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A former athlete, especially one with Lenny “Nails” Dykstra’s background (no college education, poor upbringing, etc), is not supposed to be able to do the things Lenny did after he retired from baseball. Many players eventually just gravitate back to the game they love, becoming coaches, broadcasters or front office executives. If you had only known one profession your entire life, would you want to do anything else after your playing career? Many other players end up out of the game with nothing to fall back on, especially once public appearances and autograph signings become less and less frequent. Some players end up far worse, never able to recapture the feeling they got from being out on the field, but never able to give up on searching for it again either. When Lenny retired, it seemed he had everything under control.

Lenny was a true rarity. A successful athlete who retired, left the game entirely, and reached levels of personal and financial success that few could imagine in their wildest dreams. For a while, he truly seemed to have the golden touch. From his chain of successful car washes, to his incredibly intelligent and lucrative investments, to a high-end charter company and magazine geared towards offering financial advise to professional athletes, everything Lenny touched seem to turn green (money, hello). He made money hand over fist, and was reportedly worth $58.6 million in 2008. He was even profiled in the New Yorker magazine and on television shows such as HBO’s Real Sports with Bryant Gumble.

So how did it all come crashing down? You’ll find out, but first we need to see how it all came together.

Lenny the Baseball Player:

How could Mets fans not love Nails?

To those who really followed his career closely, perhaps the fact that he was successful after sports wasn’t as surprising as the way he achieved that success. Afterall, Lenny’s work ethic was what made him the player he was throughout his career. lists Dykstra at 5’10” and 160 lbs. I would imagine that was his playing weight during his time with the Mets, as he got a little bigger when he played in Philly (more on that later). The Mets took the Californian in the 13th round of the 1981 draft, and he literally hit the ground running. In his first full season in the minors, Lenny stole 77 bases. The next year, he stole 105. He also added 132 runs, 105 walks and a .358 batting average. Not bad for a 20 year old.

In 1985, the Mets finally brought him up, and he quickly became a fan favorite because he played the game hard (and always with a big wad of chew in his cheek) and seemed to shine when the pressure was on. For example, Lenny had 81 career home runs in 4,559 regular season at bats (one HR roughly every 56 ABs). In his playoff career, “The Dude,” as he was also known, hit 10 round trippers in 112 at bats (one HR about every 11 ABs). Basically, he was five times more likely to homer in the playoffs than in the regular season. Talk about clutch. In 1986 alone he hit a walk-off home run in game three of the NLCS against the Astros, and a leadoff home run in game three of the World Series against the Boston Red Sox (2 total in the series). Lenny and the Mets went on to win that World Series, thanks in part to terrible Bill Buckner.

In 1989, the Mets angered many of their fans when they traded Dykstra to the Phillies, along with Roger McDowell, for Juan Samuel, one of the worst trades in Mets history (Samuel hit .228 that season and was traded for no one good that off-season). In 1990, for the Phillies, Dykstra had one of the best seasons of his career, hitting over .400 until late June (he ended up at .325) and posting then career highs in runs, hits, RBI and steals. Injuries cost Dykstra some time in 1991 and 1992, but 1993 was his real coming out party. He led the league in runs, hits and walks, and finished second in the MVP race. He also led the Phillies to the 1993 World Series, where he hit .348 with 4 HR as the Phillies lost to the Blue Jays.

Lenny Builds his Empire:

If the Dykstra success story ended there, I think everyone would have been happy. Everyone but Lenny, that is. He took that same work ethic and tenacity from the baseball diamond to the business world and stuck gold. As I mentioned before his successful business ventures included a chain of car washes, a day trading enterprise that garnered him millions in profits, a luxury jet chartering company for athletes, and The Players Club, a magazine for professional athletes that advised them on all things financial. In all, he was worth nearly $60 million dollars, had a beautiful wife, and everything else a guy could ever want (including living in Wayne Gretzky’s old mansion). As they say, however, all good things must come to an end.

After baseball, Lenny still appeared to have it all.

That saying really rings true with Lenny, because all of his good things pretty much came to an end all at the same time. It’s a bit ironic that Lenny’s last real business venture was a magazine designed to save pro athletes from the pitfalls of life after sports, mainly the financial pitfalls. As you read this today, Lenny Dykstra is broke and in jail. I don’t think he qualifies as the typical ex-professional athlete who loses it all because he did so well for so long after his career ended, but still… pretty ironic.

Where do we start with Lenny’s downfall? How about in 2007, with the release of the Mitchell Report, an investigation into steroid use in professional baseball in the 1990s and early 2000s (the “steroid era”). Even before the Mitchell report was released, it really was no secret that Lenny did steroids. When he showed up in Spring Training with the Phillies one year with 30 extra lbs of muscle, he attributed it to “really good vitamins. (” He has never admitted his steroid use, but his inclusion in the Mitchell Report kind of confirmed what everyone already thought. So Lenny was slightly disgraced, but he still had his beautiful wife, and his millions of dollars… doh.

The Fall of Lenny Dykstra:

Somewhere along the way, The Players Club, a magazine that was meant to save athletes from financial downfalls, crushed Lenny Dykstra’s own financial empire (his $17 MM house purchase in 2008 didn’t help either). By 2009, the magazine was a revolving door of employees who often left being owed months of back pay by Dykstra. Lenny also let unpaid bills stack up, like the $40,000 he owed to Getty Images when they stopped doing business with the magazine, and the $139,000 he owed to a midtown accounting firm (settled in court). At one point, Lenny said he was losing about $500,000 per month on the magazine, but he didn’t care because he wanted to help athletes (

Later in 2009, Lenny’s wife of 23 years, amid his financial turmoil, decided to file for divorce against him. Apparently this came after a few years of a “sham” marriage, in which the two slept in separate beds for “three or four years.” ( Tough time to leave your husband if you ask me, but from what I’ve read, I get the feeling it was more of a “fed up with things” divorce than a “no money, no love” divorce. Either way, sucks for Lenny.

Lenny needs to be tough as “Nails” where he’s going.

So where is Lenny now? He is divorced, his giant mansion is in foreclosure, he’s tens of millions of dollars in debt and he’s in jail. Wait, jail? Yes…jail. Why, you ask? Here’s a few of the reasons… In early 2009, Lenny filled a truck with furniture and other things from his foreclosed home and sold them at a pawn shop (among other items he sold or destroyed from the home). This is considered bankruptcy fraud, or bankruptcy embezzlement. Lenny faces five years in federal prison for this. But wait, there’s more! Lenny was also arrested in connection with possibly trying to buy a stolen car at his home in Encino, CA. He also tried to lease cars illegally with false documents and identities… Oh, Apparently, he also was found with ecstasy, cocaine and the human growth hormone, Somatropin ( In all, Lenny is up against twenty-five different charges and his bail is set for $500,000. It is safe to assume he’s probably going to prison soon (his trial begins on August, 9th).

Will Lenny ever rise again? The odds are definitely stacked against him, but this country is all about second chances. If he does go to prison, success is only one good investment away when he gets out. I, for one, would never count “Nails” out. Maybe he’ll create a magazine for retired athletes that shows them how to survive jail! His cell-mate Bubba could even write a weekly column on how to not become a jailhouse bitch! All kidding aside though, If anyone can come out from all of this on top, it’s Lenny. I really hope his story ends happily, and without too much jail time. Afterall, he has to be out to watch the new generation of Dykstras trying to make it big in baseball. His son Cutter (22) is currently playing in the minors for the Washington Nationals, and his other son Luke plays high school baseball (Lenny told the New Yorker in 2008 that Luke had “the gift”).

So here’s to “The Dude”, who went from rags, to riches, to even more riches, back to rags and finally to jail… and here’s hoping he can make it all the way back some day.

If you’d like to help Lenny get out of jail (he can’t afford his $500,000 bail) please donate here:

featured image courtesy of:
“nails” image courtesy of:
lenny and wife image courtesy of: Frederick M. Brown/Getty Images
jail image courtesy of:

Martin Stezano

About Martin Stezano

Uruguayan born and American raised with a unique perspective on the domestic and international sports scenes. It will both tickle your funny bone and enlighten your mind. Love it or hate it...just read it.