We all know that professional athletes earn a substantial amount of money over the course of their careers through player contracts and endorsements during their careers (and some after their careers, I.E. Michael Jordan). Unfortunately, not all athletes are able to maintain their financial stability for long after retirement because they are plagued with terrible business sense.

A large number of athletes have proven that bad investments and questionable business ideas are in store for a high percentage of athletes including some you would think could never make this list with the amount of money they made through their careers.

With that said, we decided to create a list of the top 20 athletes with terrible business sense with hopes that current rich/famous athletes can read it and learn from their predecessors business, investment and life mistakes.

It was fairly difficult to keep this list at 20 and to not add athletes who simply had awful money management or drug problems, but we tried to keep the list as business related as possible. The list is based on total amount of money lost, terrible business ideas/ventures, terrible business investments and in some cases just so crazy it had to be mentioned.

20. Mike Pelfrey

Ken Blaze-USA TODAY Sports

Ken Blaze-USA TODAY Sports

Former first-round draft pick for the Mets in 2005, Mike Pelfrey made one extremely bad business investment that would result with nearly all of his assets being frozen in what has become legendary ponzi scheme.

Robert Allen Stanford and his $8 billion ponzi scheme left Pelfrey one of the multiple baseball player victims significantly impacted from bad investments. At least he wasn’t the only athlete to fall victim here, he was just the only of the few that tied up an admitted 99% of his assets with the company.

19. Marion Jones

via smh.com

via smh.com

Marion Jones was a three time Olympic running gold medalist and was primed to continue making history until she was caught for steroids and began her life of crime as a back up business plan.

On top of being dishonest about using steroids, she stayed busy with various illegal business endeavors ranging from check counterfeiting to money laundering to illegal drugs.

She was indicted in 2008 and went from one of the fastest women in the world to losing her gold medals, filing bankruptcy and ended up in jail for six months.

18. Deuce McAllister

via buffalobills.com

via buffalobills.com

Former two time Pro Bowler and Saints running back thought he could transition well from the football life to the car dealership owner life and ended up on his backside.

After making around $70 million over the course of his football career McAllister could not afford to keep his car dealership afloat resulting in bankruptcy and a serious lawsuit in which Nissan wants well over $6 million from him.

17. Raghib “Rocket” Ismail

via nbcprofootballtalk.com

via nbcprofootballtalk.com

With all the random business ventures that Ismail attempted to invest in you would think that at least one would pan out right? No football does not count in this case.

After an awesome NFL career with many memorable moments he decided to try his hand at multiple businesses including a record label called COZ Records, a Rock N Roll Cafe, a movie, a strange national phone card dispenser plan (hmmm….), calligraphy and who could forget the most awesome business ever……cosmetics?

Estimated $20 million earnings – Estimated $18 million lost to failed businesses.

16. John Elway

REUTERS/Rick Wilking

REUTERS/Rick Wilking

Although John Elway is far better off than most athletes (or all) on this list, he has had his fair share of bad business ideas that have led to more lost money than some of the athletes on this list made in their careers.

John Elway decided to invest $15 million into Mueller Capital Investment which turned out to be a ponzi scheme worth over $70 million.

However, Elway did make a great business decision when he decided to sell all of his car dealerships which made him more money than most NFL players earn over a lifetime.

If only Deuce McAllister had thought of that….

15. Sheryl Swoopes

via apbspeakers.com

via apbspeakers.com

After being the face of the WNBA and signing a deal with Nike for her new “Air Swoopes” show brand she still somehow managed to file bankruptcy back in 2004 and blamed it on her agents accusing them of mismanagement.

After making an estimated $50 million or so over her career, she somehow went bankrupt for owing close to 3/4 of a million dollars.

Sounds to me like a number of bad business and/or financial decisions to me…..

14. John Daly

AP Photo/The Commercial Appeal, Jim Weber

AP Photo/The Commercial Appeal, Jim Weber

John Daly is a former two time PGA champion attempted to make a career out of gambling with his extensive earnings from his golf career.

Apparently it did not go as planned and rather than increasing his investments, it resulted in him losing around $60 million according to his autobiography.

Although, he must have broken some kind of record for famously (or infamously) losing over $1 million only two and a half hours and over $1.5 million on a separate occasion.

13. Diego Maradona

via fansshare.com

via fansshare.com

At his prime Marradona was in the discussion for the best soccer player ever. At his low point he had problems with cocaine and taxes resulting in over a year away from soccer and a hefty $26 million owed to Italy in back taxes (plus interest and penalties of course!).

Taxes should not be a problem for someone who is in the discussion for the greatest soccer player ever, but he is not the only athlete to not understand that they actually have to pay their taxes too.

12. Johnny Unitas

via nbcsandiego.com

via nbcsandiego.com

Unitas had an absolutely amazing NFL career resulting in three MVP awards, a Super Bowl and 10 Pro Bowls. He is in the NFL Hall of Fame and will forever be known as one of the greatest quarterbacks.

However, he along with many other athletes had terrible business sense which was eventually his true downfall in life.

Bowling alleys, real estate, a restaurant air freight business and finally a circuit board manufacturing business all failed or tanked and Unitas had to file bankruptcy. So did his wife.

Even at the time of his death he had a lawsuit pending that was sure to impact his remaining businesses.

11. Archie Griffin

via sportsonearth.com

via sportsonearth.com

Is he too close to number one on the list? Maybe, but I selected his place based on two points: he failed in his NFL career and he failed in his attempted shoe business(s).

After what is arguably the best college football career in history he failed miserably at the NFL level and pretty much did the same with his shoe business outside of his career.

I wonder if he sold more shoes than he had yards in his NFL career?

10. Scottie Pippen

via thenypost.com

via thenypost.com

Scottie Pippen had a stellar NBA career compiling six NBA Championships and seven All-Star game appearances with an All-Star MVP award.

He also should have had at least one Defensive Player of the Year Award as well. (Just saying)

However, he was not the best off the court and ended up being another athlete with terrible business sense. Luckily, his money loss was strictly business without any illegal business endeavors. It came from bad investments in real estate and incredibly poor financial planning.

Did I mention the private jet he decided to purchase which he was being sued for and when he allegedly could not afford the payments for his jet lawsuit he attempted to make an NBA comeback in order to afford to pay his lawyers.

9. Mark Brunell

via nfl.com

via nfl.com

Mark Brunell had an excellent college football career winning two straight Rose Bowls for the University of Washington and had an above average NFL career for the Jaguars which included a couple of playoff appearances, including a trip to the AFC Championship.

Brunell decided to take his chance with real estate and invested in numerous business ventures that played a significant role in his bankruptcy.

8. Dick “Night Train” Lane

via nfl.com

via nfl.com

The “Night Train” had an illustrious NFL career and became known as one of the hardest hitting players in the NFL on his way to the Hall of Fame. He struck fear in the hearts of offenses everywhere.

Unfortunately, there were multiple business bumps in his road of life that resulted in bad business investments in real estate, music and a number of scams that left him broke.

7. Derrick Coleman

via edgecastcdn.com

via edgecastcdn.com

Derrick Coleman had an excellent NBA career and was able to be a factor for over 14 seasons.

Unfortunately he was really bad at making solid business investments, but he had a really big heart and decided to invest in real estate and business endeavors to help his city, Detroit.

The result was bankruptcy court where he owed over three times what he ad left. After amassing nearly $90 million in his NBA career, he filed bankruptcy with claimed assets of just $1 million while he owed over $4 million.

6. Vin Baker

via theseattlesalmon.com

via theseattlesalmon.com

Vin Baker had a great NBA career earning over $90 million in 13 years.

Unfortunately three things happened to Baker; alcohol, gambling and bad investments.

If alcohol and gambling was not enough, Baker attempted to own multiple restaurants or Fish Houses that failed and resulted in him attempting a comeback at….Starbucks?

He is certainly optimistic, happy and seems to have learned some valuable life lessons which I can certainly respect.

5. Travis Henry

via suntimes.com

via suntimes.com

I am not sure why we did not put him at the top of the list based on his foolish decisions but he is here and let me tell you why.

He has been indicted on drug trafficking charges (cocaine) and has been put in jail before because he cannot afford to pay child support.

Not only did he make the poor decisions when he decided to have nine children with nine different women, but he decided to try drug trafficking instead of the business he had been working for his entire life, football.

Thanks to his drug trafficking indictment, Henry lost out on an NFL contract rumored at around $25 million with the Denver Broncos. Terrible business sense…

4. Latrell Sprewell

via bleacherreport.com

via bleacherreport.com

Sprewell could have had an awesome NBA career and at one point I have to admit I was a fan of his game.

However, he has fallen far, far from grace with his on-court and off-court antics along with his many failed business ideas and absolutely astounding NBA contract refusal.

First he choked and allegedly punched his head coach, second he invested in a silly car rims company (plus more I am sure) and finally he turned down a three year NBA contract worth $21 million and claimed it was not enough money to feed his kids.

Awful ending to what could have been a bright career.

3. Michael Vick

Steve Mitchell-USA TODAY Sports

Steve Mitchell-USA TODAY Sports

Michael Vick could have easily made number one on the list just based off the sentence above.

He was a phenomenal NFL player who helped revolutionize the quarterback position and my friends used in the Madden football game to win every time (because they ran every time!).

Anyhow, he went from superstar in the NFL to dog fighting.

That is one of the absolute dumbest business (and moral) decisions I have seen in my life and it definitely ruined his reputation and career.

He has made a valiant effort to make amends and has even landed another contract in the NFL with the Pittsburgh Steelers. Still, those decisions still have to be haunting him to this day.

2. Lenny Dykstra

via nbcwashington.com

via nbcwashington.com

After a stellar career in professional baseball Dykstra attempted multiple business ventures including a high end magazine company, real estate, stock trading, car washes and private jet company that eventually helped seal the deal.

He was able to earn nearly $70 million, lose it all and get charged with fraud and theft.

Seriously failed businessman….

1. Mike Tyson

via bet.com

via bet.com

Mike Tyson had a star studded boxing career until the crazy decision making started taking over. Rape, domestic violence, drugs, DUI, the ear incident and don’t forget the Bengal tigers, cars, houses, etc.

Did I mention Bengal tigers? Bad business investment….

Anyhow, this man somehow blew away nearly $400 million worth of money in a relatively short time through incredibly terrible life and business decisions.

With that much money lost, he has to be number one on a lot of “not so good” lists.

Please don’t beat me up Mike….the list had to be made sir.

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