When I first moved to NYC in the mid-nineties I spent most of my social time with a friend/co-worker named Tyler. While my personality tends to be a bit cautious, Tyler has always been a genuinely warm and open person. A guy. This easygoing nature caused him to attract all sorts of strange and interesting (and sometimes intolerable) characters back then, many of whom I adopted by proxy. One of the more fascinating people who orbited my life back then was a guy Tyler and I very casually referred to as ‘Crazy Phil.’ I honestly don’t remember ever calling him anything else, because his eccentricity was so completely naked it naturally dominated and defined him. When you were out with Crazy Phil, no matter where you went the night was his right from go, and you just became one of his guests. He had a really overwhelming wiry, ADHD kind of energy– super impulsive, always moving, nonstop chatter. I think he’d be very difficult to sketch.

Around the time we met, Crazy Phil had recently been laid off from a job as a mechanical engineer and, instead of pursuing for another engineering gig, he decided he would try to make a living playing in underground and mostly illegal backgammon games. I had no idea such things existed, but Crazy Phil insisted they did. (I must confess there were a lot of things Crazy Phil said that I didn’t believe at first–including the fact that he held an engineering degree–but, miraculously, ever single implausible detail eventually proved completely true.) He spend all night at these clubs, which were filled mostly with older European and Asian men, all playing at pretty serious stakes, in relative backgammon terms. At least once, Crazy Phil flew to Istanbul because he’d been told there would be a very lucrative game there, hosted by some wealthy “pigeon.” (That’s what he’d call guys who loved to play the game and had lots of money, but were also pretty easy to clean out. Also, it should be noted that he referred to backgammon as “Gammon.”)

Eventually, many of those games dried up and Phil turned to poker. His life seemed crazy to me, because he would be up $20,000 one month and down $15,000 the next. He didn’t seem to care, though, and made a point of treating poker like a fulltime job. I remember him even telling me that he made sure to play 40 hours a week, just like a real job.

He was a lot of fun to bring to parties, and did this thing where he’d instantly treat any home as if it were his own. I never got the impression that he was consciously rude or had an offensive sense of entitlement; he just had no social safety valves between his thoughts and his actions. I’ve witnessed him take over someone’s bar at their own party and, at another apartment party, after noticing there was an active fireplace, Phil just started loading it up with logs and recruited all kinds of strangers at the party to help him kindle and maintain the fire. All this without even thinking to ask the host if this was cool. People usually let him run roughshod over their parties or restaurants or bars, though, because I think most of us lack the energy to resist or restrain personalities like Crazy Phil’s.

For a little while, Crazy Phil lived in a very small apartment in Chelsea with this Danish guy who spoke almost no English. He built an elaborate loft bed there, and painted all the walls either wine-red or black, like Dracula’s bedroom or something. When we told him his landlord probably wouldn’t be cool with having all the walls painted black, Crazy Phil just said, “Don’t worry. I already know we’re going to be here for a long time. The landlord just doesn’t know that yet.”

Crazy Phil once had a NYE party that he kept insisting was being professionally catered, and wouldn’t let us leave until the catering arrived. Finally, Tyler and I decided we had to split because the party was a little too weird—most of the guests were non-English-speaking Europeans and old men Phil had met through the ‘gammon scene, and Tyler and I were more interested in girls than hearing a 60 year-old guy strum an acoustic guitar in Crazy Phil’s tiny kitchen. Just as we were leaving, Crazy Phil’s buzzer rang. “That’s the catering!” he shouted, and insisted we stay just a few minutes more. He ran downstairs and returned a minute later holding four or five pizza boxes. To this day I have no idea if Crazy Phil actually considered these pizzas equivalent to a professionally catered affair, or if he was just screwing with us the whole time. With him, it could have very easily gone either way.

When Tyler and I lost touch a few years back I also lost touch with Crazy Phil, and didn’t hear about him again until this past weekend, over a Sunday afternoon drink with my optometrist. (I think my optometrist has always been pretty fascinated with Crazy Phil, which is not surprising to me at all. If you made a venn diagram of their respective personalities, the two circles would overlap so much they would almost appear as one.) Apparently, Phil moved to L.A. where he continued to play poker and, as the game became more of a national phenomenon, Crazy Phil emerged as one of poker’s more colorful celebrities. He’s accrued over $1.2 million in cash tournaments and has earned the nickname, “The Unabomber,” because he usually wears a hooded sweatshirt and sunglasses at the poker table and, when a hand gets really stressful, has been known to pull the drawstring of his hood so tight that his face more or less disappears inside it. (You can read all about this on his Wikipedia page.)

My optometrist also told me Crazy Phil has been dating Jennifer Tilly for a while, and these days has his own televison show on some HD cable network, where he and a friend go around betting on everything they see. Honestly, none of this surprises me at all–just as I wasn’t surprised when Crazy Phil dyed his hair an awful blonde on a whim, or when he had his New Year’s Eve party catered by Domino’s. It’s nice to know he’s found his way into the entertainment industry, where insanity is both tolerated and richly rewarded. (Ring a bell, Meryl Streep?)

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