Jeff Skilling was once president of a company that (claimed to) rake in over $100 billion annually. Now he’s had to kiss carbs good-bye (“You don’t want to get sick in here,” he said, as he talked about practicing yoga, walking four miles a day, and avoiding carbohydrate-heavy meals to stay fit) and beg reporters visiting him in the joint to buy him a cup of coffee.

Ninety minutes into our meeting, Skilling lowered his eyes to the floor. “I apologize for asking,” he said, embarrassment in his voice. “Could you buy me a cup of coffee? Inmates aren’t allowed to touch money or approach the machines. They could put me in solitary for a week.”

As I got his French-vanilla latte and recovered from astonishment that a man who had led a $110 billion company was not allowed to handle two quarters, I took the opportunity to get more personal, asking, “What is life like in jail? What is the scariest part of being here?”

You wanna avoid this fate, which likely also includes asking Bubba’s permission to have the night off? Skillings got some tips for avoiding unsolicited tips on the inside.

1. Don’t say shit.

Skilling now sees that testifying may have hurt his chances for an acquittal, but he thought it was a risk worth taking to be able to speak openly about what happened. In retrospect, it wasn’t.

2. Find a hack to write a piece telling people what a swell guy you are, who will ixnay on the whole eshay raudfray.

During the four years leading up to the trial, Skilling was visible in Congress and in the courtroom, but as a discredited CEO, he wasn’t focused on his standing in the public’s eyes. Looking back, he regrets not maintaining relationships with key industry advocates in and outside the media.

3. Realize that people don’t “get” us, or our sense of humor, and will likely it against us.

In May 2001, Skilling famously said, “They’re onto us” to a group of Enron executives about a negative analyst report on the company. Five years later he was defending himself by claiming that his comment was sarcasm, not an admission of guilt. Skilling nervously chuckled as he recalled when he was publicly edgy and impatient during the episode, but he quickly got serious and seemed self-reflective when he said, “Sarcasm is easily misinterpreted and can be a tremendous liability.”

Comments (21)

  1. Posted by Anonymous | June 14, 2010 at 12:32 PM

    Looks like he could benefit from some Bill Ackman prison warden humour. Just sayin’

  2. Posted by Stop Snitching | June 14, 2010 at 12:36 PM

    Anal-yst, or perhaps one of his many fans, is snitching on all of you guys on cluster…..

  3. Posted by Anonymous | June 14, 2010 at 12:47 PM

    If you have any questions about prison sex, feel free to send them my way.

    The Gay Banker

  4. Posted by Onlooker | June 14, 2010 at 12:59 PM

    @2

    Wasn’t me, although thanks for the heads-up so I could respond.

  5. Posted by Anonymous | June 14, 2010 at 1:02 PM

    @ Gay Banker: Are you the hamburger or bun, per se? Santorum?

    -Guy who is not gay, but wants to assess if Gay Banker is Jack or Jill

  6. Posted by Anonymous | June 14, 2010 at 1:04 PM

    French-vanilla lattes in prison are the new killin’ it.

  7. Posted by Curious Outside Connecticut | June 14, 2010 at 1:06 PM

    2, what’s the link?

  8. Posted by Anonymous | June 14, 2010 at 1:24 PM

    gimlet morning, bess?

  9. Posted by eli porter | June 14, 2010 at 1:28 PM

    Aint no wonder why he came out, he already in tha Gay Parade

  10. Posted by Anonymous | June 14, 2010 at 1:30 PM

    typo:
    “and will likely it against us”

  11. Posted by Anonymous | June 14, 2010 at 1:48 PM

    @5 – Baby I’m sell side.

    The Gay Banker

  12. Posted by Anonymous | June 14, 2010 at 2:15 PM

    Nymex’s “Man of the Year”………ah, those were the days.

  13. Posted by A. Vayner | June 14, 2010 at 2:24 PM

    @9 Like Rosie O’Donnell at a bisexual bridal shower

  14. Posted by Anonymous | June 14, 2010 at 3:10 PM

    Anal_yst go home.

  15. Posted by Anonymous | June 14, 2010 at 3:24 PM

    Desnt her make licence plates, chain-gang clean-up or something to earn cash for a cup of joe?

  16. Posted by Anonymous | June 14, 2010 at 4:36 PM

    An inmate can get coffee on the inside but not during visitation time. The federal facilities I visited when a friend was in such a “gated community” had vending machines that distributed several blended coffees and coffee drinks from a machine like “Cafe Vienna” etc. Also, they have microwaves and sandwiches from vending machines so you can have supper with an inmate. The seating is rows of plastic chairs (no tables) that you can’t move like to form a circle or somesuch so you have to sort of strain to look ahead at someone. You get to visit for about 2.5 hours if you wish. It’s pretty hard to come up withy 2.5 hours of conversation. The allow prisoners to take photos of an inmate with family or friends for a fee as I recall. While visiting my friend I did get to meet a former Governor of Louisiana who was a pretty nice fellow and always had many visitors. My friend was released after an 8 month stretch about 6 years ago.

    You have to be screened and vetted before the BoP will let you in. They tell the inmates not to have wives and girlfriends visit on the same day.

  17. Posted by Eli | June 14, 2010 at 4:54 PM

    I’m the best mayne

  18. Posted by Anonymous | June 14, 2010 at 7:18 PM

    How about making Skilling the next, special contributor? You could pay him in lattes.

  19. Posted by guest | June 14, 2010 at 7:46 PM

    @18 I like the cut of your jib.

  20. Posted by xtra chromo | June 14, 2010 at 8:35 PM

    TriG paLin

  21. Posted by Venerability | June 15, 2010 at 12:26 PM

    Sometimes I think there is no distinction between Markets and World of Warcraft!

    Please read “Blind Woman’s Bluff” http://wp.me/pVYiX-i

    “Of all the technical indicators around, none is as accurate at predicting market or sector turning points as the deliberate crashing of my computer system. If my poor little PC is weeping buckets of computer-tears and writhing in computer-pain – trust me, something wonderful or dreadful is about to happen to the markets.”

    (Dr. Ellen Brandt is founder of the Centrists and Media Revolution Groups at Linked In and the Centrists, Boomer Network, and Ivy League Twibes at Twitter. The former long-time business editor of a major US women’s magazine, earlier in her career, she served as a corporate investor relations manager and was a regional vice president of the National Investor Relations Institute.)

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