Expectations were high for Kenny Anderson after setting the ACC ablaze over two years at Georgia Tech. The New Jersey Nets made Anderson the No. 2 overall pick in the 1991 NBA Draft. By Year 3, Anderson was named an NBA All-Star which led to him securing several endorsement deals. While Anderson’s future looked bright, he failed to take the next step into superstardom. The lefty guard plateaued at a young age, and wound up playing for nine NBA teams before leaving the NBA for Lithuania in 2005.
Anderson’s off-the-court habits may have cost him a Hall of Fame career (in addition to nearly all of his assets). It’s no secret Anderson enjoyed splurging on expensive items. He owned a fleet of cars and routinely indulged in the nightlife of whichever city he happened to be playing in. Anderson’s expenses (which included paying child support for seven kids) eventually became too much. After making over $63 million during his 14-year NBA career, Anderson filed for bankruptcy shortly after playing his final NBA game. Fortunately, Anderson was able to rebound and is now the head basketball coach at Fisk University.
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Delonte West was a solid contributor over his eight-year NBA career. After lighting it up at St. Joseph’s with Jameer Nelson, West was a first-round pick of the Boston Celtics. The scrappy guard made a name for himself as a pesky defender and reliable three-point shooter. West would end up being traded to the Cleveland Cavaliers where he made 38 playoff appearances alongside LeBron James. After a short-lived reunion in Boston, West signed with the defending champion Dallas Mavericks following the 2011 NBA lockout. It would end up being West’s final season in the NBA. He was just 28 years old.
West blew through the $16 million he made during his NBA career in rapid fashion. The former NBA starter was reportedly homeless just two years ago. He was eventually checked into a rehab facility after being picked up at a gas station by Mavericks owner Mark Cuban. In 2021, West was arrested again after an incident outside of a Florida police department. In an attempt to get his life back on track, West is reportedly training to join Ice Cube’s Big 3 basketball league.
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Chris Washburn went from being the No. 3 overall pick to being banned from the league in the blink of an eye. The Golden State Warriors had high hopes for Washburn following his remarkable sophomore season at NC State. The team chose to overlook Washburn’s reportedly poor work ethic and checkered past (Washburn was caught stealing a stereo and was sentenced to 46 hours of jailtime and a five-year probation). The 6-foot-11 center was a tremendous athlete, but could never get on the right path.
In 1989, Washburn was banned from the league after failing his third drug test in three years. Washburn had previously checked himself into rehab after revealing a cocaine problem. After a quick soiree overseas, Washburn returned to the States where he began living in abandoned buildings around Houston, Texas. It was revealed that Washburn was forced to eat out of garbage bins for meals. During a podcast in 2016, Washburn said, “My lowest came when I was in prison. They asked me to play on the prison basketball team…I wasn’t even starting in damn penitentiary. I was coming off the bench.”
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Most will remember Rick Mahorn as one of the enforcers for the “Bad Boy” Detroit Pistons teams of the late 1980s. Mahorn stuck around in the league for quite some time due to his worth as a backup big man. He played all the way up until he was 40 before finally calling it quits in 1999. By the time it was over, Mahorn had earned over $8 million during his tenure in the league.
Turns out, the former NBA Champion wasn’t the best at managing his money. Mahorn filed for bankruptcy in 2010 following a near 20-year NBA career and several years as a WNBA coach. At the time, Mahorn reportedly owed over $200,000 to the IRS. He’s since worked his way back, and currently holds a position as a TV broadcaster for the Pistons.
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Williams is perhaps better known today for his work on reality television more than his 12-year NBA career. That’s because Williams was a member of the popular VH1 show title Basketball Wives alongside his now ex-wife Jennifer. Williams played for seven teams in his career, most notably spending seven seasons with the Boston Celtics. The New Jersey forward made nearly $40 million during his playing days.
In 2014, Williams claimed to be homeless and without enough money to pay for basic needs. At this time, Williams reportedly owed over $24,000 in child’s support, but didn’t have enough money to pay for a lawyer. There haven’t been any recent reports of Williams getting back on his feet.
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Undrafted out of Nebraska in 1996, Erick Strickland caught on with the Dallas Mavericks where he would spend the first-half of his NBA career. The undersized two-guard went on to play nine years in the league — an impressive feat for an undrafted player. He mostly operated as a reserve, but made some starts over his career in a pinch. Strickland was clearly valued for his ability to attack multiple roles, and was compensated as such. Over his career, Strickland earned over $13 million in contracts.
Strickland’s fortune dried up in a hurry after a disastrous real estate decision. After being proposed a deal by a close friend, Strickland had his father — a retired Air Force lieutenant — look over the deal. Unbeknownst to son and father, the plot of land was worth far less than they originally were made to believe. Strickland was forced to take a massive hit. It was later revealed that the friend earned a cut of the deal which led to a falling out. Remember, always check the fine print!
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Clifford Robinson enjoyed a lengthy NBA career as a role player for a number of teams. After being selected in the second round of the 1989 NBA Draft, Robinson joined the Portland Trail Blazers — where he would spend the first nine years of his career. Following his rookie campaign, Robinson inked a five-year extension with the Blazers worth $12.7 million — a significant raise from his rookie deal. Robinson eventually was named an All-Star in 2004, and was once the tallest player (6-foot-10) to have made more than 1,000 three-pointers in a career (since matched by Dirk Nowitzki and Rashard Lewis).
Despite hauling in over $61 million in salary during his playing days, it was clear that Robinson wasn’t particularly adept at saving money. He filed for bankruptcy in 2009 — a year after he retired — with reports that he owed over $12 million to creditors. Robinson was forced to sell his house in Oregon and find work. He began making television appearances, including being a contestant on a season of Survivor. Unfortunately, Robinson passed away in 2020 after a battle with lymphoma.
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After winning an ABA title with the Kentucky Colonels, Illinois native Dan Issel made the leap to the NBA where he joined the Denver Nuggets. Issel would play for the Nuggets for 11 seasons, and later became the head coach of the team. As head coach, Issel was suspended (and later fired) for shouting a racial slur at a heckling fan.
In 2009, Issel filed for bankruptcy. He was forced to sell most of his assets, including his 1975 ABA All-Star ring in addition to his 1989 NBA All-Star ring. Issel reportedly owed over $4.5 million to creditors, including multiple family members. Couldn’t have happened to a better guy…
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Christian Laettner rose to fame as the antagonistic star of the Duke Blue Devils in the early 1990s. He then parlayed his storied college career into a roster spot on the 1992 “Dream Team”. Laettner would go on to play 13 years in the NBA, making stops in Minnesota, Washington, Atlanta, Detroit, Dallas and Miami before calling it quits in 2005. Over the course of his playing days, Laettner gained connections which would later impact his business life.
Following his playing career, Laettner pursued several business ventures alongside fellow Duke alum and teammate Brian Davis. In 2016, Laettner was sued for $14 million by a group of investors. Among those creditors included former NFL running back Jonathan Stewart and linebacker Ernie Sims. In addition, the group pushed for Laettner to file for bankruptcy. Laettner also had to pay NBA star Scottie Pippen $2.5 million and NFL Pro Bowler Shawne Merriman $3.7 million for failed investments.
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For a time, it appeared as if Vin Baker was going to be the next, great power forward. The Hartford product burst out of the gates for the Milwaukee Bucks, securing four All-Star nods in his first five seasons. Baker was then traded to SuperSonics in the deal that shipped Shawn Kemp out of Seattle. Baker’s career slowly unraveled from there, though he did secure a sizable extension prior to his decline. In total, Baker earned just under $100 million during his time in the league.
Baker battled addiction during his time in the league, which ultimately is cited as the reason for his regression as a player. His alcoholism led to the star developing a gambling addiction. Baker burnt through his fortune with gambling losses and failed investments. Baker has since gotten back on his feet, and has been sober since 2011. He was hired as an assistant coach for the Milwaukee Bucks in 2019, and was a member of the staff when the team won the NBA title in ’21.
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It’s hard not to think Darius Miles left some meat on the bone as it pertains to his NBA career. Athletically gifted and uniquely skilled, Miles was one of the top prospects in the 2000 NBA Draft. Miles was expected to follow players like Kevin Garnett and Kobe Bryant who had both experienced near-immediate success after being drafted straight from high school. Though Miles showed flashes, he battled injuries and inconsistencies in what amounted to a rather disappointing career.
Still, Miles stuck around for a decade and earned nearly $62 million in salary for his efforts. That didn’t prevent him from filing for bankruptcy in 2016. Miles was forced to sell off his belongings, including an autographed LeBron James jersey. Making matters worse, Miles was one of 18 former NBA players charged with defrauding the league’s benefit plan by claiming fake medical expenses in 2021.
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Eddy Curry put the trust of his finances in the wrong hands. The former NBA starting center enjoyed an up-and-down career. After being drafted fourth overall in 2001, expectations were high for Curry — who joined the league straight out of high school. Curry played four years in Chicago before being shipped to New York in a massive trade. Curry exploded in Year 2 with the Knicks, averaging nearly 20 PPG on a sky-high field goal percentage.
The remainder of his career was riddled by injuries and a poor work ethic, but he did manage to earn $70 million over the course of 12 NBA seasons. However, Curry was hardly frugal and loved to spend money anyway he could. The big man drained the majority of his finances in peculiar ways — including paying over $1,000 monthly for his cable bill and $6,000 on a personal chef.
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Following his NBA career ending in 2008, Antoine Walker stumbled upon some dark times. In 2010, the former All-Star filed for bankruptcy after blowing through the $108 million he earned while playing in the NBA. A year later, Walker faced felony charges for knowingly issuing bounced checks to pay off casino debts.
Walker pled guilty and avoided prison time, but was put on probation and ordered to eventually pay his debts. Needing money, Walked attempted an NBA comeback but to no avail. While things were looking bleak for a moment, Walker has since turned his life around. He has a job as a broadcaster for FS1 and seems to have found some stability.
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In the same 1975 NBA Draft which saw high school phenom Darryl Dawkins get selected No. 5 overall by Philadelphia, another prep star’s name would be called just 14 picks later. Bill Willoughby, a New Jersey native, was selected 19th overall by the Atlanta Hawks after being one of the most sought-after high school players in the nation. The rangy wing played for six teams in eight seasons in the NBA, ending his career with averages of 6.0 PPG and 3.9 RPG.
Following his playing career, Willoughby’s life took a spiral downwards. He was allegedly swindled out of $1 million by his agents. Willoughby was arrested in 2016 for getting into a scuffle with police officers. The 58-year-old was charged with aggravated assault, resisting arrest, and possession of marijuana.
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Latrell Sprewell was a gifted player who squandered millions due to his volatile personality. Sprewell’s biggest mistake is also one that overshadows a strong NBA career. In 1997, Sprewell — while playing for the Golden State Warriors — was suspended after choking Warriors head coach P.J. Carlesmio during a practice. It’s reported that teammates were forced to step in and detain Sprewell in order to deescalate the situation. The NBA announced Sprewell would be suspended for a year, and the Warriors voided his contract (set to pay him $23.7 million over the next three years).
Being a talented player means teams will take a shot on you even after a horrifying transgression. The New York Knicks inked Sprewell to a multi-year deal the following offseason, and he later played for the Minnesota Timberwolves as well. However, making $97 million wasn’t enough for Spree to avoid money problems. Sprewell defaulted on his home in 2008 and was sued by a former girlfriend for a whopping $200 million.
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Stingy guard Mookie Blaylock enjoyed a lengthy NBA career thanks to his defensive prowess. Blaylock led the league in steals twice and is ranked No. 5 all-time in steals per game. He made six All-Defensive teams over his career, and was paid handsomely for his defensive effort. Over Blaylock’s 13-year career, he earned over $30 million in salaries.
In 2014, Blaylock pled guilty to vehicular manslaughter after colliding with a car head-on in his home-state of Georgia. A passenger in the other vehicle passed away. Blaylock was sentenced to 15 years in prison and faced several other penalties. He agreed to a plea deal which reduced his sentence to three years, though Blaylock’s life has taken a serious tumble since his retirement.
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Following an illustrious career at UNLV, Larry Johnson was expected to be the NBA’s next big thing. It didn’t quite go as planned, as Johnson failed to ever reach the status of a superstar. However, Johnson did manage to forge himself a decade-long career in the pros which included a pair of All-Star appearances and a Second-Team All-NBA selection.
After starting out as the No. 1 overall pick in Charlotte, Johnson joined forces with Patrick Ewing and New York Knicks for the latter half of his career. In total, Johnson earned a lucrative $83 million over his NBA playing days. Not to mention the money he earned as “Grandmama” in those old Converse commercials. It wasn’t enough to keep Johnson in the positive, however, as he eventually filed for bankruptcy in 2015. He was forced to surrender his home in Orange County (worth over $800,000 at the time) to one of his child’s mothers.
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Shawn Kemp’s career is perhaps one of the greatest “what if’s?” in NBA history. The Reign Man was an insanely gifted basketball player. Kemp possessed jaw-dropping athleticism which allowed him to perform some of the most impressive dunks we’ve ever seen. His synergy with point guard Gary Payton was a sight to behold. Kemp’s career began to spiral after he was traded to Cleveland in 1998, though he enjoyed a 14-year NBA career and made six All-Star teams.
Kemp earned over $90 million from his NBA contracts, and received a massive payday from his sponsorship deal with Reebok. However, as recently as 2021, Kemp’s reported net worth had shrunk to just $5 million. This is primarily due to several failed business ventures, including a sports bar in Seattle which shut down in 2015. In 2020, Kemp opened a cannabis dispensary named Shawn Kemp’s Cannabis.
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Glen Rice was a sharpshooter during his playing career, but wasn’t nearly as accurate when it came to financial decisions. After a career which spanned 15 seasons, Rice earned approximately $68 million from his NBA contracts. For most people, that would be more than enough to sustain for the remainder of their lives. However, Rice burnt through that cash quicker than he could launch a three-pointer from the perimeter.
After spending most of his earnings, Rice was reportedly broke as recently as 2016. As a result, Rice was granted a lower child support payment in order to deal with his debt. Rice’s main sources of income are autograph signings and basketball camps as he attempts to get back on track.
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Dennis Rodman was a Hall of Famer in two sports…basketball and nightlife. The seven-time rebounding champion made over $27 million during his NBA career. In retrospect, Rodman would have made exponentially more money had he been around for today’s NBA. The all-world defender helped his team win five NBA Championships despite his tumultuous life off-the-court.
It should be noted that Rodman didn’t just spend all of his income on himself. The New Jersey native routinely gave out money to homeless people — sometimes handing people he came in contact with thousands of dollars at a time. Eventually, Rodman’s charitable ways caught up to him. While Rodman’s reported net worth of $500,000 is nothing to scoff at, it’s a far-cry from what he was making as a pro.
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Gilbert Arenas was known as an incredibly talented basketball player who didn’t always make the smartest decisions. Of course, among Arenas’ most famous blunders was when he was suspended for an entire season after bringing a loaded firearm into the Washington Wizards’ locker room. Arenas returned a year later, but was never the same player after battling several injuries. However, Arenas was, at one point, one of the highest-paid players in the league. Through seasons with the Warriors, Wizards, Magic and Grizzlies, Arenas earned $163 million in his playing career.
Arenas has always been known for having fierce spending habits. He was famously “homeless” as a rookie after spending his entire first-year contract. In 2016, Arenas claimed to have burnt through his entire $111 million contract given to him by the Washington Wizards. In a video filmed by TMZ, Arenas said he didn’t have enough money to fund his children’s private school. Quite the tumble for a player who formerly signed a max-contract in the NBA.
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Not even six-time NBA champions are impervious to losing their fortune. Take for example, former Chicago Bulls all-time great Scottie Pippen who has taken several financial hits following his playing days. After earning over $110 million in his playing career, Pippen made a handful of decisions which caused a severe strain on his bank account. This included losing a large amount of cash after selling his home in Portland, as well as purchasing a private jet which needed over $1 million worth of repairs.
In total, Pippen reportedly lost over $27 million on poor investments. The Arkansas native never filed for bankruptcy, though he did attempt to sue a number of networks which implied he did. In 2011, Pippen sued CBS, CNBC, and several other news outlets for $1 million each for wrongfully claiming that he was broke. Nevertheless, Pippen is reportedly worth $50 million and recently launched his own brand of bourbon called Digits.
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The “Big Fundamental” trusted the wrong people with the fruits of his illustrious playing career. After winning five NBA championships and widely being considered the greatest power forward in NBA history, Duncan lost millions in failed investments. While going through paperwork during his divorce in 2013, Duncan noticed that his financial advisor had cost him nearly $25 million in a deal that went wrong.
Duncan was able to recoup some of that money after suing his former advisor. The court ordered Duncan to be paid $7.5 million in damages. The former San Antonio Spur made over $245 million during a 20-year playing career. After serving as an assistant coach on Gregg Popovich’s staff in San Antonio for the 2019-2020 season, Duncan has now left the game of basketball for good.
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Being one of the best players in the league, Charles Barkley was also one of the highest-paid players throughout his NBA career. Over 16 years in the NBA, Barkley earned $43.6 million in salary. Not to mention, Barkley was regularly featured in ad-campaigns and commercials thanks to his strong play and lively personality.
Sir Charles spent money as quickly as he earned it — sometimes, faster. Barkley had an affinity for gambling, and had no fear in putting up large sums of cash on a wager. Reportedly, Barkley had the ability to lose millions within a single day. Barkley has stated that he likely wagered (and lost) over $1 million on 30 separate occasions. Fortunately, Barkley was able to stay afloat and is now one of the highest-paid sports personalities on television.
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Allen Iverson had it all. The accolades, the shoe-deals, the multi-million dollar contracts. For a time, Iverson was the most marketable athlete in the sport. The “Answer” made over $154 million from contracts alone and even more from his sponsorship deal with Reebok. In 2009 — when Iverson was far beyond his prime — he was still among the top-10 highest-paid players in the league. Though he earned plenty of money, Iverson spent it just as fast. The former NBA MVP was a regular at gentleman’s clubs across the country (where he would drop up to $40,000 each visit), and built up a hefty collection of houses, cars, and jewelry.
In 2013, Iverson lost his home in Atlanta after defaulting on his mortgage. While he was severely low on funds, Iverson was saved by a unique clause in his Reebok deal. In 2001, Iverson signed a lifetime deal with the shoe and apparel manufacturer which included payments all the way up until 2030. Iverson receives $800,000 per year from Reebok, and will gain access to a trust fund in 2030 worth a whopping $32 million. Whoever negotiated this deal for the former NBA star deserves a medal.
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