I bet you thought I had given up on my dream of becoming The Next Great American Blogger(TM)! How mistaken you are! I had been distracted by the rootin’, tootin’, cowboy-shooting majesty of Red Dead Redemption 2 and, in great news for all of you, I have done it. I shot all the cowboys and all the animals, and tamed the West so it can be inhabited by people who invented gluten allergies and the concept of casting couches.
Today’s subject is one most of you are probably familiar with, but also one in which you only have pieces of knowledge regarding this human stampede. Lenny Dykstra was a baseball player for the World Series winning 1986 New York Mets and established his Hall of Fame career as a Philadelphia Phillile. He was also so much more than this as you will certainly see.
Dykstra was a thirteenth round pick in 1981 Draft where a GM noted he was “perfectly designed emotionally” to play baseball because he had “no concept of failure.” English majors would call this “foreshadowing.” He followed up this draft position – again, in the thirteenth round – by demanding to be paid like the first overall pick as he saw himself as the best player in the draft. He did not get his payday, but managed to ingratiate himself with his team one night at a restaurant when he picked his leg up and farted on a table full of priests. He picked up the nickname Nails for being a hard nosed blue-collar player constantly with a lip full of chew, and was acquired by the Phillies for this reason. He had a mostly injury-stricken run early with in Philadelphia after suffering broken ribs and a broken collarbone after crashing his car drunk and then immediately running full speed into a wall like a Looney Tunes character immediately upon his return. Once he managed to stop destroying himself, he ended up finishing second in the 1993 MVP race after accruing a league-leading walks. He would later say his spike in walks was due to paying a team of private investigators to dig up dirt on umpires as blackmail for a more favorable strike zone. Dykstra is the personification of “unchill.”
His first non-baseball side hustle was a car wash in Simi Valley, CA for which he was later sued by a partner who alleged Dykstra had been using steroids almost his entire playing career and frequently bet on his teams while he was playing (I don’t know how this was all suppose to fit over a contract dispute for a car wash either). If you don’t follow sports that closely, gambling is basically the worst thing you can do – an NFL linebacker was arrested for beating the shit out of his girlfriend and was cut only to be signed within 36 hours by another team, but gambling ruins the INTEGRITY of the game! Cheating, performance-enhancing drugs, fighting, domestic abuse, abandoning children – all fine, but don’t you dare gamble! /clutches pearls, fans self dramatically. He was also arrested for criminal sexual harassment of a 17-year old, because let’s throw that on top of the pile.
He began managing a stock portfolio and had the idea of businesses that strictly sold their items on eBay, like Catherine Keener’s character in “40 Year Old Virgin” where a confused Jonah Hill tries to buy the disco heels with the fish inside. It didn’t pan out, but Jim Cramer had him flaunt his stock-picking “skills” on “Mad Money”. So many people assumed Jim Cramer was NOT a huge dumb ass, but man, history has not treated him kindly.
He famously purchased super-hottie Paulina Gretzky’s dad’s house (you may know him as hockey legend Wayne Gretzky) in an attempt to flip it. This did not pan out. He bought the home for $17 million dollars, ended up owing $13 million on it, at which point the bank stationed security guards at the property after they discovered he starting stripping the house of any items that could be resold (appliances, toilets, counter tops, flooring) and that he had let the house fall into such disrepair it had become uninhabitable due to extensive water damage and toxic molds. A second unrelated property owned by Dykstra was found littered with empty beer bottles, trash, dog shit and other “unmentionables”. I dare you think of what could be considered “unmentionable” after that preceding list. About this time, a porn star publicly accused him of writing a worthless check for her “services.” Lenny Dykstra – the guy that tried to pay a prostitute with a check. (Disillusioned Dilettante interjection: so did Jerry Springer while on Cincinnati City Council!)
In 2008, Dykstra had the worst possible idea at the worst possible time – he was going to create a magazine marketed specifically to professional athletes about financial advice. Magazines! Specifically for professional athletes! About financial advice! In 2008! This was a bad idea made worse when he elected to throw a $600,000 launch party for the magazine. Shockingly, an expensive and in-poor-taste party was attended by one future-President Trump. One of his writers documented his brief time there and noted incidents of blatant credit card fraud, bounced checks, openly racist, homosexual and misogynist comments (Dykstra responded to these claims with, “nobody can call me a racist – I put three darkies and a bitch on my first four covers.” I don’t know about you guys, but I’m convinced!), and failure to pay rent on his Park Avenue office (leasing property on Park Avenue precludes you from ever providing financial advice to anyone ever). ESPN estimated he was named in AT LEAST twenty-four legal actions in 2007. Before long, he was living in his car and loitering in hotel lobbies until they threw him out. In 2008, he declared bankruptcy, claiming only $50,000 in assets against $31 million in liabilities.
In 2011, Dykstra was accused of sexually harassing another guest of a Fox Business segment off-air; when asked about the incident, he denied any knowledge by stating, “she’s just one of many, dude. She got to get on the space shuttle.” Remember that bankruptcy from before? He was sentenced to house arrest after pleading guilty to bankruptcy fraud after hiding and trying to sell assets, all while lying under oath. All that shit he has stripped from Gretzky’s house? Yeah he was busted trying to flip those for cash after failing to include them in the bankruptcy. He was permitted to go to work (“work” seems like a stretch based on the above information) or church (HA). During his house arrest, his housekeeper accused him of sexual assault. He was almost immediately arrested again during his house arrest and charged with drug possession (cocaine, ecstasy, and human growth hormone), identity theft, money laundering, indecent exposure, grand theft auto, and filing of false financial statements. A word of advice – if you are under house arrest, do not whip your dick out in public while doing a dozen other illegal things. He was held in jail at this point as he was unable to post bail, and eventually ended up requiring a public defender as he was facing 80 years (EIGHTY YEARS) in prison for financial fraud. At the risk of appearing to throw shade on these facts that many people are subjected to daily, this is a reminder this man was a MVP-caliber baseball player for championship-winning teams with a $6 million dollar annual salary and promoted as an elite stock-picker. He eventually spent six months in prison followed by 500 hours of community service. It was during his prison time Dykstra claimed to have finished reading his first book.
He would eventually release a book (duh) which celebrated his sexual conquests, steroid usage, friendship with Charlie Sheen at the height of his own unrelated spiral from glory, and sexual conquests. Did I mention sexual conquests twice? Lenny wants you to know he FUCKED. He bragged on Howard Stern about how he originally thought God put him on Earth to play baseball, “but he actually put me on Earth to get women off.” Lenny, as a baseball star, only went for the finest of the fine – jk he would fuck literally anything. He explained he would send ballboys into the stands to find willing women that he would 1. use a tongue depressor to inspect their health, 2. bang it out, 3. return to the game. Never let anyone try to convince you baseball is a demanding sport. He was very proud of fucking anything as long as their mouth was clean – I’m no doctor, but that doesn’t seem like the best possible screening for STDs – and later said “the canvas has gotta be clean before I do my artwork.” After Howard Stern laughed at these absurd claims, Dykstra returned with two women to verify his claims.
The good news is Lenny has turned his life around. You’ve read these articles and lived in the world – of course he didn’t. He reportedly trashed a hotel room and stole all the sheets, pillowcases and towels in 2017, while still leaving all his clothes and a suitcase with a note to the maids to send to his home (when asked later about it, Dykstra replied, “I might have had ten women in the room, might have had 15, might have had 20. Actually the only thing I had in that room was my dick in my hand”). He was arrested for uttering terroristic threats in May of 2018 after holding a gun to an Uber driver’s head, at which point he was detained with a pocket full of cocaine (he would claim he was held hostage by the driver). I’m really struggling to find a moderately upbeat place to end this story – online sites that specialize in estimating net worth suggest he has a net worth of -$25 million. Wait wait – he’s a regular feature on the internet’s frat house, Barstool Sports, where podcasts call him and prank call him until he hangs up. No, no, we can do better. His son, Cutter, knocked up the girl who played Meadow Soprano. There we are – imagine the being the descendant of a man who murdered people as part of his role as a mob head, and that is the more sane grandfather.
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