Jimmy Cayne Almost Died Trying to Save Bear Stearns

Photo: Patrick McMullan
"He decides he's going to get married," Cayne says. "And he's one of the guys that's dating Barbara Walters … He says to me, 'I've decided I'm going to marry Barbara Walters.' The very next day in the papers she's engaged to Merv Adelson. I never said a word. Now normally — you know, if it was one of my buddies — I'd say, you know, 'Pretty good call there, pal. You're marrying her, except that she's marrying somebody else … That's called bigamy.'"Other things he told Cohan:
• On September 11, when Bear's stock was nosediving after the implosion of two hedge funds; Cayne went into the hospital with a prostate infection. Doctors gave him a 50/50 chance of survival. He kept the whole thing quiet because he feared a public disclosure about his health could further damage the firm.
• Growing up, Cayne wanted to be a "bookie." Instead he drove a cab, sold photocopiers, and worked for his father-in-law's scrap-iron business. He came to New York with the aim of becoming a professional bridge player.
• When he met his now-wife, she told him to "get a serious job, or get a new girlfriend."
• He bonded with Alan Greenberg over their shared love of bridge, but he refused to call him "Ace" and billed those who used the nickname in his presence $100.
• He bonded with Joe Lewis, on whom he unloaded $860.4 million worth of shares last September, over "a shared love of gin rummy."
• Why he resigned in January: "The options were limited," Cayne says. "When you become roadkill, when you happen to have lost some weight and you're not really healthy, but you know one thing — you know that you have worked your ass off and you're not smart enough to know the answer — that's tough."
• He was late to the meeting where Bear decided to sell to JPMorgan because he couldn't find a private plane to take him to New York from Detroit, where he was playing in a bridge tournament. (He placed sixteenth.)
• He's sorry about all that, by the way: "I didn't stop it. I didn't rein in the leverage."
• But actually he doesn't think it was totally his fault. He thinks principals at Goldman Sachs, Paulson & Co., and Dallas-based Hayman Capital conspired to bring down Bear Stearns.
Then he was like, "Dude, you want a fresh-baked chocolate-chip cookie? I got some."
The Trials of Jimmy Cayne [Fortune]

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