Charlie Sheen and Lenny Dykstra: Dysfunctional BFFs

The surest sign of the star's implosion: he's become best friends with baseball has-been Lenny Dykstra. Randall Lane details how Sheen chose the only buddy more dysfunctional than he is.

Former MLB player Lenny Dykstra and Actor Charlie Sheen. (Photos by Getty Images; AP Photo)

The surest sign of the star’s implosion: He’s become best friends with baseball has-been Lenny Dykstra. Randall Lane details how Sheen chose the only buddy more dysfunctional than he is.

A telling facet of the Charlie Sheen train wreck popped up on talk radio on Thursday. Sheen phoned into The Alex Jones Show, itself a troubling sign—Jones leads the “Truther” movement that believes the 9/11 attacks were an inside job. Then Sheen patched in the man he declared was his new BFF: former Major League All-Star Lenny Dykstra, better known as “Nails.”

“We love each other unconditionally and with violence,” gushed Sheen before addressing Dykstra directly: “You’re one of the best dudes alive, bro.”

Dykstra returned the favor, with trademark classiness: “No, no, you are… The thing about you, Charlie—people don't realize how brilliant you are. And I'm not a guy who gets on his knees, if you know what I mean.”

And thus has Charlie Sheen again pulled off the unthinkable: He found the only person in Southern California more unhinged than he is.

I know of where I speak: Three years before Charlie became Lenny’s BFF, I served that role. When I met him, Lenny was positioning himself as the financial guru for pro athletes. He had made millions from a car wash, and Jim Cramer had given him a stock-picking column on his website, He flew around in a Gulfstream IV, and had just plunked down $17.5 million for Wayne Gretzky’s L.A. mansion. Now Lenny hired me and my company to produce a magazine and website, The Players Club, that would promote fiscal discipline for jocks.

It’s like Paris befriending Lindsay. Ahmadinejad palling around with Gaddafi. Mel Gibson hooking up with… Charlie Sheen.

As Lenny promptly advanced $200,000 on a contract that would pay us up to $4 million a year, it became my business to help his business, even if that meant round-the-clock babysitting. For six dysfunctional months, Lenny called me a dozen times a day to help plot his businesses, carp about his family, or shoot the breeze.

Being Lenny’s rent-a-friend carried benefits, such as the time he insisted on flying me to Mexico on his private jet for my brother-in-law’s bachelor party. But mostly, there were pitfalls: business meetings where he’d fart loudly to make people uncomfortable, dinners where he’d order a fancy prawn dish and then berate the staff because the kitchen “forgot to peel the shrimp,” awkward staff meetings filled with increasingly foul racist and sexist slurs. By the end, he had given me a front-row seat at one of the great financial meltdowns in recent history.

For those new to the Lenny Dykstra soap opera, let me offer a brief synopsis that spans the three years between when I dumped him and Sheen picked him up. In that time, Lenny: stiffed me, my company and a few hundred other creditors; was sued two dozen times; had his jet repossessed; dragged his mentor, Jim Cramer, into an alleged pay-to-plug stock scandal; had his Gretzky mansion repossessed (but not before the fixtures were ripped out, and feces was strewn across the floor); had his wife file for divorce; and finally, filed for bankruptcy, listing $50,000 in assets against $31 million in liabilities. By last year, he was living in his car. (For those who want the longer version, Lenny dominates three chapters of my book, The Zeroes: My Misadventures in the Decade Wall Street Went Insane.)

In other words, Sheen has found a best friend that makes him look like a responsible voice of reason. It’s like Paris befriending Lindsay. Ahmadinejad palling around with Gaddafi. Mel Gibson hooking up with… Charlie Sheen. In fact, the more I examined it, the more these two seem clear soul mates. Consider:

Respect for Women: Like Sheen, paying to spend the evening with porn stars seems to be Lenny’s new dating MO. In December, Radar reported that Dykstra paid $1,000 to hang with adult film star Monica Foster. The only real difference between the two, stylistically: Dykstra’s check bounced.

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Family Relations: Sheen allegedly threatened to kill his one wife, Denise Richards, and held a knife to the throat of another, Brooke Mueller. Lenny’s damage is more cash-based, and more widespread. His brother sued him for breach-of-contact, claiming Dykstra cut him out of his rightful stake in the car washes. He used his mother’s credit card to buy $23,000 worth of jet fuel when his soon-to-be-repossessed jet was stranded in Cleveland. His son gave him his bonus when he signed with the Milwaukee Brewers—based on bankruptcy documents, that money was squandered. And when his wife divorced him, he described his thoughts this way: “war.”

Work Relations: Sheen yesterday expressed “violent hatred” toward the “fools and trolls” that helped him make tens of millions on Two and a Half Men. Dykstra, meanwhile, has been named one of the 10 worst bosses of all-time and twice faced accusations of sexual harassment. I actually watched him get gleeful whenever he had to fire someone, pantomiming that he was performing euthanasia, telling his victims to “breathe deep.”

Sleep: That manic tone in Sheen’s voice? “I don’t sleep,” Sheen told Alex Jones. “I wait.” The talk show host chortled in agreement, describing 3 a.m. texts he gets from Sheen. On Planet Lenny, meanwhile, a single day can encompass an entire week: I’d watch him stay up Monday through Friday, and then hibernate on weekends, a seven-day marathon turned into a single body cycle.

Love of Baseball: Finally, one area where these new best bros can bond in a manner the rest of us can relate. Dykstra was in the Major Leagues; Sheen starred in Major League. In fact, the pair recently had a big baseball powwow, with active and retired players like Brian Wilson and Eddie Murray. Lenny told Alex Jones that he and Sheen were playing catch— “long toss”—to limber up for the possibility of a film sequel, Major League 3.

That reminded me a story Lenny often told me. Growing up, he didn’t have any friends. (He’s an admitted misanthrope.) The only reason he ever got one, he says, “is so I’d have someone to play catch with.” That’s what I did, figuratively, for six months. And apparently what Sheen is, literally, doing right now.

But catch with Lenny tends not to end well. I dumped him after he stopped paying his bills. We sued each other before he eventually agreed to fork over $200,000 to cover various out-of-pocket vendors. He never paid, of course. His BFF after me, a California entrepreneur named Richard O’Connor, eventually reached out to me to help Lenny get an intervention. Not interested, I told him. O’Connor got stiffed, too.

So watch out, Charlie. Even at rock bottom, there’s another level below.

Randall Lane is editor at large at The Daily Beast. The former editor in chief of Trader Monthly, Dealmaker and P.O.V. magazines, and the former Washington bureau chief of Forbes, he is the author of The Zeroes: My Misadventures in the Decade Wall Street Went Insane.