The Filthy Rich Guide

10 outrageous stories of Wall Street excess

On Wall Street we sometimes used the phrase "f-- you money." (I think we stole that term from the hip-hop community.) It's money spent that is financially offensive to others while perpetuating and maintaining an obscene lifestyle. And while I'm not proud of it, I was totally guilty of being that guy...

Catch Turney Duff on CNBC's "The Filthy Rich Guide," a show about how the .00001 percent spend their money. The show airs Wednesdays at 10pm ET.

Hundred-dollar bills falling from sky
Slava Gutsko | Getty Images

One of the most outrageous things I ever did was to make it rain at Madison Square Garden.

Back in my hedge-fund-trader days, I was invited to Morgan Stanley's luxury box for a Knick's game. The skybox is nice, but after your fifth visit, you realize it's just a wet bar with B-minus chicken fingers and some free Budweiser. So to entertain myself, I invited my cousin Ethan and Johnny Hong Kong, a professional drifter/filmmaker to come with me. I told Morgan Stanley I was bringing two interns. We got there just before tipoff.

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I was bored by the second quarter. I'd already made my rounds and was sick of talking about the biotech sector and the usual chit chat. So I peeked over the balcony to see where the real fans sat. I pulled a wad of cash out of my pocket, plucked out a five-dollar bill and released it over the balcony.

"What are you doing man?!" Johnny asked.

It floated down onto the right shoulder of a woman wearing a Ewing jersey. She spotted it immediately, quickly looked around and then snatched it and shoved it in her pocket.

We couldn't stop laughing.

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So, I start dropping a couple of one-dollar bills. Then $20 bills.

It was raining money and the fans became animals! The entire section looked up — they were hungry for more. In a matter of minutes, I tossed $300 over the balcony as Johnny and Ethan cheered in between the Morgan Stanley raised eyebrows. The crowd had forgotten about the game — all eyes were on us.

Then I started dropping $100 bills — people were boxing each other out better than the Knicks as the hundreds fluttered into their hands. $1,000 later, I was out of money.

Here's a list of some of the other outrageous financial stunts I have ever seen, heard about or participated in on Wall Street. This is my "Filthy Rich Guide to Wall Street."

Screw you, Corzine. Appaloosa founder David Tepper, who had been passed over for partner at Goldman Sachs by Jon Corzine, bought a $50 million beach house belonging to Corzine's ex-wife — just so he could knock it down and build a bigger one. He later admitted in an interview with New York magazine that he did it on purpose. "You could say there was a little justice in the world," he said.

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And he shall be called "Tammy." Just for fun, the head of a trading desk made an outstanding offer to all of the people on his desk: Anyone who legally named a newborn boy "Tammy" would receive a check for $25,000 upon submitting a valid birth certificate. Alas, no takers — it proved too difficult to get any mother to agree.

Yeah, there's an RV in the middle of our house. A Wall Streeter boasted that he and his kids loved to go camping, so when he built his Connecticut mansion, they bought and lifted a jumbo sized RV camper and placed it in the center of the basement — THEN built the house around it.

A nanny for the dogs. The wife of a hedge-fund manager demanded her husband hire a fourth nanny — just for their dogs.

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Drug dealer on the trading desk. A sell-side firm was having so much fun partying in the 80s, they put their drug dealer on the payroll as an assistant. It was more convenient to have him hanging out on the desk. The dealer ended up learning how to trade stocks and was good at it. Years later he became the head of the desk!

The Super Bowl of escorts. At a Super Bowl in New Orleans, a floor broker rented out the entire 11th floor of a 5-star hotel. He also rented out an entire escort agency. He put one to two girls in each room for his clients.

Happy Birthday from Usher. One Wall Street mogul threw a red-carpet-themed 40th birthday party for himself. Fake paparazzi were hired to make the guests feel like celebrities upon entering. There were Vegas-styled cocktail waitresses and circus acts with people flying in the air. Oh, and then Usher came out and played an HOUR-LONG SET.

Usher performing
Getty Images

Buying the bouncer. A trader paid a bouncer one year's salary to quit his job on the spot and be his personal bouncer for the night and take him to the bathroom whenever he had to go. His only job was to, "clear a lane." The next day the trader was asked why he did that. His answer? "I just felt like it."

The $27,000 strip-club bill. A sales trader and seven other guys racked up this five-figure bill in six hours. The next day, he didn't know how to expense it so he went straight to the CFO. The CFO had a hard time figuring out what to do. He ultimately decided to take every dollar of commissions until the debt was paid off. Oh, and he said, "Don't ever do that again."

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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," and is currently working on his second book, a Wall Street novel. He is also featured on the show, "The Filthy Rich Guide," which airs Wednesdays at 10pm ET on CNBC. Follow him on Twitter @turneyduff.