Where did all that money go?


Beginning in 1986 as a 23 year old and ending in 1998 at the age of 35, Lenny Dykstra made $36,525,000 from his professional baseball career. All set for life, right? Dykstra would live with his wife and children in a nice house, play golf every day, show up at a few events every year to celebrate the Mets 1986 World Series title and live a quit and happy life secure with the knowledge that he’d never have to work or worry about money again.

Not so quick. Yesterday, Dykstra was sentenced to 3 years in California state prison for his part in a scam to lease high-end cars from dealerships by providing false financial information. Hey, the mortgage companies can do it, why can’t Lenny? On top of that, he faces uncertain bankruptcy proceedings.

Bankruptcy you say? How can that be? Doesn’t Dykstra have oodles of money in the bank from his playing days? Apparently not. Dykstra is also scheduled to go to trial this summer on federal bankruptcy charges. Dykstra sought bankruptcy protection claiming that he owed $31 million and had only $50,000 in assets. After filing for bankruptcy he is alleged by federal prosecutors to have sold or destroyed more than $400,000 of stuff from the interior or his $18.5 million mansion without the permission of the bankruptcy trustee. That is a big bankruptcy no-no. That also led the trustee to ask the bankruptcy court to deny Dykstra’s request for a discharge because he had acted in a “fraudulent and deceitful manner.” Adding to his downward spiral, Dykstra was accused of advertising for a house keeper on Craigslist and then when the women showed up at his house of exposing himself to them. Oh my.

How, pray tell, can a man earn $36 million in his baseball career, own five car washes that he sells for $51 million and then in less than 15 years be bankrupt? Here’s part of the story of how Lenny got there:

  • Buy Wayne Gretsky’s house for 18.5 million, hope to sell if for 24.5 million, but have it sold at foreclosure for 10.5 million
  • Hire pilots to fly you around in your recently purchased jet and don’t pay them
  • Start a charter jet company, serve as president of several privately held companies like car washes, quick lube centers and a real estate development company and clearly not understand how to run so many things at once
  • Start your own magazine called “Players Club” and ship 20,000 free copies to clubhouses and locker rooms around the country at a cost of about $500,000 per month
  • Become a stock picker because your baseball days made you a financial soothsayer and Jim Cramer thinks you are a stock market guru then market yourself as a financial genius to athletes yet garner no clients
  • Get sued about two dozen times
  • Borrow millions of dollars and don’t pay it back
  • Don’t pay your taxes

It all sounds rather, uh, dirty. A bit like Lenny when he was playing baseball.

What is the lesson here? One possible lesson: Dykstra got into spending habits that were not sustainable, that he began to live a lifestyle that got away from him and that he was not mature enough to deal with the huge amounts of money he earned during his career. That is the generous take on Dykstra’s behavior. Perhaps, he was too loose with his money and he really isn’t a bad guy. Or, maybe there is a darker side.

I don’t know a thing about Dykstra. I’ve never met the guy, never talked with someone who knew him and never had any kind of remote contact with him. The only things I know about him come from watching him play baseball and from what I’ve read. But, I think the stories behind Dykstra’s shenanigans, and there are too many similarities in all the stories of cheating and manipulation to ignore the strands of truth that run through them, suggest something darker about Dykstra – that he wanted and was obsessively driven by more than just money. He wanted continued adoration, notoriety and celebrity. The things he enjoyed when he was playing baseball. The intangible things that money can’t buy. He wanted the cheering crowds, the sycophants that draped themselves on him afterward and the power to persuade that often comes with celebrity. Dykstra spent all his money chasing his ephemeral baseball past. Now, he’s going spend three years in jail for that chase. His present looks pretty damn depressing and his future looks even more grim.


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