The Fall of Lenny Dykstra

He won the World Series with the Mets, was a three-time All-Star with the Phillies, and then turned himself into a multimillionaire and financial guru. But it all fell apart in a pool of debt and drugs. How did the grittiest player in baseball end up bankrupt, friendless, and rotting in jail?

He won the World Series with the Mets, was a three-time All-Star with the Phillies, and then turned himself into a multimillionaire and financial guru. But it all fell apart in a pool of debt and drugs. How did the grittiest player in baseball end up bankrupt, friendless, and rotting in jail?

On a warm, nondescript Southern California night in January 2009, Dorothy Van Kalsbeek found herself driving out to the Camarillo Airport, hoping—against all logic—for the best, steeling herself for the worst. Nearly three years had passed since she accepted her present accounting job, and through the myriad emotional, mental, and financial trials, she had always believed her boss, her friend…would find a way out of this mess. Family members deemed him dead to them—yet Van Kalsbeek stuck. Former business associates sued him for millions—yet Van Kalsbeek stuck. Newspapers and magazines mocked him; former major league teammates ignored him; his wife left him—yet Van Kalsbeek stuck. Even as he lost the $17.5 million mansion and the $2 million Gulfstream jet and the $160,000 car; even as his business holdings vanished…Van Kalsbeek stuck. Hell, the woman hadn’t received a paycheck for her accounting services in more than a year.

“What can I tell you?” she says. “I believed in Lenny Dykstra.”

On this night, however, her faith was finally shaken. Dykstra, a former All-Star outfielder with the Mets and Phillies who, after his retirement, had been hailed by Jim Cramer of CNBC’s Mad Money as a financial wizard, had asked her to come to the airport for a chat. As she entered Dykstra’s lavish 5,000-square-foot second-floor office, Van Kalsbeek was struck not by her boss’ somber mood but by the item he placed at her feet: a black duffel bag, six feet in length. “It was enormous,” she says. “And it was stuffed.”

Inside it were hundreds upon hundreds of envelopes. Inside the envelopes were hundreds upon hundreds of bills. Unpaid bills. “Do me a favor,” said Dykstra, his spirits as low as his credit rating. “Go through these and tell me where I’m at.”

For the next three weeks the bag sat on her living room floor, unopened and untouched. “I was in denial, but I knew what was inside,” she says. Finally, confronting the inevitable, she sorted through it, bill by bill by bill. When she reported back to Dykstra, the news was grim.

“You have nowhere to go,” she said. “You’re broke and you owe millions.”

With that Dorothy Van Kalsbeek returned home. And cried.

As this story is being written, Lenny Dykstra—“Nails” to millions of baseball fans—is not Lenny Dykstra. He is inmate No. 2766176 inside the Los Angeles County Sheriff’s Department Men’s Central Jail. On June 6, 2011, inmate No. 2766176 was arrested for 25 misdemeanor and felony counts of grand theft auto, filing false financial statements, and possession of cocaine, ecstasy, and the human growth hormone Somatropin. He pleaded not guilty to the charges. While his ubiquitous orange jumpsuit disguises him as merely another of the facility’s inmates, unlike 99 percent of them, who dine together and sleep in enormous halls packed tight with bunk beds, inmate No. 2766176 is confined to his cell for 23 hours a day. His space, an approximately 8’x6′ block of stone, is equipped with a toilet and a sink. Meals are passed beneath a steel door. The tobacco, alcohol, and drugs he craves are not allowed; the laptop he addictively types on is miles away. Thanks to years of chewing, he has three or four teeth remaining in his mouth—brownish nubs jutting out from blackened gums. For companionship, he shouts to neighboring captives, none of whom he can see. Twice a week he receives a 15-minute phone call. Save for Van Kalsbeek, he has no one to reach out to.

The professional sporting landscape has forever been littered with the carcasses of punctured heroes. Yet save for the precipitous plummet of O.¿J. Simpson some 17 years ago, no jock in modern lore has traveled a rise-and-fall path quite as jarring—and oddly riveting—as Lenny Dykstra.

He was, not all that long ago, the poster child for the uniquely American ideal that dreams, buttressed by grit and determination, can actually come true. Raised in the working-class Anaheim, California suburb of Garden Grove, Dykstra—the second of three boys—was the prototypical short, scrappy kid who snarled and cursed and refused to be denied, an approach to the game that later won him the nickname Nails. From the earliest of ages, little Lenny told anyone who would listen that one day he would play major league baseball. Nobody listened. “He was always under­estimated,” says Brian Dykstra, his older brother. “People didn’t take Lenny seriously, because he didn’t look all that imposing.

But he was a pain in the ass who never took no for an answer.”

The Dykstra kids were raised by their mother, Marilyn, and stepfather, Dennis Dykstra, a blue-collar phone company employee. (Their real dad, Terry Leswick, abandoned the family when Lenny was four.) Dennis encouraged competitiveness, and Lenny spent his boyhood excelling in every imaginable sport. Yet baseball was his calling. The Dykstras lived in the shadow of Anaheim Stadium, and on the afternoons of Angels games the boys would ride bikes to the ballpark, slide beneath a gate, and romp around the outfield. “It was heaven,” says Brian. “We’d dive after balls, pretend we were real Angels. Then the ushers would kick us out. But for 15 minutes it was living a dream.”

Over his four years as an outfielder/pitcher for Garden Grove High, Dykstra emerged as Orange County’s best prep ballplayer. He batted .550 and entered the June 1981 amateur draft absolutely certain his hometown Angels would select him in the first round. Instead, they took shortstop Dick Schofield. The first round passed. The second round passed. Finally, with the 315th pick in the 13th round, the lowly New York Mets took a shot.

Dykstra was livid. “‘Fuck the Angels,” says Brian. “That was his attitude from that day forward.” The pain never left.

The Mets offered Dykstra a $25,000 bonus, good money for a 13th-round pick. He said no. They offered $27,500. No, again. $30,000—still no. “I’m the best fucking player in the draft,” he told Roger Jongwaard, a Mets scout. “I should be paid like it.” Finally, New York offered $35,000—take it or leave it. He took it. Hence, it was in the Podunk minor league town of Shelby, North Carolina that the curious legend of Lenny Dykstra began.

“He was the hardest-playing athlete I’d ever seen,” says a minor league teammate, who requested anonymity. “But he was very disrespectful, and he didn’t give a shit if he had to run over you to gain an edge. It was all about Lenny, Lenny, Lenny.”

Dykstra was a cartoon character brought to life. The anonymous teammate recalls he would sit on his bed and stuff his hollowed-out bats with cork (a precursor to his alleged PED usage in the ’90s). He’d bring home the fattest, ugliest women, have sex with them, kick them out, and return an hour later with another. Upon being drafted he bought a white Porsche 911 and rarely thought twice about driving 130 mph. Though he was bad at poker and worse at golf, he never turned down a bet. “I used to kick his rear up and down the golf course, but Lenny refused to play without having a bet out there,” says Marlin McPhail, a minor league teammate. “There was no reason for him to bet me, because he couldn’t possibly win. But he needed to have a stake on everything.”

On May 3, 1985, Dykstra made his big league debut, as the Mets center fielder. Although he had dreamed of being an Angel, New York was the perfect place for the scrappy 22-year-old with a thirst for attention and a love of the fast life. First baseman Keith Hernandez forced Dykstra to smoke cigarettes. Pitchers Doug Sisk and Jesse Orosco welcomed him into their back-of-the-plane beer-fueled poker games. Dykstra’s rep was secured when, while preparing to play golf at the prestigious Nassau Country Club in the summer of 1986, he walked past a gaggle of priests in the clubhouse, lifted a leg, and farted. “He fit in as well as anyone,” says Sisk. “Lenny was gritty and disgusting. So were we.”

When New York won the 1986 World Series, coming back to overcome Boston in a classic seven-game thriller, Dykstra established himself as a Big Apple favorite. Though he lacked the talent and résumé of the legendary Pete Rose, Dykstra was often compared to Charlie Hustle for his balls-to-the-wall approach. (In modern speak he’d be the equivalent of Boston’s Dustin Pedroia.)

Yet he also hovered close to the dark side. The Mets were a team of heavy drinkers and cocaine users, and Dykstra indulged in both, friends say. “Lenny had no limits,” says Ed Hearn, a catcher with the club. “None.”

When the Mets traded Dykstra to Philadelphia midway through the 1989 season, Shea Stadium loyalists were incensed. How­ever, his seven and a half years with Philadelphia told the story of a man burdened by demons. Though Dykstra was a three-time All-Star and helped Philly reach the 1993 World Series, he served as an ode to poor judgment. In 1991 he was placed on probation for his gambling problems, and then nearly died when—driving drunk—he crashed his car into a tree. And throughout his seasons in Philadelphia he—apparently, though he denied it—loaded his body up on steroids and growth hormones, emerging as the embodiment of the blatantly juiced athlete. “It was a joke, seeing how big he got,” says Hearn. When, in 1998, his body finally broke down—he’d been sidelined two seasons with injuries—he announced his retirement at age 35.

“Everyone in baseball thought the same thing about Dykstra—that he’d vanish and never be heard from again,” says Brian Johnson, a longtime major league catcher. “There was no reason to think he’d amount to much of anything.”

Ever since Lenny Dykstra was a young boy, people looked him over—the dirty uniforms, the foul mouth, the recklessness—and reached the same conclusion: This guy puts the D in dumb.

So what if he had been an A and B student in high school? So what if he could read most people in a second’s time? So what if, despite his love for the fast life, he had actually saved much of the money he’d made during his 12-year career? Lenny Dykstra was a buffoon—no ifs, ands, or buts.

“That perception,” says his brother Brian, “pissed Lenny off in a major way. He always felt he had to prove himself.”

Hence, in 1993, with his career coming to an end and his will to succeed as strong as ever, Lenny Dykstra looked around Southern California and sought a way to apply his competitiveness and drive to a different arena. Enter: executive car washes.

To Dykstra the idea seemed laughably simple. In 1994 the American economy was booming, and the beginning of the tech bubble was turning much of Orange County into a fountain of big money, big houses, and, best of all, fancy automobiles. Yet most of the car washes were dumpy, grade-C setups. Not Lenny’s. Within nine years his three SoCal-based car wash/quick lube establishments (a.k.a. “Lenny Dykstra’s Car Wash”) were grossing millions. Yes, a treatment at Dykstra’s cost three or four bucks more than at competing businesses. But unlike their owner, the Dykstra establishments were all class. He loaded up the buildings with baseball memorabilia and saltwater fish tanks; he insisted free coffee always be available. “The columns at the gas station were painted every day,” says Van Kalsbeek. “He had the pumps waxed every day, and if anything got scratched it was immediately replaced. You could show up any morning and you’d think it was the grand opening.”

Around the same time he was immersing himself in the car washes, Dykstra observed that his once-robust stock portfolio had taken a dramatic downturn. Upon retiring from the Phillies, he had divided $2 million into three different investment accounts. By 2002 that sum had dwindled to $400,000. Never one to sit down with a newspaper or book, Dykstra committed himself to learning how to invest: following the markets like a seasoned broker, purchasing his first laptop and addictively stalking the Internet.

By 2006 Dykstra opened his own trade account and was hired as a stock-market columnist for, a site cofounded by Jim Cramer. In 2008 Cramer raved about Dykstra’s stock-picking skills to HBO’s Real Sports. “If I didn’t know any better, I’d tell you that everything you hear from Lenny is an act, because there’s no way you’d ever feel like he’s as smart as he really is,” Cramer said. “He’s one of the great ones in this business.” Shortly thereafter, The New Yorker’s Ben McGrath wrote a glowing six-page profile titled “Nails Never Fails: Baseball’s Most Improbable Post-Career Success Story.” By 2006 he owned three car washes, a shopping plaza, and a gas station, was building a retail center, and was as famous for his financial wizardry as he had been for his diamond glory.

It all seemed too good to be true.

Read Part II