How Seven Broke Athletes Burned Through Mountains of Cash

We all know that athletes make eye-popping money these days, but star athletes turn into broke athletes with shocking regularity and speed. Even role players earning minimum contracts should be doing well enough that they never have to work again after retirement. And yet, despite the whopping salaries, according to a 2015 Money Magazine profile of Allen Iverson (spoiler), a staggering 60% of NBA retirees are broke within five years of their retirement.

So why do we see so many athletes go broke? We looked at some of the most famously broke athletes to see if we could find some common threads. A few quick amateur financial tips from my investigation: don’t buy 12 cars for one person; don’t buy more houses than you can live in or visit in a year; don’t get divorced; and definitely don’t drop $1.5 million on a slot machine.

Joe Smith

No, I’m not making up the first entry and giving it the least creative name possible. Joe Smith was the first overall pick in the 1995 NBA draft and played for 12 teams during his 16-year NBA career, earning over $61 million in salary. In 2018, Smith was the first player featured in Alex Rodriguez’ CNBC show “Back in the Game,” a show that featured Rodriguez giving financial advice to broke former athletes. In a related story, the New York Yankees began auditioning financial analysts from Goldman Sachs to play third base.

Smith took home over $18 million after expenses, taxes and fees, and yet was living paycheck to paycheck when he appeared on the show, relying on limited income from basketball lessons while sinking further into debt. As Smith told it, his fortune was spent on houses in every NBA city he played in, and this is a guy who played for 12 NBA teams, as well as a huge car collection. Smith would make a number of bad investments and go through a costly divorce. Ultimately, the player who never earned less than $1.8 million in a season needed the money management brilliance of Alex Rodriguez to tell him he had to start spending less than he was earning. Smith comes across on the show like a genuine guy who made some bad decisions, he’s a broke athlete we (hopefully) can root for.

31 points, 21 rebounds, 7 blocks, 4 steals 🤯🤯@JoeBeast95 was the National Player of the Year in 1995.
He showed why on this day, 25 years ago.

➡️https://t.co/VXnQhXO0xu pic.twitter.com/2vdtoyIpy1

— Maryland Men’s Basketball (@TerrapinHoops) March 18, 2020

Lenny Dykstra

We’ve covered Lenny “Nails” Dykstra and his downward spiral here once or twice before, he’s one of our crazier broke athletes. Regular listeners to the Howard Stern show will also be familiar with the batty, washed-up former outfielder’s increasingly crazy rants on calls to the show over the years. In his time, Dykstra was a good, well-paid outfielder, who as recently as 2008 listed his net worth at over $58 million. Dykstra was involved in numerous businesses and was raking in endorsement money.

Dykstra purchased an $18.5 million mansion in California from Wayne Gretzky in 2007. He started his own investment magazine, “Nails Investments,” despite knowing nothing about investments or running magazines. He gave financial advice in a regular online column for a major website, because responsibility means nothing in that business. The entire time, and since his playing days, Dykstra was addicted to cocktails of painkillers, alcohol and narcotics. In a 2009 bankruptcy filing, Dykstra would tell the government that his true net worth was negative-$31 million, and that he had only $50,000 in assets. He would immediately sell over $400,000 worth of assets after the filing. He would be indicted and convicted on several counts of bankruptcy fraud and money laundering. This is the type of financial management only “Nails Investments” can provide.

We’ve detailed Dykstra’s downward spiral and list of arrests and convictions in both of those linked columns. It would be impressive if it weren’t tragic.

Here is documented proof #RonDarling faked cancer @MLB @METS @nypost @nytimes @NYDailyNews @SNYtv @MacmillanUSA #robmanfred #rondarling #garycohen @FOXSports @MLB_PLAYERS https://t.co/ZvvSxtgfga

— Lenny Dykstra (@LennyDykstra) June 22, 2020

Then again, screw Lenny Dykstra, I’m glad he’s a broke athlete.

Antoine Walker

Former NBA Champion, three-time All-Star and NCAA Champion Antoine Walker was the dad-bodied basketball hero of chuckers everywhere. Walker never met a 3 he didn’t expect to make, despite a 32.5% career shooting percentage from beyond the arc. Walker would earn more than $108 million in his NBA career, yet might be most famous for being a broke athlete.

Walker made some insane decisions with his money. During his career he would allegedly only wear designer suits, and never the same one twice. He owned a dealership worth of cars, including two Bentleys, a Hummer, an Escalade, a Range Rover and two Mercedes. In a 2010 bankruptcy filing, Walker claimed that he was also supporting more than 70 friends and family members, an all-too-familiar story of athletes not being able to say no to hangers-on. Prior to the filing Walker had been arrested in Las Vegas in 2009 for writing bad checks to 10 casinos for a total of more than $1 million, so don’t feel too bad for him.

Walker’s saga as a broke athlete was captured in a documentary that I see first mentioned in 2014, was coming soon in 2018, and appears to be on the verge of release in 2020, according to IMDB.

Watch “Gone In An Instant // Official Trailer” by @WalkerAntoine8 on #Vimeo https://t.co/P5pFJAkK7M

— Antoine Walker (@WalkerAntoine8) June 4, 2018

John Daly

Two-time major champion (PGA Championship ’91, British Open ’95) John Daly has some personal demons. The golfer has famously battled alcohol as well as weight through his career, but by far his biggest issue seems to be gambling. In his 2006 autobiography, Daly revealed that he has lost what he estimated to be between $50 and $60 million gambling. According to his own account this included over $1.5 million in October 2005 alone, on a single slot machine, at the Wynn Casino in Las Vegas. At $5,000 a spin that only amounts to 300 spins, but dropping that much money into an openly rigged game like a slot machine is maybe the worst gambling decision I’ve ever heard of.

With a current net worth of around $2 million it’s actually a stretch to call Daly a broke athlete, but he more than qualifies for burning through mountains of cash. In 2014 Daly told TMZ that he would often have “more than $600,000 on the table … I would play seven hands at a time.” When they asked if he regretted his millions in losses, Daly responded “Man, I had a great time.”

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Allen Iverson

Allen Iverson is a broke athlete with something to look forward to. In 2030 Iverson will be able to access a $30 million “rainy day fund” that was set up for him by Reebok as part of his lifetime endorsement deal. Iverson, an 11-time NBA All-Star who earned over $150 million in his career, famously burned through his fortune by spending. According to 2012 divorce filings, Iverson lived a lifestyle that included never carrying luggage on the road, instead simply buying new clothes every time he landed in a new city. His monthly spending was at one point estimated to be around $380,000, including payments on multiple multi-million dollar mansions, exotic cars, jewelry, and supporting more than 50 friends and relatives. Iverson added a gambling issue to that, reportedly dropping more than $1 million in one night in Atlantic City, and has allegedly been banned from casinos in both A.C. and Detroit.

At his bottom, during a 2012 divorce proceeding, Iverson reportedly pulled out his empty pants pockets and shouted to his ex-wife Tawanna that he didn’t “even have money for a cheeseburger!” Tawanna then supposedly handed him $61 in cash in what reads as generosity, but may have been ice cold sarcasm. A.I., if you’re reading this through some miracle of the internet, we’d be happy to buy you a burger and talk hoops any time.

He’s selling socks now if you want to pitch in.

If you haven't grabbed a pair of my new @stancehoops socks get them today. Link in my bio… https://t.co/iKWupL8rrh

— Allen Iverson (@alleniverson) August 10, 2016

Mike Tyson and Evander Holyfield

No wonder these two are talking about fighting one another for a third time despite both being well into their 50s and long retired from boxing. Holyfield earned over $230 million over his boxing career, but he was a broke athlete before he was even able to retire. Holyfield would famously lose immense amounts of money to a high-end lifestyle, gambling in Las Vegas and, primarily, to fathering 11 children with five different women. No judgments, that’s just expensive.

Tyson spent more lavishly than Holyfield, at one point claiming a $400,000 per month minimum. In addition to racking up a $13 million back-tax bill, Tyson was just careless with money. I don’t only mean that he spent unwisely – he did – but he also at one point claimed to have just flat-out misplaced a suitcase with $1 million cash in it. Which I think we can all identify with. Tyson loses a million dollars like I lose the remote. I wonder if he checked in the freezer.

Tyson would famously spend millions more on totally normal purchases like gold chains lined with 80 carats in diamonds, limousines and a live Siberian tiger. Yeah, turns out that wasn’t a joke in The Hangover, Tyson really did own a tiger. As far as I’m aware only one of them has bitten a human, spoiler if you haven’t seen this clip, it’s not the one you’d expect.

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