Gambling for a Living — Part 2 (Not Just Another WSOP)

Here’s some advice:  Pay your taxes.  Preferably, every year.  On time.

Take it from the fool who’s danced upon the blade of the sharpest of spears and endured endless migraines instigated by the dreaded evil known as the Internal Revenue Service which lasted for years.  It’s all a nightmare, only you can’t wake up from the bad dream and when you do finally awaken, your awash in written threats and creeping deadlines.  You don’t want the IRS crawling up your back.  That’s an unromantic form of first base on the path towards getting fucked in the ass eventually.

Hey, I don’t blame the IRS for my seemingly endless, and ultimately very costly predicament.  I blame myself.  I accept full responsibility.  I freely admit to owing back taxes and very much wanting to pay my government, the devoted Socialist that I am.  We just couldn’t agree precisely on what I owed exactly, and I owed lots of back taxes on what I considered to be reasonable deductions taken years ago when money didn’t seem to be as big a deal that somehow snowballed into a giant shitload of interest and capital penalties and lawyers and paperwork.  Running a gypsy tab with the IRS is sorta’ like hailing that taxi from Manhattan over to New Jersey.  Only after you’ve crossed completely over the George Washington Bridge and approaching the exit ramp leading into Ft. Lee does the scruffy driver inform you abruptly the cab fare is going to be double because he’s driving way over to Jersey and has to get back into the city, all on your dime.  Oh, and you’re responsible for paying all the tolls, too.  That’s what it’s like to owe the IRS money.  Canines dig deep and they won’t let go.

One pitfall of self-employment over so many years — and I’ve been self-employed, a sorta’ free agent officially speaking off and on for precisely 17 out of the last 23 years —  is the maddening maze known as the federal tax code, which some self-claimed faux-billionaires somehow remarkably manage to exploit and not pay any income taxes at all, while working stiffs like the rest of us end up forking over parts of our anatomy to satisfy the 1040 bottom line.  Hell, the new President-Elect of the United States of America paid NO! FUCKING! TAXES! WHATSOEVER! WAKE! THE! FUCK! UP! AND! LET! THAT! SINK! IN! FOR! A! GOD! DAMNED! MINUTE! during the exact same years when the IRS was skip tracing and hunting me down like runaway fugitive, demanding their cut like a rag doll on shakedown.  Meanwhile, the incoming President-Elect brags that he paid NO! INCOME! TAXES! WHATSOEVER! WAKE! THE! FUCK! UP! AND! LET! THAT! SINK! IN! FOR! A! GOD! DAMNED! MINUTE! because — he’s smart.  I suppose that makes me and millions of others leashed to the IRS the dumbest motherfuckers on the planet.

After plowing through about $25,000 in liquid cash that I could barely afford, well couldn’t afford really given that I need fluff my bankroll like a peacock some more for the upcoming football season, and that’s just the legal fees and pencil-pushing accountants who didn’t know my name when I called them on the phone until papers had been shuffled off in the background and my file was located to they could refresh themselves that the client’s name is Nolan and I owed the IRS serious money, as in six figures, plus going to federal court and testifying once to fight the bloodsucking scoundrels who somehow were under the mistaken impression I was rich and hiding liquid assets under the mattress (check out my blog — all the money’s gone!  thank a few bad teaser wheels), I finally spotted my escape from the shackles of a perpetual audit in the form of one final massive lump sum payment to Dirty Uncle Sam, thus ending my decade-long ordeal of worry and misery and uncertainty and dusty unopened IRS envelopes piled high upon the desk laying aside losing sports wagering tickets.

The good news:  My IRS troubles were about to mercifully end.  The bad news:  Just about every dime I made in salary during the 2016 WSOP would go towards paying back taxes, plus the penalties and interest.  I’d be essentially working for nothing.

I reveal such an annoying tale of woe to you because my well-compensated temp position at the World Series of Poker, once again to be held at the glorious Rio All Suites Hotel and Casino in Las Vegas in late May through mid-July, would do absolutely nothing to pay the obligation of my monthly expenses.  Like masked moth men with butterfly nets, the government was about to seize it all, and I was all too happy to pay this genuine obligation just to make them go away and leave me the fuck alone.  Such are the twisted joys of working for what amounted to absolutely nothing for seven long weeks.  [Now, many of you know why I didn’t order that second bottle of wine at dinner each night.  One has to control the temptation, except for one night which I’ll write about shortly.]

Between the IRS lurking like vampires in the wings, the 15-hour days and nights spent on the floor at the WSOP, I’d still have to produce something from sports gambling in order to pay my bills.

Oh, and on top of all that, out of the blue, someone claimed I was a pervert.

Under these three ring circus-like conditions, I was to chart the St. Louis Cardinals starting rotation along with 31 other major league teams most days and check the wind direction blowing at the Oakland Coliseum and 16 other parks and stadiums, shop for the best line and total, get down on games, manage my four online betting accounts, and then find some time actually handicap a sport I thoroughly detested.

This was going to be a hot long-ass summer.

***

Edgar Allan Poe, the dead writer, is probably best known for his poem, “The Raven.”

“Quoth the Raven, nevermore.”  It goes something like that.  Hell if I remember exactly.  I think the bird was supposed to be spooky and even creep us out a little.

What most probably don’t know is — the author Poe was a sick gambler and a very bad one at that.  Accordingly to biographers, while he was a freshman at the University of Virginia the maven of melancholy racked up massive gambling debts, on what I don’t know.  I’d be curious to read Poe’s bad beat stories, of they were available, but then again of a black bird could scare the bejesus out of us, imagine how frightening a nightmare roulette session might read .  Once this apparent gambling addiction was discovered, his father became so enraged and got so pissed off at young Edgar that he instantly severed the patriarchal purse strings and refused to give his son any more money for school.  And so, the aspiring writer who was then no more than a lost teen got dealt the worst possible beat imaginable….

….he had to move to Baltimore.

Baltimore’s filled with scum, and the reason for this fact is, the great-great-great grandparents of the present-day scum living in Baltimore weren’t just scummy, but scummier even.  Look at Baltimore now.  What do you see?  Maybe more telling, what do you smell?  Cold acid rain, dank humidity, pockmarked litter-filled streets.  Now, imagine what it was like way back in 1840 before Capital Grille and air conditioning.  Who in the fuck would want to move there or live there?

Well, Edgar Allan Poe ended up in what amounted to the urban colonoscopy of Baltimore City, in part because an editor from a startup magazine nestled in one of those brick row houses of that dreadful place saw raw talent in the aspiring young author and agreed to publish his work for the princely sum of $50 a month, about what I’m pulling in now from my own writing endeavors, so I can empathize.  Hey, Poe — I got your back.  Yet, poor Poe ended up spending the rest of his miserable life in Baltimore, before he mercifully died at age 40.  His lifeless body was reportedly found laying face down in a gutter, which should be a dire red flag to all writers and wanna’ be writers.  If that’s the fate of one of our more talented and successful peers, what sad fate awaits the rest of us?  While living there, he reportedly drank a lot, engaged in the services of prostitutes (on $50 a month!), and did some other pretty lurid stuff which is pretty god damned amazing when you think about having all those vices and living on scraps.  One doesn’t know whether to detest or envy this condition, but at least Poe squeezed some mighty good times out of a meager salary.  However, when one thinks back to the punishment of living in Baltimore, such perversions must be forgiven.  After all, what else is there to do in Baltimore?

I pen this short interlude because there’s a lesson to be told here which should be plainly obvious to my writer brethren who also happen to be pro football fanatics, and students of history of the game.  Think of this:  Had Edgar Allan Poe not been a gambler, the NFL team now calling Baltimore home would instead be known something else, instead of the Ravens.

Baltimoreites and Baltimoreans, all — thank Edgar Allan Poe for being a shitty gambler.

***

Two essential qualities to gambling success are money and confidence — not in that order necessarily.  The requirement for the need for money is obvious.  Without cash, there’s nothing to gain, no risk, no upside.  Cash is oil to the flow of the gambling engine.

Accordingly, confidence is its drive shaft.  A gambler must have confidence, not to be confused with arrogance, in his or her decisions.  Poker players, who know this all too well, must trust their reads.  You inherently know when your opponent is bluffing, so you make the tough call.  It’s almost an instinct.  Advantage players must maintain faith in the card count, the proven long-term percentages which produce something known as “EV” for short, which translates into Expected Value.  In other words, played out a million times hypothetically, what’s the net expectation on such and such wager?  A sports bettor must trust in his information and the knowledge the he’s got the best of it when a ticket it written and bet is confirmed.  Then, once the game starts, a rookie punt returner fumbles the ball and demolishes all that pregame research.  One has to prepare for such crisis, and be willing to accept those events which we cannot foresee, nor control.

The first couple of months of baseball betting gave me enough confidence to continue the exercise.  By end of May, a full ten weeks into wagering daily full-time, I’d stepped up my bets to $200, then later $300 a game.  The training wheels were coming off.  By margins of previous results, betting $300 a game instead of just $100 a game should have netted three times the profit.  Since I made $1,500 profit in April, that meant by summer I should be pulling in $4,500 a month.  When I eventually get to betting $500 a game, that figure becomes $6,000 a month, which is $72,000 a year — in other words, a living.

Sounds too easy.

***

Tilt and temptation are the death ditches of gamblers.

Going “on tilt” means just what it sounds like.  It’s a old poker term, denigrating emotionally unstable players who can’t control themselves after suffering inevitable losses and bad streaks.  So beset they are with inner angst, they then fire outrageous amounts of money at the next betting opportunity chasing losses and hoping to get back to even, something I’ve done once or twice in my betting career.

Temptation can be just as dangerous, which means the inducement to fire far more on a game than one can afford, because the stars and planets and zodiac and talk show prognosticators all line up on the game way too perfectly.  It’s the “can’t lose” game.  The “lock.”

During the second month of betting Major League Baseball, I uncover a previously undiscovered angle that works and so I bet blindly it at every opportunity and this sunken treasure chest puts me about $3,000 to the good in May followed by $3,500 in the black in June.  Three consecutive winning months is certainly sweet, joyous even.  But it’s still a couple of grand short of my monthly nut, and more like $4,000 to $5,000 in added expenses short of what I need for the dinner-laden drink-infused dates on my social calendar for the WSOP which incorporates entertaining media dignitaries and old friends.  Last year, I plowed through $5,500 just on dinners at the WSOP (about 50 of them) with friends and colleagues.  Fortunately, Mark “Pegasus” Smith and Bob Slezak picked up four of the tabs, or I would have been on the hook for nearly another dime.

The bottom line was, even though I was making money, I wasn’t earning enough.  I was still falling way short of what was needed to exist, let alone prosper.  Under the conditions, while the gambling experiment was undoubtedly a success, my financial needs weren’t being met.  My bankroll might as well have been a popsicle, melting away slowing in the desert heat.

There was only one alternative, which was to start betting even higher.  And so, on some spot plays I made two considerably larger wagers, and won both.  Prompted by temptation and fueled by desperation, I wagered about $3,000 (twice) on two perfectly ideal betting situations that appear to already be in the bag.  In the first situation, some pitcher for the Toronto Blue Jays is on the mound against a worthless scrub for the other team, is laying about -190, and so I blast away hoping to cream off an easy $1,600 without even so much as breaking a sweat and acting like the game is already final.  While I’m obsessing over this on the night shift at the Rio, a couple of guys are playing for a coveted WSOP gold bracelet and I’m 30 feet away sweating the Blue Jays-Angles game on a laptop and hitting the refresh button on my smartphone every 30 seconds.  My bet wins.  A few days later, I find an similar spot where San Francisco Giants ace Madison Bumgarner (I remembered his name) is starting against some unknown mook who might as well have a broken arm wrapped in a cast.  San Francisco breezes effortlessly to an easy 4-0 victory on a masterful two-hitter, and I’m wondering why the fuck I’m wearing a suit and tie when it’s 109 degrees outside and working a job when my gravy train pitchers are making my financial life so damn easy and paying my bills, that is, except for the IRS which is still there with me like a garlic necklace.

Five or six days later, maybe it was a week, the Washington Nationals ace Strasburg takes the hill against some slug of a team, and while I usually hate betting heavy, heavy favorites, there’s some Twitter tweet that comes out that says the Brewers got caught in a rain delay at the Milwaukee airport the night before and sat on the tarmac for three hours before taking off to Washington National and finally arriving red-eyed at 3 am, only to be scheduled for an early day game the following afternoon.  Another $3,000 or so of my betting capital goes in the prohibitively-favored Nationals who then promptly go out and morph into the ’62 Mets.  My anchor Strasburg suffers arm trouble and gets yanked in the top of the first, and suddenly here I am holding the sitting duck of a 3K ticket riding on the arm of some Triple AAA bust out plucked from the bullpen in an unforeseen emergency.  The mediocre Brewers massacre the first-place Nationals and smoke my ticket like pickle ash and so the previous $2,500 roughly that was earned so effortlessly from the Jays and Giants games suddenly get seared like a fuck fillet.

Oh, and someone just won a gold bracelet, which requires me to suck it all up and put on a smiling face, as though I haven’t a care in the world.  This demands segregating thoughts, suppressing emotions, and taking decisive action.  In one room of the cerebral dollhouse of my mind is the lingering outrage of losing a sizable bet because Ryan Zimmerman grounded into a double play with the bases loaded in the bottom of the sixth.  Off in another corner of my mind — the written logs of poker narrative.  Time to go congratulate the winner on collecting $700,000 and his glorious first WSOP victory.

***

Naturally-gifted writers are often trapped within the purgatory of what they want to write and what they have to and are paid write, either to pay the monthly bills or not tick off the rest of the world and lose readers.  It’s a perpetual compromise that must be made and a perilous tightrope and no one I know walks it better than Brad Willis, known to many as the longtime blogger for PokerStars.com.

Brad and I go back more than a decade in what I think he’d even reluctantly agree is a sort of isolated chamber of a mutual admiration society.  Yet for all our common ground, both working for PokerStars, writing about the game, sharing frustrations, and working so many tournaments and covering so many stories over the years, it’s astounding that @bradwillis and I have never once sat down face-to-face at dinner.

That would change one rare off night when Brad and I found the time to dine together at the well-reviewed SLS steakhouse, Bazaar Meat by Jose Andres.  Brad generously agrees to front the entire expense, even without the knowledge I’d dropped $3,000 the night before on the Washington Nationals and was in serious danger of suffering my first losing month.  Despite this predicament, I couldn’t hang Brad out to dry for the full amount like that, since this dining experience was destined to be two things — epic and really fucking expensive.

And so, I cut a crafty and in my mind generous deal that I still think is really, really good for me and would still be expensive for Brad.  He’d pick up the dinner tab, and I’d pay for all the drinks.

I didn’t know it then, but another sorta’bad beat was about to come.

I don’t remember the amount of the dinner tab, exactly.  I think the set-course meal was somewhere in the neighborhood of $450, plus the tip, which Brad willingly paid without so much a grumble nor complaint.  I took care of the wine, a rare Gewurztraminer from the Alsace region of France that I’d never tried before which drank marvelously but was rudely contrarian to the customary dining standards of drinking red wine with red meat.  Brad and I didn’t give a fuck.  We ordered what we wanted and plowed through the evening like two sailors enjoying our last meal.

Following this two-hour dinner punctuated with laughs and memories and mutual frustrations and plenty of gossip about some of you now reading this, we agree to have “one more drink” at the SLS bar, which was out in the center of the casino.  Walking that direction, I think we both knew very well this wouldn’t be a “one drink” chat not a one-story encore, more like treking off to a Grateful Dead Concert as an afterthought.  Toss two writers into a blender, pack with ice, hit the whip button, pour into a shot glass, and leave a credit card open for the next round after round and the stories lead from one to another and by the time you’ve looked down at your wristwatch, as I did, it’s 2 am and the bar tab has somehow skyrocketed to more than $400.

Despite the expense, this ends up as my favorite night of the entire 2016 WSOP.  Worth every penny, my only regret is I didn’t take notes because there could have been a scandalous book written that night just from the scribbling.  And so, with that, Brad and I exited the SLS and both have to be back at work at noon the next day.  And I’ve got another fresh slate of baseball games to handicap in the morning.

Next:  Gambling for a Living — Part 3 (The Lunacy of Betting $7,000 on a Los Angeles Rams Pre-Season Game)