Wouldn't life be easier if you were a millionaire or, better yet, a multi-millionaire? Maybe not. It hasn't worked for some of the most highly-paid professional athletes in recent history. Some partied too hard. Others had big hearts for their friends and families. Most had little to no experience managing large sums of money. These and more challenges caused havoc in the personal and professional lives some of the biggest athletes around. Let's take a look at some of the accomplishments, spending habits, debts, and results of some of the most well-known professional athletes in three different sports.

Key Takeaways

  • Some of the most successful athletes who have squandered away their fortunes each share common themes in their stories: Bankruptcy, substance abuse, and domestic violence.
  • Most athletes have a small window of time in their professional athletic careers and are expected to live highly extravagant lifestyles.
  • Former NFL player Vince Young was known for indulging in expensive alcohol and meals.
  • John Daly spent millions of money he earned as a golfer on gambling.
  • Dennis Rodman, one the NBA's most well-known and flamboyant players, was rumored to be broke a year after he retired from the league.

Problems With High-Profile Lifestyles

If you look at some of the biggest successes-turned-financial failures in the sports world, there are some common themes and elements to each of these athletes' stories. Bankruptcy, substance abuse, and domestic violence are all common issues for current and former pro football players that the NFL requires for all rookies to attend a four-day symposium each year. Along with orientation, the players get lectures on professional responsibility, personal finance, substance abuse, community engagement, and other off-the-field challenges they will probably encounter.

The inability of professional athletes to manage their finances responsibly is a serious concern for the NFL. In an ESPN documentary called "Broke," it was estimated that 78% of NFL players are out of money in less than two years after leaving the game.

One of the main reasons why these athletes go belly up is the small window of time in which they can make money. The amount of time they have in their professional athletic careers is small compared to other professionals who may have as many as 50 years to work to amass their fortunes. The other driver is the need for extravagance. Because those who are at the top of their game end up becoming pop culture icons, they are expected to live up to a certain lifestyle. Their naivety—both financial and otherwise—can lead to disastrous results.

Professional athletes are often pressured by the small window of time to make it during their careers, as well as the expectations to live highly posh lifestyles.

Vince Young (NFL)

After winning the Rose Bowl Most Valuable Player (MVP) award twice, Vince Young was one of the most highly anticipated picks going into the 2006 NFL draft. He was selected as the third overall pick by the Tennessee Titans and signed a $58 million contract. He played six years in the NFL for three different teams.

During his playing years, he was known for indulging in $600 shots of cognac at Morton's after home games. He spent $5,000 per week at the Cheesecake Factory, and once purchased 120 out of 130 seats on a commercial airline flight. He was also hit with a judgment from a payday loan company, which Young contested in court.

Vince claims to have been ripped off by his agent and financial advisor. He was unsigned, running out of money, and looking for work soon after his release by the Buffalo Bills in 2012. Young announced his retirement from the game in 2014, but said he would reconsider if he was given the right offer. He signed with the Canadian Football League's (CFL's) Saskatchewan Roughriders in 2017, but was released because of a torn hamstring. He was also signed on to work with the University of Texas in 2014 as a development officer in the school's community engagement division. Young was let go by the institution in 2019.

There was at least one financial success: Young opened the Vince Young Steakhouse in Austin, Texas, and it's still open today. However, the restaurant is now owned by a local husband-and-wife team. Young filed for bankruptcy in late 2016.

John Daly (PGA)

John Daly is a California-born golfer who joined the PGA Tour in 1987. He's known for his long drives from the tee, his careless attitude, and a rocky personal life. He's the only golfer to win two major championships and never be invited to play in the Ryder Cup.

Daly's career earnings exceeded $9 million. But according to his autobiography, "John Daly: My Life in and out of the Rough," he lost somewhere between $50 million and $60 million gambling. After winning $750,000 at a San Francisco golf tournament in 2005, he immediately went to Las Vegas and lost over $1.5 million playing $5,000 slot machines at casinos.

He also claims he drank a fifth of Jack Daniels each day when he was 23 and on the PGA Tour. John battled his alcohol problem until 2008 when he made a commitment to stop drinking.

Married four times, Daly says he now only plays the $50 or $100 slot machines. There's also a website where fans can learn more about the former PGA athlete. Enthusiasts can also join the John Daly fan club and go through the online store to buy merchandise and memorabilia.

Dennis Rodman (NBA)

He's one of the most notorious basketball players to ever wear an NBA uniform. Dennis the Menace was known for his colorful hair and tattoos, his fierce rebounding and defense, and his habit of wearing a dress off the court.

He played on five-time NBA Champion team Chicago Bulls with Michael Jordan and Scottie Pippen. He was a seven-time rebounding champion.

By the time he retired from the NBA in 2011, his career earnings were estimated at about $27 million, not including sponsorships and personal appearances. A year later, he was rumored to be flat broke.

Married and divorced three times, Rodman fell behind on his child support payments totaling more than $860,000. He spent millions of dollars on a heavy metal record collection that took up two-thirds of the space in his $8.7-million Malibu estate. It's said that he would consider selling one or both kidneys to avoid selling his collection.

Rodman has since tried for second careers in reality television and pro wrestling. But he is perhaps best known today for his oddball friendship with North Korean dictator Kim Jong-un.

The Bottom Line

Former NFL star Warren Sapp said that some of the best off-the-field advice he ever got was from former coach Tony Dungy. These were Dungy's five points, in Warren's words:

  • Don't stay out past 1 a.m.
  • Don't go more than 15 mph over the speed limit
  • Avoid drugs and alcohol
  • Weapons will get you in trouble
  • Be cautious of women you know too well or not well enough

Sapp attended the 2012 rookie symposium to share these thoughts with the incoming rookie class, saying: "When the arrest does come, you can be sure three out of these five will come with it."