For some reason the majority of athletes have no clue what to do or how to live after retirement which often results in their lives simply falling apart. The main reasons seem to be lack of financial understanding, planning and management, but it really stems from poor decision making by the athletes.
A recent report by Fortune.com has said that 16% of NFL players lose all of their earnings and file for bankruptcy within a 12-year period after retirement. The report cited the National Bureau of Economic Research in their study of how players lose their money so soon after retirement. The NBA is not much better.
When you get accustomed to a certain lifestyle and certain expenses, you can get away with it when you have millions of dollars of income. However, the adjustment to being more frugal with their money is hard for some athletes to make when that income disappears. There's a great video out there of Herm Edwards speaking to NFL Rookies the the NFLPA Inaugural event a few years ago, explaining how rookies should manage their finances and learn to control their spending habits. The advice was pretty simple; don't buy more than what you need and keep your luxury spending to a minimum.
Our list is compiled with athletes from multiple sports that have failed since retirement for various different reasons including investments, financial mismanagement, too many handouts, criminal activity, attempted murder and even alleged murder but the glove was too small (hint).
There is no way to fit every athlete who’s life fell apart after retiring on a 20 person list, but we would love to hear your thoughts on who made it and who we missed.
20 John Daly
Daly loved to hit long drives on the golf course, drink hard off the golf course and gamble like his life depended on it.
After having an excellent professional golf career and winning both the 1991 PGA and the 1995 British Open, his off the course problems led to multiple problems post retirement.
According to his autobiography, Daly lost $1.65 million in just five hours playing slot machines at a casino (which has to be some kind of record) and has lost an estimated amount of $50 million to $60 million to gambling alone.
19 Marion Jones
Jones is the only female athlete on our list and was the first female athlete to become a millionaire. Unfortunately, her life fell apart after retirement and she turned to criminal activity in order to fix her financial problems.
Since retiring she has been through multiple lengthy trials stemming from her use of PEDs and various counts of check fraud. Part of what made the cases draw out so long was her initial denial of all charges which resulted in much more lawyer fees, court fees and of course fines from fraud convictions.
18 Dennis Rodman
Like a few others that made the list, Rodman definitely started his eventual downfall while he was still playing professional basketball in the NBA.
During his career he would spend insane amounts of money on ridiculous things and attempt to stay in the spotlight. He may be the only player in NBA history to sit down at mid-court and refuse to play anymore in the middle of a game, kick a cameraman in the crotch for no reason and wear a wedding dress for fun during the playoffs.
Since retirement, Rodman has consistently blown his money and his life away at a rapid rate. Somehow he still makes headlines and his most recent post retirement idea was to become friends with Kim Jong-Un and he made four trips to North Korea to spend time with him. It is reported that Rodman even sang Jong-Un happy birthday.
17 Curt Schilling
Unlike some of the athletes on this list, Schilling’s life did not fall apart because of being irresponsible, acting foolish or wasting money on luxuries and friends/family.
Instead he decided to invest everything he had in his video game company called Green Monster Games which later became 38 Studios.
His idea sounded great, but it is apparent that he did not really know what he was doing which resulted in him losing over $50 million of his personal money along with another $75 million in taxpayer money.
16 Scottie Pippen
Pippen had an awesome Hall of Fame NBA career earning $120 million throughout his time in the NBA before he retired. Unfortunately for him, poor financial decisions led to his downfall post retirement.
He made a large number of terrible investments in real estate and other ventures that cost him dearly, yet he continued to try and make the unsuccessful somehow successful. It did not work.
To make things worse, Pippen decided to purchase his very own private jet so he could travel in style. That also did not work out as he overpaid for the jet ($4 million) and it would not work properly which made it dangerous to fly. Pippen ended up dropping another million just to get it running and has to be regretting it.
15 Antoine Walker
Walker fell apart after retirement mainly because he was far too generous with all of his friends and family when it came to money.
He made $110 million throughout his stellar NBA career and was a lot of fun to watch, but somehow managed to squander his entire NBA earnings soon after retirement.
It is reported that he would provide cash allowances on a monthly basis for over 70 friends and relatives which is extremely generous, but also incredibly poor decision making. I can only imagine the total amount Walker handed out to all his friends and relatives during his career and after (plus how many of them are helping him now).
Having seven fancy and expensive vehicles probably did not help either, but they did not lose him $110 million.
14 Eddy Curry
Curry’s life off the basketball court has been extremely difficult since the murder of his ex-girlfriend and their 9-month-old daughter. It is 100% understandable to go through a rough patch after that and more than likely squander money in order to ease the pain.
However, that is not the reason Curry went broke. It once again comes down to poor decision making on his part. Below is a quick list of reasons Curry is broke while still playing pro basketball overseas:
-$17,000 per month on rent
-$30,000 per month on extras
-$6,000 per month on personal chef
-$16,000 per month for family spending
-$? On 12 purchased vehicles
-A $570,000 loan he took with 85% interest rate….wow!
13 Kenny Anderson
Despite playing 14 seasons in the NBA and earning $63 million over his career Anderson found himself broke after he retired. How does someone squander away so much money so fast?
In this case it was child support payments for seven children Anderson had with five different women. Poor decision making seems to be the number one money killer for athletes in retirement and having kids in each of your favorite cities like Anderson is a perfect example.
12 Derrick Coleman
Coleman did not fall apart after retirement because of expensive and unnecessary items, but because he simply put most of his money into poor real estate investments in Detroit.
I understand trying to contribute to your city, but they have to be smart financial decisions that will not backfire and leave you with nothing. Unfortunately for Coleman, the recession hit Detroit and his bank account hard leaving him with nearly $5 million of debt.
11 Terrell Owens
Owens will more than likely go down as one of the greatest receivers in NFL history after his stellar career and often entertaining interviews. Unfortunately, he is no longer the happy and sometimes a bit off the wall self. After a not so ceremonial retirement because he could not get on an NFL roster he has been steadily heading in a downward spiral.
Money mismanagement, a clever and scheming financial adviser who squandered T.O's finances and multiple failed attempts at resurgence have caused massive grief to the former superstar.
10 Allen Iverson
Iverson had an awesome NBA career and was extremely entertaining to watch. However, his antics were more of a premonition to his poor financial decision making.
After making well over $200 million from NBA contracts and endorsement deals, Iverson has still managed to somehow lose it all. Like Antoine Walker, Iverson supported over 50 friends and family members financially during and after his career which quickly depleted his bank account.
He has been banned from multiple casinos as well and has tried to resurrect his career overseas. It is worth noting that he almost resorted to playing professional indoor soccer and was offered a contract with the Rochester Lancers.
9 Evander Holyfield
Like others on our list Holyfield squandered most of his (over) $200 million career earnings on friends and family who were looking for handouts.
He admits that he had a hard time simply saying no to people and that played a large role in his eventual demise financially. Lack of discipline and financial understanding cost Holyfield not just his career earnings, but the majority of his most prized memorabilia from his career along with his mansion.
8 Latrell Sprewell
Sprewell’s life may have begun to unravel well before he retired from the NBA. He is the only player in history to actually choke out his head coach, get suspended 68 games without pay and then come back only to turn down a deal with the Timberwolves for $21 million over three years.
To make things worse for Sprewell he stated that the offer was not enough to even feed his family and insulted not only the Timberwolves, but the NBA as well.
That was the final straw for Sprewell’s NBA career and he remained unsigned that year riding off into the sunset on some of his “famous” Sprewell rims to never play in the league again.
7 Jose Conseco
Although Conseco had an outstanding baseball career (minus throwing everyone under the bus for steroids…) he has struggled mightily since retiring. He has consistently squandered his money and has tried his hand at multiple money making ideas.
These include, semi-pro baseball, Celebrity Apprentice, celebrity boxing and even mixed martial arts which have all resulted in failure.
He left the MLB with a sour taste in the mouths of everyone and has simply been convincing people to like him even less since retiring.
6 Mike Tyson
We all knew that Mike Tyson would make this list as his life post retirement has spiraled downhill pretty fast for nearly every reason mentioned throughout the list.
Tyson may have begun his descent well before he officially retired and has had one of the most up and down lives out of everyone on the list. He also squandered away significantly more money than everyone on this list.
Where do I start? Biting Holyfield’s ear in a boxing match, being convicted of rape, purchasing Bengal Tigers, pigeon racing, $5 million mansions, random ridiculous spending, attempted boxing comebacks?
5 Lawrence Taylor
Taylor was an absolutely dominant force on the football field and finished his NFL career destined to be in the Pro Football Hall of Fame.
He had many off the field issues during and after his career, but seemed to be putting the pieces to his life back together until 2009.
That year Taylor was involved in a hit and run where he fled the scene and was later arrested.
4 Denny McLain
This guy decided to be a criminal when he retired from professional baseball after an excellent career which resulted in two Cy Young Awards.
Since retiring McLain has been imprisoned multiple times for various crimes including drug trafficking, embezzlement, mail fraud, theft and was even involved in racketeering crimes with gangster John Gotti Jr.
3 Lenny Dykstra
Dykstra had an excellent professional baseball career, but was an absolute failure in nearly every aspect once he retired.
In the beginning he had a successful chain of car washes that were making good money, but he decided to sell them and invest his money into an all-in-one business called The Players Club which featured a magazine, charter jet service as well as a brokerage/investment service for professional athletes.
The Players Club was an epic fail which resulted in him not only losing the business, but losing the Wayne Gretzky mansion he purchased for over $18 million and left in ruins when he simply abandoned it because he could no longer pay the bills.
Since then he has been involved in multiple fraud cases and filed bankruptcy after being well over $20 million in debt to creditors alone, not including his former employees, business partners and others.
2 O.J. Simpson
1 Ugueth Urbina
Most people may not remember Urbina for his professional baseball career as a decent pitcher because of his immediate downfall just a month after retirement.
Rather than squandering his money and making poor financial decisions like nearly everyone on the list he decided to make the worst decision of his life.
Apparently one month of no baseball was enough to make Urbina lose his mind back in 2005. He attacked workers on his farm with a machete and proceeded to pour gasoline on them attempting to burn them alive.
This allegedly happened because Urbina thought one of them stole his gun. He was convicted of attempted murder and sentenced to over 14 years in prison.
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