Money for Nothing: One Man's Journey Through the Dark Side of Lottery Millions

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Chapter One

Gonzo Goes Fishing

August 1997: Southeast Florida

I am watching Tommy roll another joint, one-handed, while driving his new boat straight out of the inlet into the Atlantic Ocean. I'm laughing so hard it's making me even more nervous, happy, sad, stunned. I just made a serious commission off this guy and he's taking me out fishing, too. Forty minutes ago, we were at his bank notarizing the signature pages of his contract. Now, we're off the clock.

Thank God I left the contracts in the car. There's sea spray everywhere. They would be soaked, and I'd be beside myself—just beside myself.

Tommy's someone you like right away. Three years ago, he won a handful of millions in the Florida Lottery. Tommy swears he was happier before he won. I know he's telling the truth. That's one of the reasons he trusts me—because I know it's true. Two days ago, he called our office looking for money after seeing our commercial on The Jerry Springer Show. Within seconds I knew. This could be big.

Tommy's wearing nothing but a pair of cut-off jean shorts. He is tan, his skin leathered from a life on the water. This is not his first time in the sun. I, on the other hand, am fat and pale. A chain smoker, Tommy sounds like a young Wilford Brimley. I like him a lot. I just do. He's funny—and we both love to fish. But I can tell that he can be a mean son of a bitch. If he only knew. . .

The sun feels like it's thirty feet over my head. I'm burning everywhere. This is not the kind of boat where you golathering yourself up with SPF 45. I imagine Tommy would not be inclined to rub the lotion into my tough-to-reach areas. I will burn like a man. I hate being manly. I want a Diet Coke. All we have is Budweiser.

I'm sweating. Tommy yells something to me. I hear nothing over the screams of the two huge engines mounted on the back. One engine would definitely be enough for this boat, but we have two . . . lucky us. Typical lottery winner, the nouveau riche of the nouveau riche. They buy two of everything when one will do.

Tommy looks back and hands me the lit joint. He says something. I can't hear him over the goddamn engines. I'm pretty sure he said something about the money. I laugh as if to infer that I both heard him and agree with whatever he just said. At this point, it's best to just agree.

I'm in no mood to smoke, but I'm not about to refuse his offer. I take a long, deliberate drag on the joint. I close the back of my mouth so I look like I'm toking away. The smoke gets sucked into the engine exhaust before I inhale it. Tommy doesn't notice. Lesson 101 in sales: If a customer offers you something to drink or eat, you accept. It's just good manners and it puts the other person at ease. It's good for business—any business.

It's 3:45 in the afternoon and I'm faking a joint with a client. Why? Because he wants to, and I'm here to make him comfortable. Not a typical day at Smith Barney or Goldman Sachs. It is, to be sure, closer to car sales—very expensive cars.

Tommy is going this fast to (a) test me, (b) scare me, or (c) impress me. He has actually done (d) make me want my nana. I'm too numb and hot and happy about the deal to be truly scared. But deep down, I know I'm in a tight spot. At the very least . . . the very least, I'm not exactly acting like the son my father raised. Pretending to smoke a joint with a lottery winner just after signing a deal with him is not quite the career my dad had in mind for me.

I think Tommy just said something about his lawyer reading a copy of the docs. Goddamn engine noise. It doesn't matter now. The deal's signed. I nod and smile. All I can think about is holding onto any part of the boat that is bolted down—and not dying. The skin cancer I'm bound to get is a longer-term issue. Falling out of the boat, three miles out to sea with a stoned multimillionaire, is a more pressing concern.

Tommy has no idea how we make our money. They never do. He thinks we're fishing buddies. I wish we were. I will be sorry to disappoint him—that part always stings. But, in the end, more times than not, these deals are one-night stands. He offered to put me up at his house, for Christ's sake. He didn't even want me to check into a hotel. He can roll a goddamn joint with one hand. I like Tommy. I could use a friend like him in my real life.

In two weeks, he will threaten to kill me. He will mean it. And I will deserve it.

What kind of job makes all this possible, necessary even? To see the lump-sum business for what it really is, to understand that it has next to nothing to do with finance and numbers, you have to appreciate the kind of folks that win the lottery and the kind of guys who wait in the weeds for them to surface.

Tommy's first call to The Firm surfaced late in the evening, when decent folks were already home. I was with Ben at the bar, for a change. We were both still in our work clothes, as we'd come straight from the office—four hours ago. We were still working, in a sense, as our cell phones kept ringing with sales reps from all over the country calling in to give us (Ben, really) updates on the status of their deals. So far that night, over a handful of cocktails, we'd both made money as two deals had been signed, all while we guarded our favorite bar stools.