By Scott Tinley
March 09, 2007

Excerpted from Jackpot Nation Rambling and Gambling Across Our Landscape of Luck

Here's something I more or less promised in the beginning and it more or less happened this way and is more or less legal. But just in case my understanding of the law, as it applies to nimrods holding paper bags full of hundred dollar bills (even in the absurdly tolerant city of Las Vegas), is incomplete, I have withheld a few details and names. Anyway, the point of this story is not so much what happened, or even to whom, as what it's like to... hold a paper bag full of hundred dollar bills.

First of all, unless it's something you've been conditioned to do by daily routine (you're a drug dealer, a pimp, a college football booster), you would probably find it unnerving. I know I did. When I finally found myself alone in my car with the money, I immediately called my wife. "I'm sitting here with $100,000." I told her. "I may be in over my head." She would have agreed in any event but was especially concerned when I mentioned the amount. She had seen things go wrong with lots less.

The only thing I had going for me this time was that it wasn't my money. Not all of it, anyway. Not even most of it (but, for legal purposes, some). Still, I was in possession of a sum of cash that I couldn't replace if, for example, the draft of a passing trailer rig happened to suck it out of my car, spewing it movie-like along the Strip. I mentioned my concerns over the cell phone. "Roll up your windows," she said.

The reason I had this money -- the reason one of Las Vegas' most prominent gamblers had slid it across the table at an Outback Steakhouse -- was to prove the point that sports books were refusing any wagers that might be coming from sharps, thereby forcing action onto the Internet, where the betting could not be policed as well, and certainly not taxed. Inasmuch as the casinos' short-term fiscal cowardice might be harming the industry in the long run -- pushing traditional action offshore -- this might be important, or at least interesting enough to sidebar a bigger gambling story that Sports Illustrated was doing. So in a way, the two of us were performing a public service.

Just how had never occurred to me until our gambler, whom I had known from similar journalistic stunts, showed up at his favorite restaurant to lay it out for me. The idea, he explained, was to visit a couple of sports books, represent myself as a pro and keep betting college football until I was tossed. Being tossed was critical to the premise. It would prove the discrimination of dumb money over smart that was required of his thesis.

"So here's what we're going to do," he said, unfolding a piece of notebook paper with 11 bets scrawled on them. "We're going to bet these games until we can't bet them anymore." He promised me this wouldn't be that hard to do. Sports books managers were in such a state of panic when it came to line-movers like him and his runners that it might be possible to mistake me for somebody who knew what he was doing. He promised again: It wouldn't take long before our business would be declined. These guys were such chickens, he told me, I might be DQ'd the first time I bet the maximum.

"First time I bet?" I asked. "What maximum?" I must have misunderstood. I was used to tagging along with people, listening in, watching. That's how I roll. "Well, I can't bet," he said. "I thought that much was obvious. Anyway, here's the lines -- try not to get nicked on the price -- here's where to bet and here's the money." And, like I said, he slid a small handled-bag across the table. It was a little bigger than a lunch sack, but not by much. I looked inside. "That must be..."

"It's $100,000," he said. "You want to be careful in the parking lot with that."

I gave it a better look inside my car. It was all bundled, some in $10,000 packs, some in $5,000. Not many people see so much cash in a paper bag that are not, by the very nature of the transaction, automatic flight risks. That wasn't going to be a concern here. The real problem, the way I saw it, might be bookkeeping. That is, once I took my wife's advice and rolled the windows closed. His instructions as to size and placement of bets were specific but I couldn't imagine myself presenting a checklist at the sports book, especially as I was representing myself as an adversary, someone who deserved to be chucked. There was no way I was going to be able to account for this much action without an accountant at my side.

But this was a Saturday, a rivalry week in college football. For the moment I could enjoy my second-hand wealth, which meant returning to my room at the MGM Grand and mounding the stacks of cash in various pyramids. Oddly I quickly grew bored, piled the dough back into the bag and went down to the casino, the handles of the bag looped over my arm so I couldn't easily forget it under a table. Using my own money (I'm not an idiot), I enjoyed one of those nights that large corporations are able to suffer (short-term) in the anticipation of comeuppances down the line, which you have already learned. I won $11,000 at a $100 blackjack table and salted the bag with my cash (satisfying a legal loophole), entering the supplement into the books. I was pretty glad to be able to do this, piggybacking a gazillionaire's picks. I'd get a story, and a pretty good payout, too.

Well, it went down pretty much as he said, more or less. At Caesars Palace, where he had said it had gotten especially paranoid, I waited for his call. After comparing timepieces, military style, he instructed me to bet the maximum on Kentucky, plus 19 at exactly 8 a.m. Understanding the maximum to be $2,000 (who'd ever want to bet more?), I walked up to the counter and, looking side to side as if I couldn't have been more bored with the proposition, made just such a bet.

My cell vibrated to life within seconds. My gambler was furious. "You have to bet the maximum!" He was shouting. "They'll never take you serious. Get back there, bet $7,000, quick, same game." The most frightening thing wasn't that I was bobbling this whole scheme -- I expected that would come to pass -- but that he had known what and when I had bet. Was he wired into the system? Was I being watched? What else was going on behind the scenes? I bet again, looking even more bored, then walked away, per instructions, to consult my sheet and grab another stack from my bag.

And so it went. The crowd around me was fairly delirious, with a lot of Ohio State fans facing off a Michigan contingent, dozens of huge screens around us, the broadband equivalent of Dante's Inferno. I permitted myself a smirk of self-satisfaction, imagining myself above this partisan fray. Were they carrying gift-bags with $100,000? I thought not. I was doing serious stuff here, tilting odds, flinging huge sums of cash at fate, daring it to deny my rightful and rich destiny, plunging myself into the maws of probability, joining the world of risk-takers, massaging the future to my advantage.

I was going a little nuts, basically. On my fourth, increasingly torpid trip to the counter (I waited for a call each time, becoming ever more precise in my timing and betting, and did not get yelled at again) it finally happened. A manager from behind the counter, who'd been watching this charade, appeared and, while not actually kicking me off the premises, said my day was done here. He'd pegged me for a wiseguy, the type of bettor who could bring this whole operation down, probably cost him his job with my obvious inside information. My action was no longer welcome.

I couldn't have been prouder. It was no longer about proving out the story; I had been recognized as somebody who worked beyond that science of incomplete knowledge, somebody who had mastered this little part of the universe, somebody who was right far more often than not. Of course I was only somebody with a piece of notebook paper and somebody else's money but, still...

There was nothing left to do but return to my room and watch a little football, then make my rounds, divide the winnings, and settle up. As it happened -- and this should be a lesson to all you would-be wiseguys out there -- there wasn't that much making of rounds to do, very little dividing of winnings and not so much settling up. To my horror, 8 of "our" 11 picks were losers. This should also be a lesson to sports book managers: Take as much of everybody's money, smart or dumb, as you can.

So all I had to do was retrieve the paltry winnings, stuff that money back into the sack and rendezvous with my gambler. Back at Caesars, I thrust all the betting slips forward, letting them sort the winners from losers, took the miserable remainings and disappeared, no longer so sure of myself. That night, as per instructions, I met my gambler at the parking lot of an In-and-Out burger place way off the strip. He pulled up in a sleek Mercedes coup. He was all decked out in formal wear, on his way to a charity function. He laughed at our luck. "Pretty pathetic," he said. And off he went.

That wasn't the last I heard from him, though. As I expected, I screwed up cashing in the betting slips, one of the games (a winner!) not quite final when I did my collecting. That's a bad phone call when a gambling titan calls you at 6 a.m. on Sunday and advises you he's $9,000 short and do you know anything about that. Luckily -- the only luck we had among us that Saturday -- I had saved all the slips for scrapbook purposes. Sure enough, among them was an uncashed winner.

I returned to Caesars, a little of my smugness called up for the occasion, got my dough and drove off to a different In-and-Out parking lot to settle up, for good, I hoped. I was somewhat humbled by the experience, as much for my incompetence as a bet-runner as our luck, which after all included the turnaround of most of my $11,000. My gambler, who'd lost quite a bit more, didn't seem to mind, laughing the whole experiment off. At least we proved our point, whatever that was.

Before I left, though, to return to my square world where paper sacks held baloney sandwiches, I did a quick surveillance of the parking lot, wondering who else was there settling up, their bags fuller or maybe even emptier than mine had been. There were a lot of nice sports coupes parked at a fast-food joint for a Sunday morning. I had become a bit addled from the whole experience, of course, my imagination inflamed by the temporary stewardship of so much cash. Still, it occurred to me, with a little shock: Was I likely the only guy in town carrying $100,000 to and from work? Exactly how far in over my head had I been? The sports coupes peeled in and out on a Sunday morning in Las Vegas, too early for burgers, NFL kickoffs coming up.

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