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More bad news for Lenny Dykstra

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On May 1, I wrote about the news that TheStreet.com (NASDAQ: TSCM) had dumped Major League Baseball player turned pseudo options expert Lenny Dykstra.

Now The New York Post chimes in with more disturbing news about Dykstra's financial affairs. Dykstra has total debt of around $50 million and isn't paying up. He's being sued by a cavalcade of former business associates who claim he never paid them for services performed, and he even allegedly convinced a flight attendant to put a $10,600 flight on her credit card for him and then failed to reimburse her. He's being sued by his literary agent too, who says Dykstra never repaid him for money he lent him.

If the reports are even 2% true, Lenny Dykstra is a complete financial disaster, which raises an interesting question: Why did he have a financial advice column with TheStreet.com? In March of 2008, The New Yorker took a lengthy look at Dykstra's career as an options guru:

He began sending e-mails to Jim Cramer, the host of "Mad Money," on CNBC, with questions and tips. "My first reaction was that it wasn't Dykstra, that someone was just using his name because they thought it was funny," Cramer told me recently. "My second reaction was: 'My sister's a huge fan. Can I have your autograph?' He sent this huge poster that said, 'Nan, I love you.' " (Cramer's sister is named Nan.) Cramer eventually encouraged Dykstra to write a daily column for his financial site, TheStreet.com, and "Nails on the Numbers," one of the site's biggest traffic generators in recent memory, was born. Writing it typically took Dykstra all night. "Me and Mr. Thesaurus were, like, buddies," he said.

In other words, Lenny Dykstra got a job giving financial advice for TheStreet.com not because he has worthwhile financial advice and not because he's a great writer. He got the gig because of his celebrity and the fact that Jim Cramer's sister is a "huge fan."

TheStreet.com is deserving of a significant hit to its credibility as a result of this affair. The site played a big role in pumping Dykstra into the supposed financial wizard that he became, someone who appears to have left a lot of innocent people in the hole.

If you want a laugh, check out the trailer for a puff piece documentary about himself that Dykstra was apparently making last year.

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Last updated: November 24, 2009: 11:16 AM

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