Why a Big Shot Like Me Plays the Lottery

When the Mega Millions lottery got over $225 million recently, I went into the deli and bought a New York

When the Mega Millions lottery got over $225 million recently, I went into the deli and bought a New York Post. See, I don’t like the idea of just buying a lottery ticket—feels sketchy, low rent. So as I was paying for the paper, I said, “Oh, and give me a Mega Millions, too, thanks.”

I bet porn fiends, pre-Internet, used to do that: “Oh, I’m just walking down the street, down Eighth Avenue in the 40s, minding my own business, running errands, and hey, what’s this new establishment? Peep World. Maybe I’ll take a quick peep inside, see what the fuss is all about. Yes, I would like some tokens, Pakistani guy behind the counter, much obliged. Ahh, I see, the booths are in the back, near the man pushing the mop. Well, I wasn’t planning on coming in here today, but …”

My first time was in 2004. I was pacing outside a newsstand on 72nd Street, pretending to check my cell phone messages. As soon as the place cleared out, I darted in, grabbed a Vanity Fair and asked for a Mega Millions. Before I could have my $103 million fantasy, four creamy private-school girls (I’d guess Dalton or Spence) got in line behind me. The Indian guy was taking his sweet time with the ticket and said, “Just one Mega, you sure?”

I heard one of the Serenas say, “Did you see what that guy was getting? A Vanity Fair and a lottery ticket!”

Wonder what she’s up to these days. Out of college for a year. Parents haven’t cut her off but she’s living with three other girls on Park Avenue South, can’t find a job, slutting around, pigging out, 33 pounds overweight.

There was a time when I, too, felt disgust for lottery ticket buyers: That was something one’s servants did. In fact I’d rather be seen by a rich WASP lady as I was leaving a porn emporium than when buying a lottery ticket. They’d get on the horn and be like, “Guess who I ran into the other day? Do you remember that silly, no-good pissant George Gurley? I saw him and he was … sorry, can’t contain myself … he was … buying a lottery ticket! Oh-ho-ho!”

These days I buy once a week, preferably when the payout is north of $50 million. I’d feel like a real sucker if I won when it was only $15 million, because after taxes you only get a third, and what am I gonna do with $4.5 million? Buy a sweet townhouse in the West Village? Great, now I’m broke again, thanks a lot.

If I won big, like $270 million, would I really be happy? Definitely, for at least six months. Beachfront property in Bermuda would be nice. Still afraid of Jamaica. Those rastas seem real friendly, then they’re doing voodoo and nailing you to a tree like a rooster.

The other night I went to a party at Allison Sarofim’s Greenwich Village townhouse. In a tent out back was a Henry Moore sculpture and waiters holding trays of burgers and Champagne. I went to school with Ms. Sarofim in Houston. I had a swimming pool back then, and access to a Jaguar. Pavarotti came to dinner. I didn’t think anything of it. Was into basketball, this girl Hope, weed, beer bongs, go-carts, the Omen trilogy. Twenty-five years ago. Couldn’t care less about money.

It was like I was born on third base, like George W. Bush, but I ran in the wrong direction.

At the party, social butterfly Euan Rellie, wearing a dark blue fitted silk jacket, told me he buys lottery tickets when it gets over $200 million or he’s feeling depressed. A while back I had to read that he was looking at $5 million townhouses downtown and it really stuck in my craw. Mr. Rellie told me he’s not happy about the tax situation.

“I’m all in favor of a progressive tax, but it’s gotten too progressive now,” he said. “I have to pay a lot of money in taxes, because I’m an investment banker and the only way I can get back is by winning the lottery.”

If he won, he said, he’d take his wife, Lucy Sykes, to Harry Winston to upgrade her engagement ring. “Bryan Adams, the pop star, said to me, ‘Your wife has a canardly ring,’” he said. “And I said, ‘What’s a canardly ring?’ He said, ‘Canardly see it, it’s so small.’ And my wife has always assumed that I’ll get rich sooner or later, and she’d like an upgrade. At this point, I think she’d settle for a $600,000 ring.”

What else would he buy with his winnings?

“I’d throw a party that people come to who don’t know me and have never heard of me, but they still hear it’s going to be such a lavish party, that they’ll come anyway.”

What about giving a few thousand to homeless beggars?

“No, I never give money to people on the street asking for money. … Oh, what the fuck is that? Oh, it’s the neighbors.” Someone next door had crept up to the wall and was shooting water at everyone from a garden hose.

A few nights later at the Four Seasons, the restaurant’s co-owner Julian Niccolini told me he buys a lottery ticket every day. “I would go back to Italy, sit in the sun, have some good, great sex,” he said. “I would do charity: Citymeals-on-Wheels. Then more Italy vacation and more and more sex. I give all the money to charity and then have more sex.”

At the Metropolitan Club, I ran into Jan Amory, at a book party for An American Experience: Adeline Moses Loeb and Her Early American Jewish Ancestors. Ms. Amory, who was wearing sexy pajamas, was once very wealthy and dated big shots like Warren Beatty and Henry Kissinger. She lives in Newport and buys a Quick Pick every other day. What does she fantasize about?

“I just remember what I did, so it’s kind of, Can I do it again?” she said. “I’d take 20 of my best friends to the Hôtel du Cap in Antibes for a week and charter a yacht. It would be all my friends who’ve been good to me since I lost my money, not the other ones.”

Nearby, Wendy Vanderbilt told me that her maid turned her on to the lottery. “I believe in magic!” she said. “Imagine, it turns out to be a Vanderbilt who won $20 million! I’d put it in the bank and think carefully about it, because I think you’d go crazy when you won it.”

Later in the week, I went to a party for Michael Gross’ book, Rogues’ Gallery, at Georgette Mosbacher’s Fifth Avenue apartment. On the way out, I asked Thomas Hoving, the former director of the Metropolitan Museum of Art, if he’d ever bought a lottery ticket.

“Never. Fuck it,” he said.

  Why a Big Shot Like Me Plays the Lottery