Born to Gamble Part IV: Ramblin' Man

When Senor moved to New York City in the mid-1990s, all hell broke loose. He's Neal Cassady to my Jack Kerouac. He's Oscar Acosta to my Hunter Thompson. He's Lenny to my Carl. Although we were fraternity brothers from the same pledge class, we weren't close friends and were in different circles during college. That changed when he left chiropractor school in Atlanta and moved to Manhattan after his hand modeling career faltered.

I had just walked out of my job on Wall Street and started writing my first ever novel (that would remain unfinished to this day). I found a job as the manager of an adult video and novelty store called the Booty Shack located on the Queens and Long Island border. By days, I sold German pissing videos and purple dildos to sexually adventurous New Yorkers. By night, Senor and I were partying it up hard drinking heavily at bars in Murray Hill and trying to pick up horny chicks in AOL chat rooms.

We went on a lot of trips together. When you travel with other people, it's important that your personalities mesh otherwise you're doomed to have an ugly trip. Senor and I got along extremely well, and that's why we've traveled together over all these years. We're both self-sufficient and easy going, willing to do anything at any given point, yet disciplined enough that we would stick to a schedule and itinerary. We were both travelers and not tourists and always took that attitude with us no matter where we went.

We took an amazing trip to Europe and you can imagine the trouble we got into during my first ever visit to Amsterdam. The events of one night were captured in a story called Shooting Pool, which involves a pair of underaged French girls. Here's an excerpt...

Amsterdam
7 Aug 96

I was kicked out of the Holland Casino for a dress code violation. The Euro-trash uppercrust take their casinos seriously. My attire failed to meet the minimum specifications: clean dress shoes, pants, collared shirt, and a jacket and tie. After a quick glance at the patrons inside I realized that most of the men were well groomed and they were all wearing tuxedos. It was scene right out of a James Bond movie and there I stood at the entrance trying to get in, decked out in Birkenstocks, ripped jeans, and a NY Knicks T-shirt. It didn't help that I had been tripping on mushrooms for most of the night, and I decided the best thing to do before I came down was to play a few hands of blackjack, and maybe even find a poker game to sit in on... but I couldn't even get in the front door... More

That story is one of several thousand odd nights that I experienced with Senor. Shooting Pool summed up the kind of hijinks that we would get into on our trips. I used to send out an e-mail newsletter to our friends about our latest "misadventures" and at some point I would write something like, "It wasn't until the plane safely landed after skidding a hundred yards on the slick runway when Senor sheepishly mentioned to me that he was flying without pilot's license and dropped out of flight school after the first week."

No matter if it was Amsterdam, NYC, or New Orleans... we pushed ourselves to the limits of sanity and sobriety and back again. If there was anyone that I knew who enjoyed living in the moment more than me... it was Senor.

And we gambled too. We'd bet on college basketball and pro football through bookies. We'd also play the occasional poker home game at my apartment in Park Slope. We started going to the Connecticut casinos when Foxwoods and Mohegan Sun opened up. Senor's parents lived in Connecticut and we'd take the train to the burbs, then pick up his car to drive to the casino. We'd play blackjack all night and get stoned in the parking deck while Senor would do his $100 bet trick when he'd walk up to any table game, whether it was roulette, craps, or blackjack and bet a single $100 bet. If he won, he was up $200. He'd bet a Ben Franklin on Red or the Pass Line or play a hand of blackjack. And that's how Senor rolled...

It was at that point in our mid-20s where we raised the stakes that we'd gamble with. Instead of money, we began testing the limits of ourselves and our bodies and gambled with our lives. In many ways that sentence sounds more dramatic than it was because at the time we were just living and living on the edge was all that I knew. But the more I think about what we did in the 1990s, the more I realized how lucky we were that we never ended up dead or in jail. We managed to avoid hospitals and court rooms as I began to rack up material for a five or six novels.

We stayed up for days at a time partying and lived for a few years as functioning addicts. I dunno how Senor held down an 8-5 office job in Midtown, but he did and always showed up no matter how many doses of acid we took the night before or how late we were out drinking with NYU girls. My job didn't matter as much. As manager of the Booty Shack part of the job requirement was for me to be completely wasted on duty. I could go on and on about that time in my life... but then you wouldn't buy the book.

I gambled pretty heavily on the March Madness tournament every year. That's how I made the bulk of my income. If I won big, I'd have a fun summer and use my winnings to travel to some place exotic with Senor or see a bunch of concerts or go to Jazz Fest in New Orleans. If I lost, it was going to be a boring summer in the city while I sold anal lube to bored Long Island housewives and wrote pretentious poetry in my spiraled notebooks.

At some point I met a green and orange haired Suicide Girl named Zoe and moved out to Seattle to live with her. Getting to Seattle was another one of Senor and mine's epic misadventures. It started with me going out to the middle of Pennsy-tucky to visit Derek who just graduated college. He was friends with a non-pot-smoking Jamaican guy who was an ex-Army sergeant and worked as a prison guard at Lewisberg Federal Penitentiary. That's where the 1993 WTC bombers are held.

Anyway, Derek's friend fixed up cars and sold me a 1984 Chrysler Le Baron that I purchased with my March Madness winnings. It was a non-convertible and we joked that it was "Jon Voight's car" from that episode of Seinfeld when George though he bought the actor's used car. The car didn't have a working stereo and the AC sucked camel balls. But we made due and drove all the way from NYC to Seattle. We'd have the windows down most of the time and whoever rode shotgun held a mini boom box which was our only entertainment. We played every Grateful Dead bootleg in my collection as we visited friends in different cities along the way.

We got drunk and snuck into the fifth row at a Cubs game at Wrigley field in Chicago. We tried to pick up girls from the local high school volleyball team in Kearney, Nebraska. We played hackey sack in the end zone of Folsom Field in Boulder, Colorado. We ate mushrooms in Laramie, Wyoming. We almost broke down in Jackson Hole and had to spend the night. Senor got into a fight with a bouncer at a cowboy bar across the street from out motel. We got thrown out and were lucky to leave Wyoming with only a few scrapes.

We headed through majestic Idaho and wide open Montana before we got to Spokane. We spent the night in Spokane. There was a dentist's wife who lived nearby that I used to have phone sex with from time to time. I met her in a Motel 6 on the shady side of town, while Senor rented the room next door and ordered two escorts from the phone book. A mutual friend of ours would constantly order two girls at a time in NYC. He'd pick the better looking of the two and send the ugly one home. Sometimes he paid for both. So there we were, on a random Tuesday night in Spokane in $49 motel rooms, and letting our sexual deviancy loose like an undisciplined pit bull running around in a playground.

When we got to Seattle, Senor flew home and that's when things took a turn for the worse. One of the reasons I moved to Seattle was to be with Zoe, but that didn't work out. I think I was with her less than a week before we decided we made a huge mistake. She moved back to Bellingham while I stuck around Seattle. I could have gone back to NYC but I decided to stay. All I can remember about her was the pyramid of cigarette butts in her ashtray. She wore purple lipstick and the ends of the smashed butts would have a ring of purple on the edges.

Years later I realized that I knew that relationship was doomed and never going to work but I needed an excuse to leave NYC and Zoe was my out. That was a huge gamble to move to a city on the opposite coast where I only knew one person (my buddy from college Slinger) and I didn't have a place to live, nor a job. In those circumstances, you do your most living... when you say "Fuck it!" and move all your shit to some place completely different. That's when you find out what type of person you really are. I've always been independent and resourceful. And those attributes were put to the test. Luckily, I found a place to live within two days near the University of Washington and within a week I had two jobs.

"You reached the end of the line," Slinger would say about Seattle.

He was an East Coaster like myself and if anyone ever moved from East to West they understand the subtle and abrupt differences in mentalities from living in an East coast city like Boston or NYC, to living in a place like Seattle, which was more a small town that exploded into a huge city. I had a tough time adjusting to dealing with the West Coast flakiness at first, but after I got used to that way of living, I began to love living there, despite the rain. And it rained a shitload. When I moved there during the early summer, there was zero precipitation with bright blue skies and you could see Mt. Rainer from any spot in the city. Then one day in September it started raining and didn't stop for ten months.

My two years in Seattle were vital for my personal development as a person and writer. I had to leave familiar surroundings and do my own thing for a period of time while I sculpted my voice as a writer and I explored myself creatively unfettered from the criticism of my peers and without any of the prejudice and negativity that my family bombarded me with after I left Wall Street. I guess in their eyes, I flipped out. I graduated from a good college, walked out of a perfect and high paying job, stopped shaving, grew out my hair and worked in a porn shop before I moved out to the Pacific Northwest which is the serial murder capital of Western Civilization.

I was the hardest working slacker in Seattle in 1998. I held four jobs and I humped two crappy hourly wage positions. I had been making six figures on Wall Street and I gave it up for the Bohemian lifestyle. And yes, my bed was a mattress thrown into the corner of my room that I bought off a guy named Crackhead Stu for $20.

I read a ton of books and people whom I worked found out I was a writer and they would give me books. I never had a shortage of reading material and I discovered a couple of writers that I never read before like Chuck Palahniuk, Carlos Castaneda, Alan Watts, Joseph Campbell, David Sedaris, and Philip Roth.

Most of the time I sat on a huge couch scarred with burn holes on my porch with my housemates. We'd make fun of the sorority girls jogging by and watched the steady rain while we chain smoked and elicit sympathy from one another about our depressing childhoods and hopeless futures. Sometimes the rants would be politically driven. Slackers and hippies had opinions on everything including the government's coverup of UFOs and widespread usage of mind-control drugs. We'd share our disdain and scorn for the suits in Hollyweird or the fucktards that ran the major music labels. They were both guilty of ignoring originality.

Sometimes we'd drink micro-brews, pop too many pills, and play really bad music in the basement of our house until sunrise trying to become the postmodern reincarnation of the Velvet Underground. But that never happened because we were unmotivated ganja smoking wanna-be musicians and the melodies reverberating from my guitar sounded more like two frogs dry-humping each other on a squeaky stairway.

I also drank exclusively at the Blue Moon Tavern a few blocks from my house which had been frequented by other literary greats such as Ken Kesey and Allen Ginsberg. I hoped that by pissing in the same urinals that they pissed in and by sitting on the same bar stools that they sat in would miraculously make me a better writer. Tom Robbins described the Blue Moon as "a frenzy of distorted joy spinning just outside the reach of bourgeois horrors."

That summed up my time in Seattle.

I focused on writing and spent hours and hours every week holed up on my room sending off articles for submission in various literary magazines. Everything was rejected and I started hanging up my rejection letters on my wall, so when I left my room everyday to go out into the real world, I was reminded that I was a failure and that my biggest priority of that day was to improve my writing skills. After a while I stopped hanging up the rejection form letters because there was no more room left to hang them.

My buddy Slinger and I decided to write a screenplay together and for five or six months, we were diligent. He waited tables downtown and I'd come by after work to see what he wrote and I'd give him my pages. We both had no idea what we were doing and we spent most of the time drinking beer and smoking weed while discussing the screenplay with the Marnier's game on in the background. We never finished the script because Slinger got a job as a beat writer for a small newspaper in Florida and left Seattle. That screenplay became one of forty projects that I began in the 1990s and never finished.

During March Madness I opened up an account with a sports book on the island of Curacao. I funded it through Western Union and got a 100% deposit bonus. My buddies would place smaller bets using my account. After the second day, we were all broke. We had to fund my account three more times before the tournament ended. We all lost heavily that year but it was a lot of fun despite the fact we were complete degenerates.

The first time I ever played Texas Hold'em was in Bellingham when Slinger took me to the Nooksack Casino. We called it the "Nut Sack" and Slinger used to play there when he lived in Bellingham with Dutch a few years earlier. Dutch was the same guy who used the infamous "Dutch Bucks" in Jerry's homegame in Atlanta. Slinger and Dutch would play Hold'em there everyday after work. Slinger even won a few tournaments there. They quickly got me hooked on the two card poker game.

In Seattle, we occasionally played cards at Slinger's apartment with his roommate Ty who worked at a swanky bar and restaurant downtown. Some of Ty's co-workers lived in a house in Fremont and they held a home game every Monday. On the West Coast, Monday Night Football started at 6pm and that year they began it at 8pm EST or 5pm PCT. So the home game would start at halftime in the kitchen of the Trout House. They nicknamed it the Trout House because several members of the acid-jazz band Kilgore Trout lived there. They would practice in the basement and we could hear them during the games. When practice was over, the guitar and sax player would sit in and play with us.

We'd drink Labatt's, smoke weed, listen to great music, and tell dirty jokes. In short, we had a blast and since I worked weekends and had Mondays off... it was the one day of the week I couldn't wait for. The games at the Trout House were some of my favorite home games of all-time because everyone who played in it was pretty cool and we didn't mind losing money to one another. Mostly everyone had dead-end jobs either as line cooks or bartenders or waitstaff which meant everyone had cash to play.

We had some good players and the games were dealer's choice. We'd buy in $20 or $40 to start and it would not be uncommon to rebuy a few times. We played a lot of Stud and I introduced a game called 75 Cent Mexican, which is a variation of Midnight Baseball or No Peak. Ante was 75 cents (which was 3x the normal ante) and each player got dealt seven cards but you cannot look at them. 3s and 9s are wild, you can buy a card if for 75 cents if you have a 4. You turn the cards one at a time and have to beat the hand of the player showing. If Ty turned over a Queen to start, I'd have to keep turning over cards until I can beat his Queen. Let's say I have an 8 then a 9, then I'd have a pair of 8s and Slinger would have to turn over his cards one by one until he can beat that hand and so forth. You bet after a player makes a hand and these pots would swell up. It was the highlight of the games and I became a legend at the Trout House for creating the action game 75 Cent Mexican. The guys in the band loved the game so much, that they wrote a song with that title.

In 1998, the film Rounders came out and I saw it three times at the Neptune Theater in Seattle. We introduced Hold'em to our homegame and at first we kept making mistakes on what cards to burn. Yeah we were total rookies, but we thought Rounders was the greatest movie in the history of cinema. Little did I know that the film would affect millions of other poker junkies around the world.

Later that year, Phish played two monster concerts in Las Vegas including one on Halloween when they covered the entire Velvet Underground album Loaded. As soon as the shows were announced, Senor and I both knew we were going. I actually began my Las Vegas book with that scene. What you are about to read has not been seen by anyone, except my assistant Jessica who helped edit the manuscript for me. Enjoy the teaser of the first three paragraphs of my Las Vegas book...

Sometimes you get lucky before you even set foot on a plane bound for Las Vegas. I should have been arrested on the spot at Sea-Tac airport. Instead, I talked my way out of fines and imprisonment. More importantly, I avoided a huge legal tab from a over-priced criminal attorney wearing an off-the-rack suit whose sole job would be to try to find loopholes in my multiple drug possession charges. Sure, my good friend Senor was a high priced attorney in New York City but he had no juice on the left coast. All he could do was pick up the phone and hope that he could find a former law school chum in the greater Seattle area who owed him a favor. Otherwise, I'd be fucked. Properly.

1998. I was a long-haired cynic living in the slacker life Seattle trying to write screenplays while I smoked too much pot, slept with bored housewives from Vashon Island, and sat in bars listening to rambling dissertations from too many West Coast philosopher types, many of which I considered my close friends. That was back in a time way before airports took security seriously and you could travel with a horde of drugs on your person and not think twice about taking the risk. I had an ounce of high grade marijuana in my left pocket. In my right, a half an ounce of magic mushrooms was concealed. My sole job on that particular mission was to bring as many drugs as I could down from Seattle to Las Vegas.

My small backpack was filled with a long sleeve shirt, a Hawaiian shirt, two pairs of underwear, socks, my notebook, two pens, a Spalding Gray book and my toiletries bag. With memories of Billy Hayes stuck in a Turkish Prison from Midnight Express bouncing around my head, I double wrapped the drugs in Ziplock baggies. The mushrooms were small and odorless. That package was about the size of my wallet which I shoved into my front right pocket along with my wallet. The pot reeked. Badly. The more pot stinks, the better it is. I did my best to conceal the smell of some of the best shit I smoked in over a year. That package was about the size of a John Grisham novel. I wore cargo pants and it fit perfectly into one of those enlarged pockets.

As I walked through the metal detector, a guard who looked like Cheech Marin stopped me when the buzzer went off...

... to be continued


Editor's Note: If you have not read the first three installments, then visit... Born to Gamble Part 1: Where It All Begins and Born to Gamble Part 2: Southbound and Born to Gamble Part 3: Midnight Rambler. The fifth installment will be published later this week.