timeouts for him to coach us on a high leverage shot. Being on Serge’s high-intensity team appealed to my “try-hard-to-be-good-at-shit” nature.³some teams were more chill and just wanted to drink and shoot. some teams were more competitive but did unethical shit like sandbagging where you tank games to keep a low handicap. I liked that we were a competitive team that always played hard and didn’t resort to scumbaggery I never argued with Serge and I just tried to soak up all his experience. He didn’t tolerate fools much. Make questionable decisions and he’d ask why you fucked around. Do it too often and he’d cut you from the team. Serge’s coaching completely changed how I understood the game of 8-Ball. It was far more tactically nuanced than I had ever known. Here are the 3 main lessons I learned about winning at 8-Ball aka “Stripes and Solids”:

1. The game isn’t over until the eight-ball is in. Shooting your own balls in doesn’t win the game or even necessarily increase your chances of winning the game. It’s table control that increases win probability.
2. Plan the run-out pattern that you can execute to win the game. If that pattern doesn’t yet exist, then develop the run-out pattern⁴(moving around the balls to create openings). If you aren’t skilled enough to develop it, stall the game with pure defense and induce an opponent error.
3. A defensive shot that nets ball-in-hand⁵under pro-style rules, the penalty for a foul is “ball in hand” where the opponent can place the cue ball anywhere on the table. this is different from common “bar rules” where the cue ball can only be placed behind the breaking line is more valuable than making a tough shot.

Learning to play tactically is what separates a Bar Player Billy from a Pool Hall Harry. I’ve played at least 300 different people in pool since moving to NYC and I’ll describe it as such: There are non-players⁶(people who only play socially and don’t know the proper rules or how to make a ball) and there are pool players⁷(someone who, when asked what their hobbies are, would answer pool at some point) and of the pool players, you can roughly divide them into Billy’s or Harry’s.

Bar Player Billy

• Usual hangout: a bar with coin-operated tables and barely any space to play
• Most common opponents: his friends (typically non-players), bar regulars, APA league players
• Primary thought at the table: “let’s shoot a ball in.”
• One-speed shooter–either smashing it in or only pocket speed for almost every shot
• Only knows how to play 8-ball, maybe tried 9 here and there
• 1/3rd of all Billy’s own their own cue
• Enjoys social aspect of pool, may or may not have ambitions to improve
• Some harbor weird beliefs like “you’re not a real man if you use the mechanical bridge”

Pool Hall Harry

• Usual hangout: dedicated pool halls with full sized tables
• Most common opponents: pool hall regulars, league and tournament opponents, gamblers, anyone who knows what a FargoRate is
• Primary thought at the table: “how do I win the game?”
• Multi-speed shooter–shot speed varies based on what is needed for proper cue ball position
• Knows how to play multiple games — 8/9/10-ball/straight pool/1 pocket/3-cushion/etc.
• Every single Harry owns his own cue, 1/3rd own multiple cues like a break cue or jump cue
• Enjoys studying the game and improving via solo practice
• Some harbor weird beliefs like “jump cues/soft breaks/template racks ought to be banned from tournaments”

There’s a whole spiel I could go on about the Dunning-Kruger effect when a Billy evolves into a Harry. The more he learns, the less he realizes he knows. Their self-image as a player goes from “best player out of all my friends” to “just another mook” the minute they stroll into a serious billiards parlor and see a shortstop⁸shortstop is pool terminology for a highly skilled non-pro player hammer a 4-rail stun shot into the heart of the pocket for perfect position.

I start off as a 4 handicap in league play. It’s the default handicap until there’s more data on your skill. For the unfamiliar, almost all amateur pool leagues in the U.S. are handicapped so that players of all levels can participate. Higher handicap ratings imply greater skill and higher handicap players need to win more racks to secure a head-to-head win. Being 1 rank higher usually means needing to win 1 extra game over an opponent to win the heads-up match⁹(it’s determined by what we call “race to X”, meaning first player to win X amount wins the match), 2 ranks higher = 2 more games, etc. If a 4 plays another 4 and the first player to win 5 racks takes it home–it’s called a 5-5 race. If a 4 plays a 7, the 7 needs to win three more racks so it’s an 8-5 race. For our league, the handicap scale ranged from 2 to 8.¹⁰By the way, being an 8 does not mean pro level or even close, it means a high level amateur 8-ball player relative to that local area. Anyone who is so good they would still win all their matches as an 8 should probably advance to playing pre-dominantly nine and ten ball. The league director determines each individual handicap by looking at score sheets and eye-balling players in live action.

Even though a lower handicap gives the team an advantage in terms of requiring less racks to win, I wanted to attain a higher handicap for my own sake as a badge of skill.

Here’s a rough guide for the non-pool players to get some context:

You might play a little pool yourself but think “nah I could never play in a league, I’d miss easy shots and get smoked” and I’m here to say: you’d be TOTALLY WRONG. There are plenty of beginners in every league who miss basic shots and you could slot in as a 2 or 3 without anyone blinking. Some of these types are even big assets to their team if they can learn crafty play.¹¹safety play and table management, which are pool-IQ based abilities you can learn without necessarily improving your ability to pot balls

Your archetypical Billy who beats down the random drunks at the pub? He’s usually a 4. If he struggles under pressure, the league director might drop him to 3. If he’s got talent, he can get to 5 even without knowing the finer nuances of 8-Ball. Those are the aggressive runner types who, unwisely, feel compelled to run every rack out no matter the probabilities… but can actually do it on a good night.¹²these types never have the best records despite their talent because they often have as many bad losses as they have amazing wins. Low pool IQ is why they’re still a 5.

Once you get to 6 and higher, it’s almost entirely Harry types–people who have played for many years and have studied the game. It’s not casual for them anymore, they want to shoot well and win. This isn’t to say there aren’t Harry’s who rate lower. There’s a type of Harry who often leans very defensive to win games but their growth has long been hindered by shakey fundamentals–such as an awkward stance, excessive body movement, crooked arm action, or actual legal blindness. They know the game well but they’re 50-50 to pot a straight shot longer than 5 feet. Some have been league regulars for 20 years… but still rate as 4’s. That’s like my worst nightmare.

My first foray into the NYC league pool scene lasted about half a year. I was a solid 4 with more wins than losses, but I had one painful weakness: extreme slowness. I took forever to shoot.

I got warned several times to speed up and then one day before a new season started, Serge decided he didn’t want to deal with my bullshit anymore. He cut me.

“You’re a good listener Pete and I hate to do this but you’re out. You’re killing us. Come back when you’re faster. “ — Serge over text. I’m not gonna lie, that really hurt and it made me want to cry.

Why was I so slow? A combination of social anxiety and analysis paralysis at the table. Let’s start with the social anxiety–people watching me play makes me nervous and I don’t know to handle my shit other than to stand there waiting until my heart rate slows down¹³and I know what you’re thinking…but alcohol didn’t help. Then when I’m in the shooting process itself, I got stuck pondering too many potential choices. Once I learned about shot selection and defense in eight-ball¹⁴(as a 9-ball player in college, all I did was think about how to shoot the lowest ball and get to the next ball—way more simple), it felt like I had to evaluate 20 different decisions at the table. Should I play safety or go for the run out? Should I shoot the 5 first and the 4 second? Should I shoot the 3 first and the 4 second? Should I shoot it with draw or stun? Should I get off my shot line and double check the cueball’s tangent line with my thumb and index finger, for the third time? It felt wrong to rush myself and do something stupid to lose the game, So, yeah, I was in my own head a lot and awful with my pace. I bet everyone hated me but was just too nice to say it. I stopped playing.

The Prince of 200 Water Street

Fast forward 2 years to 2015. We¹⁵me, my Chinese stock broker roommate and his girlfriend, and my African roommate have to move to a new apartment because we were refused a lease renewal for a dumb reason. Allegedly, my roommate’s dog bit the leasing lady. He claims it’s a fabrication to kick us out so mgmt can jack up the price for the next tenant. Having played with his dog, a friendly mixed lab, I lean towards believing him.¹⁶Years later, I would learn my roommate is a bit of a liar. He also got me into my best private investment ever and my worst private investment ever–a story another time. My other roommate manages to find us a sweet new 2-bedroom at 200 Water St, a luxury apartment complex right next to the South Street Seaport. Once again, they take the 2 bedrooms and they stick me with the living room with a bookshelf wall divider. But on the plus side, 200 Water has an awesome pool table on the sixth floor common lounge.

I start playing a little bit, screwing around. Then I’m there every day. Then I’m there all night working on my game until they kick me out. I’d just be hitting shot after shot, feeling unsatisfied with the result or even just the ‘feeling’ of the shot, and then I’d stay longer than I anticipated to keep ironing it out. I hyperfocused on my fundamentals, which I divided into alignment (aiming) and stroke (cue ball contact). By this time, the Youtube instructional billiards sphere was far deeper than what it was in 2007 or 2013. I would watch videos from Tor Lowry or Dr. Dave Billiards and try to emulate every single pro tip¹⁷other channels I like: Sharivari, Niels Feijen, Jasmine Ouschan. I became a student of the technique of hitting the cueball goooood. I can’t tell you how many hours were poured into just being able to hit a draw shot (backspin).

200 Water, often bustling with energetic outgoing residents, was the perfect home for a young 20’s NYC professional looking to make connections. People would hold parties in the lounge or they’d be coming back from a long night out to unwind. I must have played 100 different people and encountered all kinds of characters just by agreeing to share the table and play pool with them.

I’d play with fratboys and finance bro’s, classic Bar Table Billy types, who thought they knew how to shoot until I steam rolled them. Then they’d practically form a line to be the first guy to beat me. We’d banter and they’d offer me a beer and I’d instantly be one of the guys just from pool skill.

Then there was this older 75-year old gentleman, Jack, one of the few seniors in the building but he loved to hang out with younger people. I probably played him the most. Even though he hated modern pool rules¹⁸ball in hand was blasphemy to him but he tolerated my insistence on it, he treated me like a son when I played with him–always gassing me up on my best shots and nicknaming me “Pete the Killer” and then telling me for the 25th time that it’s a Goodfellas reference.

Oh and the women… so many cute women–models, fashion industry types, artists, students–always coming in. I became pool buds with this polished sales guy, Robb, who oozed charisma and would bring scores of gorgeous models to the lounge on Friday evenings¹⁹Robb worked in door-to-door MLM sales and he said these model gatherings was work related for him. I didn’t really understand and didn’t care to and if I was there, he never turned down a chance to play me.²⁰I later learned that Robb grew up in rural in-land California–a hicktown of less than 60,000 people. Get this–at age 18, he shot a dude in the head over a stolen digital camera. Then he beat the murder charge and did a few years for manslaughter. Then I guess he reinvents himself into a playboy and slick-ass salesbro in NYC–like a story right out of a movie, what the fuck?!

He proposed mixed doubles to get the girls involved and then I’d be teaching an aspiring fashion model how to shoot while she awkwardly tried to form a stance in high heels. It was great. I had also made friends with these two Brazilian models by coaching them at pool and one day I saw them heading to the lounge with this ripped seven foot behemoth of a man, right when I was leaving. His distinct manbun and craggly beard looked familiar. 30 seconds later out the door, I realized it was New York Knicks center Joakim Noah. That could’ve been a great story if I just had stuck around a minute longer. The access you can get in NYC is wild.

The 200 Water experience helped a ton with social anxiety-related nerves. When you’re a pool player with your own stick and solo-practicing, there’s like this weird expectation when non-players approach you.

OMG this guy has his own cue. Are you good?! You must be good. You must be a hustler who gambles and wins lots of money. I bet you know all these trick shots.

These thoughts got in my head and actually made me nervous to just play random people who couldn’t shoot at all because I didn’t want to disappoint anyone’s expectation. Somehow I learned to deal with it. To cope with the social anxiety, I focused more on blending in versus trying to win. I learned to loosen up and to try to make people feel like they’re playing a chill, humble dude and not at all the hypercompetitive try-hard that I actually am. I’d fill up pockets of silence by asking them about their life or I’d make a self-deprecating remark after a mistake. Only a donkey like me can hook myself that bad! If someone took a questionable shot, I’d tell them what I would have done if I thought they were receptive to advice. I shot faster and avoided overthinking. I’d take on aggressive pots to impress crowds. Familiar faces would walk in, pick up a cue, and point at me–“Rack ’em up Pete, I’m finally going to beat you today!” My self-image improved big-time–people knew me as *the pool player* and I felt like the prince of the building. Little did anyone know that if we all set foot in a real outfit full of Harry’s shooting big league pool, I would be exposed as a total nobody.

The Comeback

With a renewed love for the game, I decide it’s time to get back to playing the people who can actually challenge me. I send Serge a text that I want back in. I then politely demonstrate to him over a few games that I’m not a slow-ass piece of shit anymore.

The first season back, I’m aces. I go 9-1 in my first 10 matches, 13-2 overall for the season. I wasn’t the best player on the team by any means but arguably the most valuable in a “pound for pound” sense because I played so far above my weight. Winning in pool leagues isn’t about total skill, it’s about playing above your handicap. The league director Tony Robles²¹at the time the Amsterdam Billiards house pro and a former Mosconi Cup winner and a totally awesome guy personally congratulates me on such rapid improvement and he bumps my handicap up to a 5. I feel like the sky is the limit and the game is again completely consuming me.

I would continue to win 70-80% of my games as a 5. Within another two seasons, I would get raised to 6. I have developed both offense and defense. I can play crafty when behind and I can run out when the opening presents itself. I also play well under pressure and win all of my playoff matches. We win our first team championship in the summer of 2016. I still have the trophy.

Next season rolls out and I start off hot at 8-0. I am dead certain I’m going to be a 7 any moment now–that’s Serge’s handicap and the league only has a dozen or so players at that rank or higher. It’s reserved for players who can really shoot the lights out. I even join the Amsterdam 9-ball league to start competing with the big boys. Meanwhile, our 8-ball team stays in first place all year and we reach the finals with a chance to repeat as back to back champions. In the finals, one of my teammates takes an L and we start off behind 0-1. Serge marks the scoresheet, looks at me, and declares “We can’t go down 0-2, we need this win. Pete you’re up.”

I’m brimming with confidence–get on my back everyone, I got this!

And… that’s my peak. I wouldn’t have believed you if you told me at the time it but that was the peak.

With all the marbles on the line, I play like absolute dog water. Shot just never felt right from the getgo and it got uglier as the match went on. I shit all over myself in the pressure moments. I lose the match and our team loses the championship by a score of 3-1.

The loss stings but I keep practicing as hard as ever, convinced that it was just a one-off bad week. It happens, whatever, shake it off right?

Well, reality can punch harder than you think. Your game hits a wall and it lasts so much longer than you could ever imagine. I did not become a 7 the next season like I thought I would. In fact…

My game would go on such a freefall that in the middle of the season, Tony downgraded me to 5 out of pity. I suck again.

Every week, the L’s and the immeasurable disappointment kept accumulating. Anyone watching me could see I was playing with a dark raincloud over my head. I kept thinking about how well I played to get to a 6 level and I kept chasing it every match–trying to make tough shots and remind myself I was still good. Then I’d flub the easy shots, feel this raging tilt wanting to burst out, and I’d lash out like an angry clown–slamming my stick and cussing until the whole room heard me. Totally embarassing.

Confidence can swiftly morph into self-doubt, transforming you into an obsession-driven monster. During every practice, if I hit a few bad shots, I’d spiral into panic mode, overanalyzing my shot mechanics to eliminate whatever sneaky flaw had crept in, which only exacerbated the inconsistencies. Golfers would say that I had too many “swing thoughts”.

Oh I know the solution all along. I’ll twist at the waist to get lower and eye ball the shot like the snooker pros do.

No, no, no–the key to unlock your old stroke again has been higher elbow placement.

I’m chicken-winging at impact and that’s the worst thing imaginable. That’s how 4’s stay 4’s for 20 years. STOP DOING THAT!!!²²free advice: if you practice at anything athletic, replace “don’t do this” type thoughts with “do (what I actually want to do)” thoughts

It’d be 1AM and I’d get out of my bed because I can’t sleep after a poor match. I’d be holding my cue over my kitchen table, going over different grips, different bridges, different warm-up strokes. Yeah… that’ll fix everything…

Pool became a disjointed list of instructions in my head rather than just letting myself play. Nothing seemed to work long-term and I stopped enjoying the game. The 9-ball league wasn’t any better–those guys would totally outclass me and send me on the subway ride home feeling like the world’s biggest fraud. I guess I really am just an uncoordinated buffoon who can’t develop long-term skill in this game. After that season, now around 2017, I threw in the towel and quit both leagues. Time for a break.

Second Comeback

I thought I’d focus on other things and revisit pool later, definitely not any longer than one season… which became two seasons. Then a year. Then two and then three…

Now it’s 2020… almost a decade since I moved to NYC.

I felt that itch again. I started to practice more regularly at the lounge table of our Brooklyn apartment. It wasn’t as good a table as the 200 Water table but that era had ended a couple years back when my roommate abruptly stopped paying rent and forced everyone to go their own way. Now I’m a married man with no kids and plenty of time for a hobby. It’s finally time to make another comeback.

Oops, here comes a generational pandemic and now every pool hall in the five boroughs is shut down until further notice. What can you do?

To be continued.