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Former Phillie Dykstra living high-flying life of an entrepreneur

Lenny Dykstra looks a tad different than he did during his tobacco-chewing days. (Jennifer Midberry/For the Daily News)
Lenny Dykstra looks a tad different than he did during his tobacco-chewing days. (Jennifer Midberry/For the Daily News)Read more

NEW YORK - A weary voice announces over the cell phone:

Change in plans, bro.

A real-estate opportunity he has had his eye on in New England looks like it could fall in place, so Lenny Dykstra, the owner of the voice, hops into the rear of a private car and heads out to Teterboro (N.J.) Airport. There, he ascends a foldaway stairway onto a corporate jet and arranges himself with his laptop in a leather seat. Someone brings him a cup of root beer, which he sips as the Hawker 800 begins charging down the runway, takes off, and settles into a cruising altitude of 11,000 feet. With a Gulfstream cap over his eyes, Dykstra nods off.

He has been up for 3 days. The day before, he flew in from California and landed in New York at 4:30 a.m. He spent the whole day talking with investors, then stayed up well into the following morning choosing photographs and overseeing layouts for an upcoming issue of The Players Club, a glossy magazine aimed at helping athletes invest their money. At 9:30, Wall Street began falling again on fears of a global recession. But Lenny set up the appointment to see that property in New England, 100 or so acres with water frontage that he hoped to develop into 40 luxury estates. Only asleep for a few seconds, he wakes up and glances out the window, beneath which slides a panorama of shimmering lakes embraced by vivid hues of autumn foliage.

"This property we are seeing is so unique there is probably just one like it in the whole world," says Dykstra, now chewing on a sandwich that was passed along to him. He taps the keys on his laptop, which he angles around and says, "Here, look at it."

A photo of the property pops up on his screen: An opulent estate sits at the center of a stunning landscape. Price tag: $15 million.

"Look at the house," he says. "I have been keeping an eye on it for a while. Owned by a cardiologist."

The plane begins to descend into the New Bedford (Mass.) Airport. Dykstra is asked how he discovered the property.

He flips his laptop closed as the wheels hit the runway and replies, "I am always hunting, bro."

Twelve years have passed since centerfielder Lenny Dykstra finished playing baseball at the age of 33. As he says now, he got out of it what he wanted: A World Series Championship with the Mets in 1986, and "I beat the bleeping Braves." That would have been with the "Macho Row" Phillies of 1993, the year he batted .305 in the leadoff hole and swatted four home runs in the World Series in a losing effort against the Blue Jays. With chewing tobacco jammed in his cheek, he played with a "Gashouse Gang" abandon until he could play no more. A bad back sent him to the showers 3 years later. When he thinks of those days now, it is not with regret that it ended so soon but with an appreciation.

"Baseball was a way out and up for me," he says. "It put me in a position to strike."


"Meaning," he says, "you have to have chips to play in the game."

Two days in New York with Lenny Dykstra is like circling under a wind-blown popup; you never know where he will come down. Right now - which is to say, 8 hours after deplaning back at Teterboro - he has landed in a lounge at the Ritz Carlton in Battery Park. A piano plays in the background as Dykstra clicks on his cell phone, which has a Merle Haggard ring tone and 39 new messages. Offhandedly, he says he has to call his wife Terri back in California; it is their wedding anniversary. On the cocktail table in front of him is a bag of Twizzlers licorice - red. Given his fixation with the stuff, it would appear to be his principal vice these days, a far cry from the Dykstra who one boozy evening with teammate Darren Daulton crashed his red sports car into a tree. Dykstra says he has calmed down since those days, during which the Mitchell Report claimed he had also used steroids. But even before that subject can come up in conversation, Dykstra warns: "No drugs."

Few who followed his exploits in the old days would have foreseen such an outcome for Dykstra, who during his wild youth figured to be 8-5 to end up face down on the poker table. But here he is, not just a wealthy ex-athlete but one with an entrepreneurial vision. With his baseball money, he opened up three car washes in Southern California, which he later flipped for $52 million. Along with the immensely successful "Nails on the Numbers" newsletter he produces for the - in which he recommends option plays for better than 1,000 investors for an annual subscription fee of $1,000 - he has placed a big bet on The Players Club, which is intended to provide athletes with a consortium of services ranging from annuities to jet-charter services. With an array of high-end advertisements, the magazine circulates on a nonsubscription basis to 25,000 players, agents, coaches and other insiders.

"At the end of the day, the magazine is about helping players," says Dykstra, who gnaws on the end of a piece of red licorice. "When your career is over, it is an abrupt end. Everything you have been and everything you have lived for is gone. There is nothing there. That is the reality. And you have to face that reality."

So how is Dykstra doing?

Ask him.

"Liquid crystal, bro," he says. "I am liquid crystal."

Even with the downturn on Wall Street?

He laughs and says, "I was born to make money."

He is told that some people are in a state of panic.

"They should be," he says. "Real estate became like art. People started placing crazy values on it. California has 50 percent of the bankruptcies in America. No other state has more than 2 percent. I know one clown who has a house up for sale for 25 million dollars."

And that would be . . . you?

He laughs: Yeah.

By his own accounting, Dykstra has a net worth of approximately $64 million. That includes the estate in Thousand Oaks, Calif., that was once owned by hockey legend Wayne Gretzky, and yes, it is for sale: 18,000 square feet, six bedrooms, 7 1/2 baths, two guesthouses, a pool, a spa, gazebo, exercise room, tennis court and a couple of two-car garages. He says the place is just too big for him and his wife, especially now that his oldest son Cutter has signed a pro contract with the Brewers. So he is "downsizing" into a neighboring $8 million estate he also owns: 8,100 square feet, five bedrooms, 5 1/2 baths, a pool, a spa and a four-car garage. According to his November 2008 financial statement, he also owns $750,000 in cars, $425,000 in jewelry and artwork, $540,000 in furniture and antiques and $225,000 in electronics.

Oh, yes . . . and then there are the planes.

Flying commercial is the very definition of hell for Dykstra, who says he has not done it in years. One of the chief components of The Players Club is providing access to private jets, which will be supplied by the company Dykstra oversees, "Legends Air." He has his own personal jet that has been in the shop since summer: The engines are being worked on and the interior is being redone. Dykstra himself is keeping a close eye on the progress, even down to the design of the dinner plates that will be used in the cabin. Someone handed him a sheaf of papers with patterns on it during the trip up to New England. He examined each carefully until he finally came to a decision.

"Here," he said, holding one of the patterns up for general inspection. "Look how classy this is."

The SUV picks up his traveling party at the New Bedford Airport. Dykstra slides into the backseat with the woman who owns the property not far from Martha's Vineyard. As her son swings out of the parking lot, she begins giving him an overview of it. "Martha's Vineyard, you have to be a blueblood to get in there?" Dykstra asks. Uncertain if he is joking, the woman hesitates and replies, "Oh, no, not these days." The woman adds that the place has been zoned for development, which is precisely what Dykstra has planned.

Overlooking a sloping expanse of fields is a charming estate, the dining room of which opens out on a tranquil garden. Dykstra and his entourage take a tour of the interior and then pile back into the SUV, which is now driven by the cardiologist. He powers the vehicle up over some fallen branches and into a clearing. There is a stunning view of the sailboats moored at the mouth of Buzzards Bay, which leads out into the Atlantic Ocean. The cardiologist parks and asks Dykstra to join him for a walk along the shoreline. As Dykstra stomps through the high grass, he looks as if he should have a shotgun slung across his arm and a pack of bloodhounds at his heels.

"Any animals up here?" Dykstra asks.

The cardiologist says, "Some deer. And we used to have some ostriches."

Dykstra absorbs that and asks, "Any bears?"

Someone says, "The bears are back on Wall Street."

He pauses and says, "Ha, yeah, I get it."

In the green room at Pier 60 in Manhattan the following day, Dykstra is dressed in a gray suit and blue-striped tie that is somewhat askew. "What do you think - I clean up good?" he asks. The slur is gone from his speech, which probably has to do with the fact that he has caught up on his sleep. He looks at himself in a full-length mirror, which reveals the beginning of a paunch as he unbuckles his pants and tucks in his shirt.

"You work out, Dude?" he asks a person in the room.

"Occasionally," he is told. "Not really, though."

"Me neither," he says. "My whole life I did. Man, I am sick of it."

He pauses and says, "What am I going to talk about?"

Dykstra is scheduled to give a speech to a group of investors for He says he is doing it as a favor for the owner of, Jim Cramer, who has done Dykstra the favor of promoting him as a budding stock guru. Editors at agree that Dykstra has emerged as a "real star" on their Web site, which is hard to believe given the fact that it was not that long ago that his idea of being financially speculative was drawing to an inside straight. But he has become adroit at picking stocks, famously so, in part because he had a big investment nearly wiped out in an economic downturn in 2002. The $2 million he had in his account had dwindled to $400,000.

"So I go to Wally Wall Street with his G.G. suspenders," he says. "And . . . "

G.G. suspenders?

"Gordon Gekko," Dykstra explains. "Remember him? 'Greed is good.' Great movie. So I ask, 'What happened to my money, bro?' "


"And I had no idea what he was talking about," says Dykstra. "It was humiliating. And I decided then and there that this would never happen to me again. I got 30 of these financial newsletters and I studied every one of them."

Some 300 people have crowded into the ballroom to hear Dykstra expound on his "strategy," which is essentially "a stock replacement system." Quite simply, that would amount to this: Say a stock is trading at $24 a share. Instead of buying 1,000 shares for $24,000, Dykstra will find a "deep in the money call" option to control a block of 1,000 shares for a time period of 6 months to a year out, which would require much less of a capital outlay than by buying the underlying securities. A Good-to-Cancel order is then placed at $1 higher than his purchase price, which would produce a $1,000 gain if and when the option price moves up $1. Dykstra then takes his $1,000 and moves on. He says he is always looking for "quality companies that have been beaten up," which is not hard to find in this economic environment.

"I always ask people, 'Who invested your money?' " Dykstra says. "And they never seem to know. I say, 'Who? Was there a person? Did you look him in the eye?' . . . This model will work in any market, because there are always going to be stocks that are undervalued."

Dykstra is 83-0 in his calls on "Nails on the Numbers," which is to say you would have earned better than $200,000 if you played along with him on But some have done even better than that. Bruce Cohn, of Seattle, is $300,000 in the black playing with Dykstra. "I doubled up on his positions and have deployed some of his strategies to select options myself," says Cohn, who points out that there "is always the potential for losses" when it comes to playing options. Cohn says that "83-0 speaks for itself." Mark Still, of Mobile, Ala., is so convinced that the system works that he says he walked away from a job as the portfolio manager at a bank to play it full time. Says Still, "What impresses me is if I have any questions he gets back to me."

But Dykstra is not so golden in the eyes of some others. A Manhattan-based accounting firm sued him to get its $138,000 for doing his 2006 taxes; Dykstra says he was overcharged. And he has been entangled in legal problems with Doubledown Media, the original publisher of The Players Club, stemming from what Doubledown Media claimed were unpaid bills. Dykstra says that issue has been resolved and that he is forging ahead with the magazine, a proposition that always experiences occasional growing pains. The October issue has tennis star Roger Federer on the cover and more than 200 pages.

"Each issue has gotten better," he says. "This is for the players. And sports are recession proof."

He is asked: You think so?

"I know so," he says. "You never run out of customers. Even in down times people still want to be entertained."

A crowd surrounds Dykstra when he is done speaking. He signs some autographs and he poses for photographs with some of his fans. Some of them ask him how he expects the Phillies to do in the World Series and he says he likes them. "They have a nice team," he says. But baseball is just a topic of idle conversation to him at this point, an easy reference point to segue into the affairs of chasing a dollar. "Baseball was always too structured for me," he says as he walks out in the parking lot. He grins and adds, "Guess you could say I was one of those miserable millionaires."

Evening has fallen as Dykstra climbs aboard the plane. The pilot closes the door and disappears into the cockpit. Someone hands Dykstra a cup of root beer. He flips open his laptop and checks his e-mails. He is disappointed with how the day has gone. The property was not what he had envisioned.

"It was not what I had expected," he says.


One of his associates replies, "It would be a tough place to develop. No sandy beach. No deep water port."

Dykstra adds, "It looked better online."

Eleven thousand feet in the air, he glances down at his computer screen and says, "The market got bitch-slapped again." Down more than 300 points, but better than it could have been given the way the day had started. Outside of his window, the lights of Manhattan shimmer in the distance as Dykstra nods off again. But he is only out for a few seconds and is wide awake when the plane eases down onto the runway. And as it does he says under his breath: "Round and round it goes. And where it stops nobody knows." *