A $20,000 bottle of wine? Welcome to Wall Street

The sommelier opened and presented the bottle. He poured a few drops in front of Tom, the broker picking up the check. Tom sipped it and then closed his eyes. We all watched in anticipation. Tom opened his eyes ad nodded yes. It was a good bottle.

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As I took my first sip, the guy to my left leaned in really close.

"You know," he said. "Only 0.1 percent of the population will ever taste a wine this good."

"Really," I said taking my second sip.

"That's Bordeaux — a $10,000 bottle."

"What???"

I whipped around to look at Tom and, in the process, my elbow and forearm took out my glass, his glass and the entire bottle. The $10,000 was soaked up by the tablecloth in a matter of seconds.

"I'm so sorry," I said. "I-ah, um. I'm sorry."

"It's okay," Tom gritted through his teeth. "Seriously, don't worry about it."


Two hours and $32,000 later, the check came. As I got my coat from the coat check I saw the sommelier look at me. No words, no smile, no expression — just looking. What was he thinking? I wondered if he was going home to say to his wife: You'll never believe what this Wall Street clown did at work tonight.

I no longer work on Wall Street and, for the record, I haven't had a drink in six years. But I remember from back in the day that sommeliers see and hear EVERYTHING.

So, I decided to check in with some of the city's sommeliers to find out what kind of dirt they might share. (On the condition of anonymity, of course — Wall Street traders are some of their best clients. They know which side their bread is buttered on!)

A sommelier from a downtown restaurant that is a staple in the Wall Street world said most of his finance clients pick a bottle of wine in the 75th percentile range — they don't want the most expensive bottle but they don't want to look cheap either.

Another sommelier, who works at a midtown restaurant popular with Wall Street traders, said sometimes a guy will come in the day before a dinner to talk.

"It's smart. Nobody wants to look indecisive when ordering in front of their clients," the sommelier said. "There's a big difference between the guy who knows what he's doing and the guy who reads the wine list like a research report."

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Andresr | Getty Images

I spoke to another sommelier, who has worked at several of New York's top restaurants and is currently at an Italian restaurant on the west side, and got him to tell me some of the craziest stuff he's ever seen.

What's the most expensive bottle you've ever sold?
It was just over $20,000. A Domaine de la Romanee-Conti. Any table that racks up a few thousand dollar bill is a great table!

It must be easier to sell when they're drunk.
The third bottle is the easiest for an up-sale.

What's the drunkest mistake you've ever seen at a business dinner?
The guy hosting got wasted. I mean really wasted. So much so that he didn't remember eating the last half of his tasting menu and demanded to be served again. No matter how much I or the people at his table tried to explain to him that it'd already been served. He didn't believe it. So we served it again. Everyone else at the table was horrified.

It's hard to argue with a drunk trader.
It really is.

What's the most "Wall Street" thing you've seen?
Well, I was flown to Cyprus to work at a 50th birthday party. I was told about the event three days before I needed to be there — and I only had to work one night. No expense was spared. The party was out of control — clowns, guys on stilts, belly dancers, marquee signs with flashing light bulbs. There was even a jail with a sheriff who locked people up for not having enough fun!

Have you ever gotten a stock tip?

It actually used to happen 15 years ago or so. Everyone had some Internet stock they'd share with you. I haven't gotten any lately. Why do you have any?

Save your money. That's my tip. What's the craziest question you've ever gotten?
What's your best wine over $10,000?

Wait… What?
They wanted a nice wine, but only if it cost $10,000 or more.

You should have suggested a $9,000 bottle.
Then I wouldn't be doing my job.

Commentary by Turney Duff, a former trader at the hedge fund Galleon Group. Duff chronicled the spectacular rise and fall of his career on Wall Street in the book, "The Buy Side." He's also a consultant on the Showtime show, "Billions," starring Damian Lewis and Paul Giamatti. Follow him on Twitter @turneyduff.

Catch Turney on the all-new season of CNBC's "Filthy Rich Guide," Tuesday nights at 10pm ET/PT (Starts Feb. 23).

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