10 Rich Athletes Who Served Time in Prison

Italian motorbike racer Valentino Rossi once said, “I don't like being famous - it's like a prison.” Well, several famous athletes seem to have taken the quote to a whole new level, actually spending time in jail.

Yes, while these prominent sportsmen and women were already rolling in dough and could have simply enjoyed their fame and fortune, they somehow managed to find themselves serving time instead. Their charges run the gamut from being as dumb as drug trafficking to as serious as murder, but what they all have in common is that each of these incidents left a black spot on what would have otherwise been successful and noteworthy careers.

But these people are only human after all, and everyone makes mistakes – theirs, however, made just a little bit more regrettable by the stature and money they had to ultimately sacrifice after being ordered to pay their dues in a cell. For some of them, their punishment spelled the end of their lives as athletes. Others bounced back and continued to move forward with their careers. Whatever the case may be, here are 10 top athletes who had to go to spend time in the slammer.

10 Marion Jones – Track & Field / Career Earnings: $12 Million

After having won 5 gold medals, Marion Jones was the darling of the 2000 Summer Olympics held in Sydney Australia. But just seven years later, she turned into one of America’s greatest sports embarrassments after she admitted to using performance-enhancing steroids throughout most of her career. As a result, Jones had to surrender all medals and prizes dating back to September of 2000, the money estimated at around $700,000.

Actually, rumours of her using banned substances had hounded Jones throughout her career, beginning when she was just starting to make her mark as an athlete in high school. Despite her repeated denials, it didn't help her cause that she worked with coaches and trainers known to supply their athletes with illegal substances, and had children with sprinter Tim Montgomery and shot putter C.J. Hunter – both involved in investigations on steroid abuse.

Aside from the penalties resulting from her steroid use and lying about it under oath, Jones was also found guilty of being involved in a check-fraud case and was sentenced to serve six months in jail. She began her sentence on March 7, 2008 and was released later that year on September 5.

9 O.J. Simpson – American Football / Career Earnings: $19 Million

Born Orenthal James Simpson and nicknamed "The Juice," O.J. debuted in the AFL after he was picked first in the 1969 rookie draft by the Buffalo Bills, a team he would play with until 1977. While he struggled in his first three seasons, in 1973 he became the first professional football player to rush for more than 2,000 yards in one season. Today Simpson remains the only player to have ever achieved the mark in a 14-game season. It is partly because of this record that in 1985, Simpson was inducted into the Pro Football Hall of Fame during his first year of eligibility.

Even before his retirement from football, Simpson had embarked on a successful film career, the highlight of which was his supporting role in “The Naked Gun” comedy trilogy. In fact, the football superstar would start his own film production company, Orenthal Productions.

Throughout his sports and movie career, Simpson lived the life, raking in the money and enjoying his fame and fortune. However, all of this was interrupted in 1995 when he was tried in a widely publicized case involving the 1994 murder of Ronald Goldman and O.J.’s ex-wife, Nicole Brown Simpson. O.J. would eventually be acquitted of the criminal charges, but in 1997, a civil court decided against Simpson, finding him responsible for the wrongful deaths of the two victims and ordering him to pay $33.5 million, of which he has paid very little.

After the whole murder case brouhaha, Simpson got into trouble with the law several more times, including a battery and burglary charge in 2001 for which he was acquitted, and a case involving stealing broadcast signals from DirecTV, for which he was made to pay more than $33,000. It was in September of 2008 that Simpson earned jail time after being found guilty of numerous felonies, including kidnapping and armed robbery in Las Vegas, Nevada. The sentence: imprisonment for 33 years, including a minimum of nine without parole.

8 Travis Henry – American Football / Career Earnings: $20 Million

Travis Henry is a former NFL running back who in 2001 was drafted in the second round by the Buffalo Bills. Henry would become the fourth-leading rusher in the history of the team with 3,847 yards and 27 touchdowns. After 4 years, he was traded to the Tennessee Titans where he broke the 1,000-yard mark but also served a suspension for substance abuse. Then in 2007, this time with the Denver Broncos, Henry faced charges of marijuana use for which he was eventually cleared after winning his appeal.

However, 2008 was the worst for Henry. After restructing his contract with the Broncos with the intention “to make it right” with the team, he was released just one year into his five-year, $22.5-million deal. Ironically, later that year he once again tested positive for marijuana and was suspended indefinitely. Worse, in September of 2008 Henry was arrested for drug trafficking for which he reached a plea agreement requiring him to serve ten years to life behind bars and to pay $4 million in fines.

In 2009 Henry was sentenced to three years in federal prison for financing a cocaine trafficking operation.

7 J.R. Smith – Basketball / Career Earnings: $34 Million

Earl Joseph "J. R." Smith III is at the moment best remembered for being named the NBA Sixth Man of the Year for the 2012-13 season. But serving prison time in the midst of his basketball career is also in the talented superstar’s history.

Over his career, Smith played for the New Orleans Hornets, the Denver Nuggets and the Zhejiang Golden Bulls of the Chinese Basketball Association. However, it was in his current stint with the New York Knicks beginning in 2012 that J.R. has made the most waves.

Smith signed with the Knicks under the bi-annual exception worth $2.4 million, allowing the team to greatly improve and earning himself another $2.8 million contract with a player option. In July 2013, Smith re-signed with the Knicks, the contract reported to be worth $17.95 million over three years. Actually, other teams had made bigger offers, but he chose to remain with New York because he believed it was with the Knicks that he had a better chance of winning a championship.

Unfortunately, just 4 days after the contract signing, Smith had to undergo surgery to repair a torn meniscus and a patellar tendon, both in his left knee. To make things worse, in September 2013, Smith was suspended for five games because he was found to have violated the NBA's anti-drug program.

It was way before all this that Smith had his first brush with the law. On June 9, 2007, Smith, along with two passengers, was injured in a car accident in New Jersey when the SUV Smith was driving collided with another car after running a stop sign, ejecting Smith and killing passenger Andre Bell.

6 Charles Barkley – Basketball / Career Earnings: $40 Million

Today, Charles Barkley is one of the prominent analysts on the NBA channel. But before that, Sir Charles was considered one of the NBA’s most dominating power forwards ever. He was an 11-time all-star from 1987-1997, won two gold medals for the United States in Olympic basketball, and was hailed as the league’s most valuable player in 1993. As a result of his achievements, Barkley’s last year of play in the NBA as a member of the Houston Rockets earned him $9 million, his largest annual paycheck.

Outside of his accomplishments as a player, Barkley was also regarded as one of the most outspoken and controversial athletes to have ever played basketball. He was very vocal on his opinion that athletes shouldn’t be considered role models, and perhaps the “Round Mound of Rebound” made his own life an example of his belief by often getting into fights with players, breaking a man’s nose after a game, and throwing another man through a glass window. Furthermore, Barkley is an admitted gambling addict, revealing that he once lost $2.5 million in six hours while playing blackjack and losing another $7.5 million in other gambling ventures.

Perhaps the last nail in the coffin for Barkley's reputation as a role model was a DUI arrest after he was caught running a stop sign on the last day of 2008. Barkley pleaded guilty to one count of running a red light and two DUI-related charges. The original sentence was 10 days in jail but Barkley only served three.

5 Jayson Williams – Basketball / Career Earnings: $63 Million

Jayson Williams played for the Philadelphia 76ers from 1990-1992 and for the New Jersey Nets from 1992-1999 and was an NBA All-Star in 1998. All throughout his career, Williams' star continued to rise causing his starting annual salary to balloon from just $500,000 to more than $11 million in his final year of play. Sadly, Williams will likely be remembered more for his legal struggles rather than his basketball skills.

Williams' brushes with the law began in 2002 when while playing with a shotgun, he killed a 55-year-old limousine driver. He was sentenced to 5 years in jail, of which he served 8 months. Then, in 2009, the former NBA-All Star became suicidal and violent, forcing officers to stun him with a taser so he could be taken to a hospital.

4 Michael Vick – American Football / Career Earnings: $130 Million

Michael Vick is no doubt an NFL superstar, having been named 2001 Toyota Gator Bowl MVP, winning the Best NFL Player ESPY Award in 2003 and being the all-time leading rusher for quarterbacks with 5,219 yards in his 5 years with the Atlanta Falcons and 4 years-and-counting with the Philadelphia Eagles.

In the middle of his storied NFL career, however, Vick pleaded guilty to being part of a dog fighting operation. In 2007 he was suspended indefinitely without pay for violating the league’s player conduct policy and was released by the Falcons who were reimbursed close to $20 million of Vick's $37 million bonus.

To make matters worse, Vick tested positive for marijuana in a random drug test while free on bail, a violation of the conditions of his release while awaiting sentencing. This would eventually result in a 23-month stay in federal prison.

3 Allen Iverson – Basketball / Career Earnings: $154 Million

Nicknamed “A.I.”, “The Answer” and “King Cross”, Allen Iverson was the number one pick for Philadelphia in the 1996 NBA Draft. He justified the decision by being named Rookie of the Year and would later be an eleven-time NBA All-Star and the All-Star MVP Award recipient in 2001 and 2005. He also won the NBA scoring title on four separate occasions and the NBA Most Valuable Player award for the 2000-2001 season.

Before all of those accomplishments, however, Iverson had served four months in prison, a penalty stemming from a “whites vs. blacks” altercation in a bowling alley, where Iverson allegedly struck a woman in the head with a chair. The sentence was actually for 15 years, but Iverson was granted clemency by the governor of Virginia.

2 Mike Tyson – Boxing / Career Earnings: $300 Million

Michael Gerard "Mike" Tyson was the youngest boxer ever to win the WBC, WBA and IBF heavyweight titles, at only 20 years old. At one time the undisputed heavyweight champion of the world, Tyson is to this day the only heavyweight boxer to have simultaneously held the WBA, WBC and IBF titles.

However, in 1992 Tyson was found guilty of raping 18-year-old beauty contestant Desiree Washington and was sentenced to six years in prison but he was released after serving only three.

After his release, Tyson made a comeback, successfully winning the WBC and WBA titles, but he would lose the WBA crown to Evander Holyfield in 1996 by an 11th round TKO. In 1997, their rematch ended when Tyson was disqualified for biting a piece off of Holyfield's ear.

Furthermore, despite having earned over $300 million throughout his career, Tyson was forced to declare bankruptcy in 2003.

1 Floyd Mayweather, Jr. – Boxing / Career Earnings: $350 Million

Floyd Mayweather Jr., actually born Floyd Joy Sinclair, is arguably the best pound-for-pound boxer ever, being currently undefeated in 45 bouts and having won five-division world championships, eight world titles and the lineal championship in three different weight classes.

Among the many big names Mayweather has defeated are Diego Corrales, Oscar De La Hoya, Ricky Hatton, Juan Manuel Marquez, Shane Mosley, Victor Ortiz, Miguel Cotto and Saul Alvarez.

These accomplishments have made “Money” Mayweather an incredible amount of cash, allowing him to top the Forbes and Sports Illustrated lists of the highest-paid athletes of 2012.

However, despite his other nickname, “Pretty Boy”, there’s something quite un-pretty about his past. Since 2002, Mayweather has been tried for various counts of battery against women, misdemeanors, robbery and threats to his children. This resulted in various fines, hours of community service and time in a county jail for which he was released on August 2012.

His dark past hasn’t seemed to hurt his earning capacity, though. Mayweather’s September 2013 fight against Saul Alvarez netted him a $50-million paycheck.

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10 Rich Athletes Who Served Time in Prison