Depraved Derby, Mayweather-Mosley, and Betting on Wookies

By Pauly
Los Angeles, CA

Forty years ago, a piece of literature was birthed, which would change my life forever.

The Kentucky Derby is Decadent and Depraved is my favorite article ever written by Hunter S. Thompson (my second favorite is A Dog Took My Place, a piece in Rolling Stone about the Roxanne Pulitzer trial in the 1980s).

Scanlan's Monthly magazine sent Thompson back to his home state of Kentucky to cover the "fastest two minutes" in sports. I'm sure Hunter convinced the editors that only a true Kentuckian could write an insider piece. The 1970 Derby assignment was the first time that he was teamed up with illustrator Ralph Steadmen. As the story goes, the proper Englishman was given mescaline (or mushrooms depending on who you talk too) when he initially met Hunter. The psychedelics rocketed Steadman's mind into the cosmos. His artwork has never been the same since.


Ralph Steadman's vision of the 1970 Kentucky Derby
Tom Wolfe, a true Southern gentleman and fellow scribe, adored Hunter's Derby piece because as he described, Hunter gathered astute observations on all of the sordid characters: drunk Southerners, weird socialites, and bookies. Hunter effectively covered the Kentucky Derby without even writing about the race.

"And unlike most of the others in the press box. We didn't give a hoot in hell what was happening on the track. We had come there to watch the real beasts perform," Thompson wrote.

That style and attitude influenced me during the 2008 WSOP (and you can argue as far back as 2005). If you were an avid reader of Tao of Poker, you might recall that I got through almost four weeks of the 2008 WSOP without writing about a single hand or posting a chip count. I dunno how the hell I was able to get away with it... but I did. Anyway, in true form, I hope to return to a similar philosophy this year.

Certain spectacles exist that everyone must see and experience before they die. If you're any sort of degenerate gambler, then Churchill Downs in your own personal Mecca. You must make that pilgrimage in your lifetime. I went to the Kentucky Derby once. Once. I was in college, a snot-nosed frat boy in my late teens, and we road tripped from Atlanta. We hung out in the infield with tens of thousands of other drunk yokels. My poison of choice in the early 1990s was Jim Beam and diet coke, but we also smoked a dozen joints of Mexican ditch weed before the fifth race, which is why I don't recall too much from that afternoon. I think Sea Hero won that year, but I didn't cash any winning tickets.

I bet on the Kentucky Derby every other year, depending on where I am at the time. This year, I got a bunk tip from a CIA operative. I'm starting to think it was disinformation, but who knows for sure. Maybe they were really trying to fix the race, but some of the jockeys didn't cooperate?

Have you ever gotten drunk with a jockey and got him to tell you bad beat stories? Fascinating material. Jockeys appear tiny in stature, but they are some of the most courageous athletes out there, and put poker players to shame in terms of enduring their share of unfortunate incidents. I demand $1 if any poker player tells me a bad beat, but will willingly fork over $20 to hear a jockey tell me one of his bad beat stories.

* * * * *
It takes money to make money. Didn't Warren Buffet say that? Or was it Billy Shakespeare?

I looked at the odds in the Floyd Mayweather vs. Sugar Shane Mosley fight. Mayweather was the overwhelming favorite according to the shylocks in Vegas and the offshore bookies. If you wanted to bet the longshot, Mosley was +280, which made sense, he was roughly a 3-1 dog. However, if you wanted to bet Mayweather, the lines were around -365.

Fuck me, who wants to risk $365 to only win $100? But what if I told you that it was easy money and it would be foolish to not bet it? The accumulation of wealth is not always built on logic, but the occasional gamble, even though the odds are shitty.

My old mentor on Wall Street once told me, "If you feel as though you have the winning edge, you still go for it. Balls to the fucking wall."

That's why I bet my entire online sportsbetting bankroll on Floyd Mayweather. Balls to the wall. Fuck the Derby, Mayweather was going to be my horse.

Four years ago, I never could imagine betting against Sugar Shane Mosley in a fight, yet sometimes attitudes change, especially when there's a financial incentive on the line. The last time I actually won money betting against Mosley were both of his fights against Winky Wright in 2004.

I rarely bet boxing and when I do, I'm usually pissing my money away on long shots. I also know very little about boxing. My brother and a few other friends are avid fans and know a fair amount to make educated opinions about the outcome of certain fights, but word on the street was that Mayweather was gonna whoop Mosley en route to an eventual (hopeful) bout with Pacman.

But shit, Mosley is older than me. It would have been foolish to bet on a washed up palooka. Smart money was on Mayweather, but the bookies didn't want to exactly give it away. Hence the -365 on the board. That did not deter me. Easy money was my motivation.

I didn't watch the fight because I'm in the middle of the final read through of Lost Vegas and got stuck in an editorial meeting all evening. We had taken a break during the afternoon so I could watch the Derby, but the fight was off the radar. During one of our breaks in between editing chapters, I checked out one of the live blogs covering the fight. It was only the third round at that point and Mosley had gotten off to a tremendous start and appeared to be ahead on most scorecards. However, he shot his load in the second round and Mayweather took control of the remainder of the fight en route to an unanimous decision.

Like I said, easy money. If only every sports bet were that simple.

* * * * *
I don't watch American Idol, and you figure that I would since I have a bet on Crystal Bowersox to win it all. I watched a few episodes with my girlfriend, who is an avid fan and even writes about the topic from time to time. She kept gushing about this "wookie girl" -- a white girl with dreadlocks who played acoustic guitar and had the voice of a black soul singer.

I saw Bowersox during Rolling Stones week and she killed You Can't Always Get What You Want. Change100 insisted that Bowersox was the best of the bunch (at the time) and wanted me to place a bet on wookie girl for her. After seeing Bowersox's sizzling performance, I felt confident in Change100's call. I don't watch American Idol, but I've been over a thousand concerts (which is why my hearing is slipping) and have probably seen almost a thousand different live acts. I might not be up to par with Idol's judges, but I definitely know when something is musically appealing. Bowersox looked like a lock, a sure thing, and we all know how I feel about easy money.

At the time with a dozen or so to go, Bowersox was listed at an almost 2-1 favorite. Currently, she's listed at 1-2 with less than five contestants to go. Yes, the bookies think it's her contest to lose. The only thing I have against me is the potential that the producers rig the outcome, which is to say, that aspect is out of my hands.

Alas, I'm pulling for Bowersox to win America's greatest karaoke contest. If she can ship American Idol, then I win a couple of hundred bucks, which will cover my ganja needs on summer Phish tour. Who knows, maybe I'll run into her in the lot somewhere on tour. If I do, I'll be sure to smoke her up.