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Lenny Dykstra - Tough and as Smart as Nails

This ex-baseball player is so dim, it’s hard to say whether he knew he was going to jail, even when he was sitting in front of a judge being told he was going to jail.

Lenny Dykstra, when he played for the Mets and Phillies, was a smarter player than most fans at the time gave him credit for, though that doesn’t make him a genius or a criminal mastermind or anything. To wit: On Monday, he was sentenced to three years in state clink for using phony information and a fake business to buy cars with money he didn’t have—a small-time criminal scheme that was one more step in the progression of one of the alternatingly most engaging and terrible athletes of the last 30 years, and a coda—perhaps—to one of the strangest and gaudiest post-playing careers since Lynn Swann flamed out on the political circuit.

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Dykstra was a late-round pick with a playing weight of 160 pounds who parlayed a keen batting eye (he had a higher on Base Percentage and a better strikeout-to-walk ratio than Hank Aaron) and less-celebrated methods of self improvement into a decade-long big league career and $36 million in salary. He was traded off the late-80s Mets team for being too wild—that’s like being kicked out of the Cro-Mags for being too tough—but helped Philly to a World Series. He wasn’t exactly media-friendly—he spoke like an insomniac boxer on dust, and looked a bit worse than that—and the keen-eyed, brain-damaged squirt looked like he’d be the first of his teammates to the poor house. He ended up doing very well, at least at first.

He retired to California, where he was from, and opened up a car wash, then another—“a business that couldn’t be replaced by a computer chip,” he explained to the New Yorker at one point. Somehow he became a successful investor. He trumped the short-sell method, and wrote columns about it. He sat on various boards and owned stores, and by 2008 his net worth was around $58 million. By then, he had bought Wayne Gretzky’s house and was praised by Jim Cramer—who used to have a reputation, remember—as a dynamite analyst. There seemed to be plenty fishy about Dykstra, but there was no rule the rich had to be trustworthy, and he didn’t seem worse than a lot of the other guys making bank at the time. Dykstra also tried his hand at publishing with Player’s Club, a glossy mag for pro athletes that somehow involved a charter jet company and financial advice. The magazine seemed an overreach, and after some bad publicity, folded. (Full disclosure: I interviewed for an editorial position there and the office was a dank, sad mess.)

There’s not enough room here to go into the lower points of Dykstra’s retirement, suffice it to say they involve charges of sexual assault, casual racism, missing toilets, and a son named Cutter. Pretty soon, you had to add an asterisk to all his past achievements: For baseball, steroids. Then his brother accused him of cutting him out of car wash money when he sold the company, then the bank foreclosed on Gretzky’s house, which he made a spectacular mess of. Then his magazine went belly-up and didn’t actually pay any of its employees; he sold his Mets championship ring and was swimming in debt by 2009… oh, and the short selling Dykstra was such a fan of may have ruined the country.

Dykstra was famously described in Michael Lewis’s Moneyball as having the sort of perfect idiocy—or Zen state of being, not sure—to succeed in baseball. He didn’t give a shit who he was facing, even if it was a Hall of Famer like Steve Carlton (who he hit over .400 against). That same lack of self awareness has been apparent ever since, but it hasn’t been helping him. He’d been charged for a variety of crimes over the years, but never got more than a slap on the wrist or a lien or two. It’s hard to say whether he knew he was going to jail, even when he was sitting in front of a judge being told he was going to jail. On the day of his sentencing, a note posted on his site, Nailsinvestments.com, urged readers to invest in Halliburton.

@samreiss_