Madoff vs. Skilling: Who Would Win THAT Prison Brawl?

It’s the stuff headline writers’ dreams are made of: Bernie Madoff gets into a prison brawl.


Well, I have to take a little issue with use of the word “brawl” — it was really two old guys shoving each other. It wasn’t a good old-fashion prison beatdown like the one Allen Stanford got — a concussion, broken nose and two black eyes.

Still, you have to admit, it was pretty AWESOME.

And, of course, all this comes as the former Enron CEO Jeff Skilling, currently serving 24 years for his role in one of the biggest corporate frauds in history, gets his day in court — the Supreme Court — which means he could walk after all.

That convergence sparked some newsroom discussion: Why hasn’t Skilling ever been involved in a prison brawl? Furthermore, if he was, would he win?

Natch, that, led to a Prison Fantasy League: If Bernie Madoff and Sanford Allen got into a prison fight, who would win?

(Eh, probably Madoff. I’ll bet Sanford fights like a girl. All flapping hands and whatnot.)

OK, ok, what about Madoff vs. Skilling? You’ve got the scrappy New Yorker vs. the explosive energy chief.

We present to you: THE PRISON FANTASY LEAGUE. Six contenders, five matches. You vote!


Bernard Madoff
Bernard Madoff

Bernie Madoff: 71 years old. From New York. Serving 150 years for one of the largest Ponzi schemes in history that swindled hundreds, including quite a few celebrities—even Kevin Bacon.

Fun fact: Obsessive compulsive. Insists on smoked salmon sandwiches. No round edges tolerated.

Allen Stanford
Allen Stanford

Allen Stanford: 59 years old. From Mexia, Texas. Knighted for his public service and philanthropy in Antigua, where, coincidentally, he is accused of running a massive Ponzi scheme. Currently being held at a detention facility in Conroe, Texas. Faces life in prison if convicted.

Fun fact: Got a prison beatdown recently that left him with two black eyes.

Jeff Skilling: 55 years old. Born in steel country — Pittsburgh, PA. Serving 24 years for the Enron scandal, one of the biggest U.S. bankruptcies in history that left most of his employees penniless. Supreme Court has agreed to hear his appeal.

Fun fact: During his entrance interview to Harvard Business School, they apparently asked him if he was smart, to which he replied: “I’m f-ing smart.”

Martha Stewart: 68 years old. Born in Jersey City, NJ. Found guilty of lying to prosecutors over her sale of ImClone stock. Served five months in a federal prison camp while her appeal was pending. The facility, dubbed “Camp Cupcake,” is in West Virginia.

Fun made-up fact: With those mad arts and crafts skills, we’ll bet she can whittle a mean shank.

Bernie Ebbers: 68 years old. Born in Edmonton, Alberta, Canada. Founder of WorldCom. Convicted of fraud and conspiracy that cost WorldCom investors $11 billion. Currently serving 25 years at a federal prison in Louisiana.

Fun fact: Held the title of biggest corporate scandal in U.S. history, until Madoff came along and swiped it from him.

Dennis Kozlowski: 62. Born in Newark, NJ. Former CEO of Tyco. Serving 8.25 to 24 years for swindling $81 million from the company in unauthorized stuff.

Fun fact: Paid $1 million for a toga-themed birthday party for his second wife on the Italian island of Sardinia, featuring an ice sculpture of the famous statue “David” — only this one was urinating Stolichnaya vodka.

THE MATCHES: Slideshows:

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