Gambling for a Living — Part 1 (How I Got to Now)
Since March 2016, most of my attention has focused on sports gambling, more precisely beating the books. This is a detailed retrospective of that emotional and financial (mis)adventure over the past ten months.
The decision to gamble for a living wasn’t borne as much out of naivete that I could conquer the odds and beat the Las Vegas sports books at their own game, but rather drifted from a sobering and starkly frightening realization that, for me, at this stage of life, few other alternatives existed. In the period once crooned by Sinatra as “the September of my years,” I had few cards left to play.
For many years, I’d worked the “house” side of gambling and was quietly content to remain as a well-paid shill. In plainer words, I crossed the River Rubicon of Risk over to fishing for the sure thing in a barrel a very long time ago. Playing poker and sports betting became merely peripheral part-time pursuits, jolly distractions even, secondary to the time-clock punching guarantee of a steady paycheck signed by whichever master I was serving — be it now defunct Binion’s Horseshoe, the World Series of Poker, PokerStars, Poker Night in America, or any of several other gambling giants and entities which for whatever reason thought my rare talents were worthy of generously steady compensation. Winning and losing a football bet over the weekend might have indeed determined if I’d be tilting Gevrey Chambertin or Gnarly Head toward my lips the following week, but I’d still drink my wine, bad beats be damned. With rare exceptions, like when I blasted off the princely sum of $39,000 on the disastrous 2008 Super Bowl game, gambling outcomes and even the grind of being in action almost every single day rarely impacted my financial bottom line or altered my lifestyle. The mortgage got paid — sometimes even on time. Gambling outcomes rarely affected my psyche, except when I lost.
All that was about to change — in a big way.
Hunter S. Thompson, the dead writer, was a sports fanatic and passionate gambler. He once wrote he hated the Dallas Cowboys so much that he unfailingly bet against them every single week for a whole couple of seasons. That wasn’t a very smart thing to do in the 1970’s, which were glory years for Tom Landry and Roger Staubach. So, famished and eventually flummoxed, Hunter flip-flopped over the dark side of the silver star, started betting with his head over his heart, and ended up loving the devil Cowboys — but only when they covered.
I’m not sure why, but most writers seem to think we have all the answers to everything and can figure out anything, from solving the world’s problems, to how to profitably handicap a professional football game. Between snorting fat lines of coke, guzzling fifths of Chivas Regal, and popping enough quaaludes to fell an wild elephant, beastly Hunter even quasi-authored a rather shitty book on the subject if I do say so myself, a rambling collection of sometimes incomprehensible essays, really, a maniacal bitch fest about the crookedness of the NFL, the hypocritical league, the ghastly owners, and effervescent frustration with his inability to pick steady football winners, despite being smarter and more ballsy than just about anyone else on the planet.
I feel Hunter’s pain. Pass the Chivas.
I can’t explain why I picked baseball, really. When it comes to gambling on ball games, “biesball has not been bery, bery good to me.” Frankly, I don’t even like the fucking game. I don’t watch it. I won’t watch it. I refuse to watch it. I don’t enjoy it, even on the startling occasion when I manage to pick a winner. I spent Game 7, yes that game 7 with the Cubs beating some underdog team from the American League, of last years riveting World Series of Baseball championship dining in my favorite restaurant, where I received impeccable service since the joint was empty. I hold no rooting interests, other than cheering for whichever team happens to be playing versus the evil Yankees, Mets, Red Sox, or Dodgers. When the Yankees play the Red Sox I root for rain, or a stadium collapse. That’s the extent of my interest in major league baseball. Give me a rain out in Boston, a stadium collapse in New York, and a winning day betting baseball elsewhere, and I’m bouncing off the wall in ecstasy.
But for the next four months, at least, that late spring to midsummer lull when all the sports that really matter are on break, baseball was going to be my total focus and (help to) pay my bills. And falling short of that lofty ambition, if I lost money betting on baseball, why then I’d hate it even more so than before. So, this was a sort of sadistic win-win for me. Baseball was like the homely girl everyone avoided in high school. I wasn’t just asking her out to the prom. I was proposing to go steady. But I wanted no piece of her.
Two prior periods of my long life shoved me into the wolf’s den of full-time gambling and both were spin-offs of unemployment and laziness, in roughly equal parts, with a slight lean in percentage toward being lazy.
Thirty years ago, fresh out of university with a worthless college degree that fortunately didn’t leave me bankrupt because I attended a state school (thanks, Socialism), playing underground poker six days and nights a week became not so much a passion as a reaction to the blunt realities of the times and the accidental trips and falls of aimlessness. It wasn’t that I was a good poker player. No, not at all. But unlike those around me, burned out lives stoked with dangling cigarettes from their mouths,who had never even heard the name David Sklansky nor had read Mike Caro’s groundbreaking Hold’em Report which first came out around that time, I read their ideas and studied and digested every word. Lucky for me, my opponents in those bottom-feeder low-stakes games were so horrifically awful that just about anyone who was patient and knew hand rankings could grind out just enough to stay ahead of the bill collectors, even without an answering machine screening the calls. Despite steady losses, still they could always afford cigarettes and another buy in. I never did figure out where they got their money.
I never beat those games big. But, I beat them for enough. Just enough to get by. And that’s really saying something.
Still, none of this skip down memory lane mattered now, not now in March 2016 with a much bigger monthly financial nut to crack and a different kind of poker game that might as well be speed chess to checkers in a nursing home. Beating poker a couple years back in the ancient ’80’s and trying to compete today were disparate pursuits. One simply had nothing to do with the other. Even a few years later, starting in 1993, when poker was legalized at casinos in New Jersey, I played Atlantic City’s juice fest on weekends for nearly a decade during the fasten-your-seat belt 90’s, a winning pedigree back then is meaningless now. The games and its players are just way too different, certainly much better, today than back then. Besides, who wants to spend 60 hours a week trapped inside a poker room hunched over a table in backbreaking convention-style metal chairs? Even if I could beat the game, and that’s a big if, I don’t even think I’d want to try. Life’s too short to return to the assembly line.
That pretty much left me with just one option to make a living — sports betting. Yes, there was a time, 17 years ago, when I lost my job and then spent two whole years without a steady paycheck. That’s when I first moved out to Las Vegas to bet sports. And the rest, as they say, is history. Things didn’t exactly go according to plan, of course, but I have no complaints.
None of this matters now. I bring up past gambling experience not to establish street cred, which I may or may not have, but as veritable evidence that I was acutely aware of the weight of my challenge ahead. Winning consistently at something that was difficult to beat two decades ago doesn’t translate into the modern era. Moreover, now that I need to make even more money than way back then, the task was even more perilous. It’s one thing to win at gambling when you’re single living in a $600-a-month apartment back in the 1980’s and walking around with more money in your pocket than your car’s worth. It’s quite different with a family and a mortgage and a health insurance premium due each month, and nothing to fall back on when the inevitable cold streak rears its ugly head and breaths dragon fire.
The image of the professional gambler is just about total bullshit.
Gambling for a living isn’t glamorous. It’s not even fun, not most of the time. Hell, it’s hardly the least bit interesting after you’ve done it for a while. The routine becomes a grind. A bore. Wins, when they happen, bring no genuine joy because every gambler, even very successful gamblers who do this over many years, know the gremlin of a cold streak is just around the next corner, ready to pounce and mind fuck your head and strip you of your bankroll like a thief lurking in a back alley.
But the biggest misnomer of all about successful gambling are the betting amounts attached to what defines being a winner. Non-gamblers often mistakenly believe gambling requires big bets and vast sums of money. To the contrary, the majority of people I know who gamble for a living, especially over very long periods of time, earn what would be considered very average incomes. Earning $60,000 a year at the poker table or even half that betting on sports is nothing to sneeze out. Even modest returns place the rare winner into an elite top few percent. While the tales of nosebleed poker games happening in big casinos might capture the public’s attention, the far more steady performers are those remarkably talented and disciplined individuals who quietly grind out a living day in and day out for years, and decades. That’s professional gambling. That’s the majority of successful gamblers.
Golfer great Lee Trevino said it best. About gambling, he said, “pressure isn’t measured in dollar amounts, it’s betting $10 on a match when you only have $5 in your pocket — now, that’s pressure.” Accordingly, I never quite got the fascination with high-stakes poker games or tournaments filled with billionaire businessmen or sponsored poker pros. So, one mega-rich guy beats another mega-rich out of a million dollar pot? Who cares? I want to watch the game where the loser can’t afford to eat the next week and has to go live under a bridge. Now, that’s exciting.
While I doubt I’ll end up under any expressway if I lose, indeed, if I do lose — the bills don’t get paid. Bill collectors call. When you lose, especially when you lose a lot, the world pretty much sucks. Everything about the world just flat out stinks. While it might have been more fun, relaxing even, firing $39,000 on a Super Bowl game when I had $50,000 in stray chips parked inside a drawer somewhere in the house and bet $1,000 on halftimes for shits and giggles, the thought of betting ball games with my case money is far more riveting, and excruciating.
Early season Major League Baseball starts out well.
I make absolutely no claims to having any expertise on this subject. But I do understand contrarianism and the very crucial concept of mean regression. I’ll avoid a lengthy tutorial on early season baseball betting because you just want to enjoy my aches and pains, although I’ve penned plenty of research in the topic. However, let’s just say there’s some value in fading last year’s win-loss results, betting against the so-called “hot” pitchers, and wagering against popular public teams expected to perform well in the regular season. I’ll leave it at that, unless someone wants to stake me in the upcoming baseball season. They, you get all my secrets for free. E-mail me offline for details.
Betting no more than $100 a game, that’s right, a hundred measly bucks, but often betting 8-10 games a day, I manage to run my account up $1,500 to the good during the first month of my new full-time career as a professional sports bettor. No worries that I’ve fallen about $4,000 short of what I need to cut it each month, which is somewhere in the neighborhood of 5 to 6 K. But, I can honestly report that sports gambling moved me closer to my goal than I would have been otherwise had I just sat around and typed blog posts and bitched about Donald Trump’s alarming rise on the polls. Besides, beating sports comes as a nice diversion from the looming reality that the end of Western Civilization may be near.
It remains to be seen if this gambling thing will continue to work out. But my modest ambition was a success, so far. That said, I’ll have to step up the size of my bets at some point if I really intend to make a living at this. in the meantime, just avoid the gremlin.
Coming Next: Gambling for a Living — Part 2 (Not Just Another WSOP)