10 Dumbest Athletes (When It Comes to Money) + Lessons From Each Story

I am discussing athletes who were once at the top, top of their field, top of the world, making millions of dollars, living a lifestyle that any one of us would easily envy, but through poor decisions and financial choices and personal choices, they lost a lot of money, and in some cases all their money.

This athletes are ranked by my estimate of who lost the least to who lost the most as a percentage of net worth, so the stories are going to get increasingly worse and worse.  And of course, this article is purely for entertainment, and no one knows these athletes’ true net worth unless they’ve personally disclosed it.

Now, listen up, because these numbers are gonna be so big, they won’t even seem real, but of course there is a lesson to be learned from each one.

1. Tonya Harding

Olympic figure skater Tonya Harding, who compared to others on this list didn’t lose all that much money given that everything fell apart before she could even reach the peak of her career.

If you know the story, you know that Harding’s ex-husband, Jeff Gillooly, hired a hitman to break Harding’s competitor and reigning U.S. Figure Skating Champion, Nancy Kerrigan’s right knee.  And on January 6, 1994, one day before the U.S. Figure Skating Championship first Ladies’ Single competition, the hitman attacked Nancy Kerrigan, swinging a twenty-one-inch ASP telescopic baton at her right leg, and although he didn’t break her knee, Kerrigan’s leg was severely bruised and she was not able to compete, and Tonya Harding won the U.S. Figure Skating Championship two days later.

There wasn’t enough evidence to implicate Harding for criminal charges of being involved in the planning and execution of this attack, but evidence came out clear enough to implicate her in the cover-up and she pleaded guilty to conspiracy to hinder prosecution, she was slapped with probation and a six-figure fine.

However, the United States Figure Skating Association met later that year and concluded that Harding did have prior knowledge of the attack and was involved prior to the incident, of course their standards for evidence are lower than criminal standards, but as a result of their investigation, the Association stripped Harding of her 1994 U.S. championship and banned her for life from participating in United States Figure Skating Association events either as a skater or a coach.

So at twenty-three years old, Tonya Harding lost her income from skating as well as sponsorship opportunities, she went on to earn the majority of her income from paid interviews–at first charging up to $600,000 dollars. But that eventually ran out of steam, and Harding ventured into boxing, acting, and even lowkey jobs like landscaping and house painting.

Most recently, Harding earned a minimum of $125,000 dollars to Dance with the Stars.  So apart from perhaps some early income from speaking gigs and the one-off opportunities like Dancing With the Stars, Tonya Harding’s net worth is probably quite average these days at least compared to the multi-million, possibly even eight-figure net worth of other skaters who enjoyed long careers and fame in the profession.

Key Takeaways

So what are the takeaways here from Harding’s sad story?  Number one, don’t marry an idiot and number two, always have a backup plan, if your job or your business fail, do you have something else lined up you can do to make money?

Better yet, do you have multiple streams of income to get you through those tough times?

If you want to learn more about my personal approach to personal finance, be sure to check out my Prosper course.

2. Dan Marino

What happened to Dan Marino is basically what happens today when people go all in on a stock and worse than that, all in on a stock they don’t know much about.

The former Miami Dolphins Quarterback invested a hefty amount into a Hollywood visual effects company called “Digital Domain,” which, on paper, looked really good because of their really cool work in Titanic, Transformers and other high-budget films. When the company made a hologram of the late rapper Tupac Shakur at Coachella in 2012, Marino was so impressed that he put in $14.5 million dollars of his hard-earned money into the stock at its peak price. But a year later, it completely tanked, and Marino lost $13.6 million of his initial investment.

However, Marino is still in good financial shape as of today and is estimated to be worth around $35 million dollars. But again, assuming he started with a net worth of say $50 million, a 30% decrease is still a big loss, even to a multimillionaire.

Key Takeaways

Marino’s story is a good reminder that we should never be too confident about one company and, for the love of all things investing, diversify your portfolio.

3. Dorothy Hamill

Dorothy Hamill, another famed ice skater.  The Olympic gold medalist was skating and minding her own business when, of course, her now ex-husband convinced her to invest millions into what was basically a traveling ice skating circus. When that “surprisingly” went bankrupt, she went bankrupt as well.

In 1996, it was revealed she was $1.6 million dollars in debt. But Hamill seems to have learned her lesson.

In 2018, Hamil told CNBC, “The good news is I’ve finally found people that are trustworthy… As an athlete you don’t learn all these things. You’re just focused on training.”

As of today, her net worth is estimated to be a comfortable $5 million dollars, and again, this is on celebritynetworth.com, which I don’t think has any real knowledge of celebrities’ net worth, but it sounds reasonable.

Key Takeaways

It is that you should not trust the “money matters” in your relationship to someone else, be it your spouse or your partner, you need to learn this stuff yourself, there are too many people in relationships where the other spouse handle the money stuff, no, everybody needs to become financially literate on their own and learn about saving and budgeting and investing.

4. Michael Vick

Shortly after signing a 10-year, $130 million dollar contract with the Philadelphia Eagles, the former NFL quarterback’s career turned upside down when his dog fighting scandal broke loose and angered the whole nation.

Because in America, let’s face it: as beloved as football is, dogs are more so. Vick ended up in prison and lost two seasons’ worth of that sweet NFL money, and when he finally came back to playing full-time, he was getting paid at way lower rates.

Before the scandal, Vick made almost $60 million dollars in the NFL. As of 2021, that net worth dropped 73% to an estimated $16 million dollars.

But it appears Vick has learned his lesson, and has since then become an animal rights advocate.

Key Takeaways

The money lesson is really simple here, and it’s simply don’t engage in illegal activities at the peak of your career, or right before signing a $2 million dollar endorsement deal with Nike.

If you ever come into money and have any hobbies that seem even the tiniest bit illegal, re-think it.

However, I applaud Michael Vick for recognizing his mistakes and moving forward gracefully.

5. Evander Holyfield

Possibly one of the most notable names in boxing, Evander Holyfield was at the top of his game in the 80s and 90s. According to the BBC, which is surely a more accurate source than celebritynetworths.com, Holyfield once had a net worth of $230 million dollars.

And by the way, even though Mike Tyson famously bit Holyfield’s ears at the MGM Grand in 1997, Holyfield still earned $35 million dollars from that fight alone.

But with great money comes great responsibility, and soon Holyfield, like most regular people, got swept up in child support and the 2008 housing crisis.

Holyfield bought a mansion that reportedly cost him at least $1 million dollars per year to upkeep, and in 2008 he ended up selling it for a fraction of what he bought it for. Additionally, Holyfield had 11 mouths to feed, 5 baby mamas to deal with, and by the time he was reported to be broke in 2012, he owed half a million dollars in child support and maintenance.

As of 2021, he’s estimated to have around $1 million dollars left. That’s a staggering 99.5% loss from his original earnings.

But things seem to be looking up for the boxing legend. Holyfield told BBC Sport in 2015, “I made $230 million in the first half, so I’ve still got reasons to live.”

Key Takeaways

There are lots of lessons to be learned from Holyfield’s story, but one big one is this: don’t buy too much house.  Just because you can qualify for a mortgage on a $300 thousand dollar home, on a $700 thousand dollar home, on a $1.1 million dollar home doesn’t mean you should buy a home that expensive.

As with everything, with housing live below your means so you can build your emergency fund, pay off debt, and invest as much as possible.

6. O.J. Simpson

Once upon a time –certainly before 1994 – former star NFL running back O.J. Simpson had $10 million U.S. dollars in the bank, which is equivalent to around $18 million dollars today.

Then, it all changed when he may or may not have done something to lose it all.  As I’m sure all of you know, in 1994, O.J. was arrested and charged with the murders of Nicole Simpson Brown and Ron Goldman.  Although he was acquitted of the criminal charges, the civil suit became a financial nightmare as O.J. as in February 1997 a civil jury in Santa Monica found unanimously found the former football great liable for the wrongful death of Ron Goldman.

Simpson was ordered to pay a whopping $33.5 million dollars to the Goldman family as a wrongful death settlement, which is reported to be worth $70 million dollars as of today due to interest. After additional high-profile run-ins with the law, O.J.’s once-robust bank account has completely tanked… somewhat.

According to Money.com, O.J.’s net worth today could land between $250 to $3 million dollars, which is obviously a fraction of what an NFL Hall of Famer decades after retirement could have been worth with sound financially decisions.  However, take this relatively low net worth figure with a grain of salt since legend has it that O.J. owns off-shore accounts that could be worth millions more.

Key Takeaways

What’s the lesson here? Don’t get yourself involved in a high-profile murder case.

7. Mike Tyson

Another boxer with legendary status is Mike Tyson.  From winning streaks  to raising tigers and driving exotic cars, Iron Mike had it all – including a taste of Holyfield.

It’s estimated that Tyson earned a combined $400 million dollars throughout his career, which according to Forbes, is worth $685 million dollars today. But after an unfortunate series of arrests, personal problems and lavish spending, he lost most of it.

In 2003, Tyson filed for bankruptcy and it was revealed that he was $23 million dollars in debt.

By 2005 he retired and went straight to Hollywood and as of now, Mike seems to be in good shape and has been in comeback mode.

According to Celebrity Net Worth, Tyson is worth $10 million today.

Key Takeaways

So the lesson from Mike Tyson’s story is that even when things look darkest, it is still possible to turn your financial life around and end well.

8. Mark Brunell

If you think you spend too much money on takeout, imagine losing millions because of a fast-food chain.

Mark Brunell made his mark on the NFL by becoming a three-time Pro Bowler. Over his 18-year NFL career, it’s estimated that Brunell made over $70 million dollars, and had a peak net worth of $50 million.

But after a few – ok, many – bad investments, like losing millions on real estate and failed business ventures, Brunnel was barely keeping up. He filed for bankruptcy while still playing in the NFL, and to make it worse, the icing on the cake was a $9 million dollar loss from Texas burger chain Whataburger.

Key Takeaways

So here’s a lesson for you from Brunnell’s story: If you have a demanding career, consider just putting your money into plain old-fashioned index funds; you’re busy enough with your career and probably don’t have all that much time to truly research and vet one-off investments, so strongly consider just investing your money the passive way and watching it grow over time, and if you don’t know what an index fund is, be sure to watch my investing for beginners video.

9. Curt Schilling

Schilling’s story could send chills down any professional athlete’s spine. After 20 years of a successful career in Major League Baseball, Schilling decided to go all in on a top American pastime: video games.

Before he retired, he invested $50 million dollars to create his own video game company, 38 Studios, which he believed would be the best video company of all time. A couple years later, the company went under and Schilling lost all of his $115 million dollar fortune.

As of today, it’s estimated that his net worth is in the low seven figures.

Key Takeaways

There are a couple, first one is specifically for those of you considering starting a business or who already have a business — don’t put all your eggs in your business.  I can’t tell you how many business owners I’ve seen as a CPA who’s only real asset is their business, and like any business owner, like any entrepreneur, you have to be optimistic about your business and want it to grow and have a vision of massive success down the line, maybe even a large exit or something like that, but think about it.  Your business could fail, and essentially having all of your net worth wrapped up in your business is just like having all of your net worth tied up in a single stock, sure you have more control over this asset, but the lessons I mentioned previously about diversifying your portfolio apply here as well.

And thankfully, the IRS actually has some pretty significant tax advantages for business owners who invest some of their business profits into other assets through accounts like SEP IRAs and Solo 401(k)s.

Also, lesson number two, just because you really enjoy doing something doesn’t necessarily mean it’s going to transfer into a successful business model.  I’m not saying it can’t, but consider yourself lucky if you find yourself with a successful business pertaining to something fun, like video games because more often than not, and we see this with a lot of people who start YouTube channels, betting on video games for all that you have doesn’t always work out in your favor.  Unless you’re PewDiePie.

10. Lenny Dykstra

This list wouldn’t be complete without  Lenny Dykstra, who takes the cake by reportedly having a net worth of negative $25 million dollars, of course that’s according to celebritynetworth.com, which may or may not be completely accurate, but whatever Dykstra’s net worth is, I think we can all agree it’s pretty low.

So what’s Lenny’s story? Well, known as “Nails” in the baseball world, Dykstra made a name for himself by playing with reckless abandon, which foreshadowed his future finance situation. This three-time All Star and one-time World Series champ is as financially troubled as athletes go. It all started with a DUI, which turned into drug use, which turned into a domino effect of legal issues.

Dykstra eventually retired from baseball at the age of 33, and then came the Players’ Club, Dykstra’s business venture that was basically an all-in-one private jet rental, magazine, and financial service for retired professional athletes.

Sounds legit, I know. To nobody’s surprise, the whole thing failed and soon Dykstra found himself in classic legal trouble like fraud and good ol’ grand theft auto.  Throughout the years Dykstra had other business endeavors as well to try to make up for his financial troubles, I remember as a kid growing up in the Inland Empire, which is an area east of Los Angeles here in Southern California, my dad and I would go to.

In 2008, Dykstra had an estimated $58 million dollars in the bank, but filed for bankruptcy the following year, listing less than $50,000 in assets.  I think the lesson we can learn here is that one bad decision can snowball into a lifetime of pain, it all started with Lenny’s stupid decision to drive while under the influencers, and if you do that, you should go to hell, you really should, there was never an excuse for drunk driving and especially not these days when in minutes you can pull out your phone and call a Lyft, so you don’t end up like Lenny Dykstra.

Key Takeaways

Bottom line, folks: don’t make dumb decisions, don’t break the law, be smart about who you get investing knowledge from, and diversify your portfolio.