Sidney Moncrief
When you’re considered to be one of the best guards in NBA history with the inaugural Defensive Player of the Year award already under your belt, what do you do to follow it up? If you’re Sidney Moncrief, you win the award again the next year! Across 11 years in the NBA, Moncrief is believed to have earned at least 7.2 million dollars, which is certainly nothing to scoff at. So, what happened, and where did it all go wrong for the 5-time NBA All-Star?
After retiring from the NBA, Moncrief opened a car dealership which quickly fell into debt. He filed for bankruptcy in 2005. Fortunately, Moncrief landed on his feet again after becoming an analyst for Fox Sports.
Erick Strickland
It’s not uncommon for NBA players to change franchises at multiple points in their careers, but Erick Strickland took this idea and ran with it all the way down the court. Across a career spanning nine seasons, Strickland signed with six different franchises. All of that must have paid off, though: after 68 games and a 12.8 PPG and 4.8 RPG average, Strickland earned over 13 million dollars. Unfortunately, a shady real estate deal would see his financials plummet.
Strickland was approached by someone he believed he could trust with a real estate deal he could not pass up on. The deal did not work out in the end, and Strickland lost his hard-earned money.
Dan Issel
The NBA history books make it clear that Dan Issel was one of the greatest players of all time for the Denver Nuggets. He’s a 7-time NBA All-Star, a 6-time All-ABA player, and a Basketball Hall of Famer. His stats never failed to impress throughout his career, and he averaged a 20.7 PPG in his ten seasons with the Nuggets. Outside of basketball, however, Issel ran into some money troubles.
In 2009, after trying to swing it as a business owner, Issel was forced to file for bankruptcy. He owed some 4.5 million dollars to at least 34 different creditors. To get himself back in good standing with the IRS, Issel unfortunately had to part with many of his prized possessions.
Eric Williams
When you’re coming up alongside someone like LeBron James, you’re going to need to give it your all in order to stand out. LeBron was - and still is - serious competition, but for the first few years of his career, it seemed that Eric Williams was up to the task. He had 15.0 PPG and 4.6 RPG averages during his second season with the Celtics, but after being injured during his third, some of his spark seemed to have gone out.
The hardships didn’t stop there, unfortunately. 10 years after his career ended, Williams found himself homeless and some $24,000 behind on child support payments.
Joe Smith
Some NBA careers can be devastatingly short, but Joe Smith enjoyed 16 years on the court and signed with 12 different franchises. Even towards the end of his career, Smith showed almost no signs of stopping, and his longevity made him a fan-favorite, particularly when he played for the Golden State Warriors. His illustrious career also netted him a cool 60 million dollars. It didn’t matter whether he was playing for Philly or Minnesota - Smith was raking in the dough.
Unfortunately, because Smith was always on the move, his spending got the better of him. He bought a home in every state he played in and went bust by 2018.
Darius Miles
Everyone loves an underdog, the young, plucky hero who rises up to face the odds stacked against them. The NBA has no deficit of underdog stories, and for a while, after his career began straight out of high school, Darius Miles looked to be the next big thing. Unfortunately, Miles was afflicted by numerous injuries, which cost him two seasons. He attempted a comeback in 2009, but by then, he was already a shell of his former self and could only strive for his previous athletic glory. Still, he earned 61 million dollars over the course of his career.
Unfortunately, after a few bad real estate deals, Miles couldn’t stay afloat. He filed for bankruptcy in 2016 but has managed to rebound somewhat since then.
Glen Rice
The NBA has seen numerous superstars come and go, and history tends to look on them favorably. That being said, former Hornets scorer and three-time NBA All-Star Glen Rice seems to have been somewhat forgotten. It’s a shame, too, because he was a proficient scorer when he played for the Heat and the Hornets, and when he moved to Charlotte, his career only soared to even greater heights. He peaked in 1997 with an average of 26.8 PPG.
Unfortunately, Rice’s shaky business dealings and stacking child support payments eventually put him in the red. He was only able to eke out a living through the sale and signing of various bits of memorabilia.
Derrick Coleman
The world of basketball is full of prodigies, many of which would enjoy long, successful careers and happy lives post-retirement. Derrick Coleman was one such player. He began his career with the New Jersey Nets, where he spent 5 years and won the NBA Rookie of the Year award, averaging a 18.4 PPG and 10.3 RPG. Afterward, he played for 10 more seasons with three different teams and eventually retired in 2005.
However, by 2010, Coleman filed for bankruptcy. Though it’s not clear exactly what caused his financial woes, it can probably be attributed to his lavish lifestyle and excessive partying.
Latrell Sprewell
The NBA is full of amazing talent, but occasionally, with that talent comes notoriety and infamy. Latrell Sprewell had his fair share of controversy, which hounded him throughout his career. His confrontational attitude was well known and well documented, particularly his strangling of head coach P.J. Carlesimo. None of that stopped Sprewell from earning nearly 100 million dollars over the course of his career. He was a terror on the court and his paycheck reflected that.
Three years after retirement, though, Sprewell spiraled into financial hell. Both his yacht and his home were repossessed after he failed to pay them off.
Antoine Walker
Standing at 6,8” might be tall by normal standards, but in the NBA, it’s a relatively short height, particularly if you’re playing as a power forward. That didn’t stop Antoine Walker, though. A 3-time NBA All-Star with the Boston Celtics, Walker was relentless and unyielding on the court and kept shooting until the clock struck zero. He also contributed to the Miami Heat winning an NBA title in 2006 in a major way. His career peaked with a 23.4 PPG and 8.9 RPG average, and he earned a little over 105 million dollars in total.
Unfortunately for Walker, a crippling gambling addiction and mounting legal fees meant that a lot of that money blew away with the wind.
Ray Williams
The basketball world makes obvious many of its heroes, but some can fly under the radar. Take Ray Williams, for example. He was never an All-Star, but that didn’t stop him from playing like one. He peaked with 20.0 PPG and 5.0 RPG averages and played for both the Knicks and the Nets back in the early 80s. He could be a real beast at times, which just goes to show that the NBA is full of stellar players, not all of whom receive the illustrious title of All-Star.
Sadly, after he retired in 1987, Williams fell on hard times and applied for his pension. That, too, was lost in a real estate scam. And while he eventually managed to get his affairs in order, he passed away in 2011 at 57.
Rick Mahorn
Not all heroes wear capes, and not all basketball champions are All-Stars. Rick Mahorn may not have received all the accolades and adoration that many of his successors would enjoy, but he worked hard on the court and gave it his all. Despite his phenomenal sportsmanship and dedication, Mahorn still received far less than many of today’s basketball players do. While still pocketing a neat 8 million dollars, he played in a time before basketball players earned such lucrative salaries.
Despite this, Mahorn managed to stay afloat for a solid 10 years after retirement. It was in 2011, however, after defaulting on his mortgage, that his fortunes took a turn for the worse.
Randy Brown
Not every player who hits the court is going to rake in stellar numbers. After all, every lead actor in a movie needs a supporting cast. In the world of basketball, this often means pulling players from the bench when the stars need a breather. And in that regard, Randy Brown performed his role perfectly. He never averaged more than 9.00 PPG or 3.5 RPG, but in his time with the Bulls, Brown could always mount a reliable defense while still pressuring the opposition. He also spent time with the Suns, Kings, and Celtics and earned over 15 million dollars over the course of his career.
Following his retirement, however, Brown tried his hand at becoming a business owner. After numerous deals fell through, he had to declare bankruptcy just five years after his career ended.
Mookie Blaylock
Trae Young may be considered the best point guard in the Atlanta Hawks’ history, but before he came along the Hawks relied on a man by the name of Mookie Blaylock. Blaylock was a demon on the court and won back-to-back steals titles in 1997 and 1998. He peaked with 14.9 PPG, 4.6 RPG, 7.3 APG, and 2.6 SPG averages, and to this day his steal record is unbeaten. In short, watching him play was never short of exciting.
Sadly, Blaylock battled numerous issues in his personal life, many of which left him in debt and crippled his post-NBA prospects. Following a devastating accident, Blaylock served time in prison and remains on probation to this day.
Clifford Robinson
Standing at 6 feet and 10 inches tall, the famed “Uncle Cliffy” was a sensation in the early 90s when he played for the Trailblazers. He was the NBA’s Man of the Year in 1993 and earned his first and only All-Star title the following year in 1994. With averages of 19.0 PPG and 5.5 RPG from 1993 through 1996, Robinson was a reliable scorer and well-respected athlete. He stayed on the court longer than many other players and only retired when he turned 40.
Unfortunately, his 60 million dollar earnings wouldn’t last long, and Robinson was forced to declare bankruptcy after finding himself 5 million dollars in debt. He turned his fortunes around somewhat with a marijuana business but sadly passed away after battling lymphoma.
Christian Laettner
This list of NBA players is full of All-Stars and fan favorites, but every sport breeds its fair share of infamous individuals. In basketball, Christian Laettner ranks up there with the sport’s most controversial figures. Despite his notoriety, Laettner enjoyed a pretty solid career with averages of 17.2 PPG and 8.1 RPG during his time with the Minnesota Timberwolves. He joined Detroit and Atlanta later on in his career, and when he was with the Hawks, he even managed to secure his first and only All-Star title in 1997.
Unfortunately, his bad business deals caught up to him following retirement and even landed him in a legal battle with fellow player Scottie Pippen.
Kenny Anderson
NBA careers typically don’t last too long, but former Nets player Kenny Anderson enjoyed an unbelievable 14 years on the court. His time with the Nets was probably the most illustrious point of his career, during which he earned his only All-Star title and averaged 15.3 PPG and 7.8 APG. He was a solid player and something of a rockstar - and the sporting world is full of them.
His superstar habits, however, did not come without their costs. Child support payments and numerous divorce settlements left Anderson bankrupt - even after earning over 60 million dollars during his long career.
Larry Johnson
Larry Johnson may very well be one of the NBA’s most beloved former players. Not only was he a fan favorite during his time with the Charlotte Hornets, he received even further acclaim when he made the move to the New York Knicks. His time with the Hornets was marked by averages of 19.2 PPG and 9.2 RPG, as well as two All-Star titles, while his time with the Knicks is marked by one of the greatest four-point plays in NBA history.
Sadly, Johnson’s career was cut short by a devastating back injury that required extensive surgery and hospitalization. In addition to mounting child support payments, his medical bills would cost him everything.
Shawn Kemp
If you were an NBA fan in the 90s, you will definitely remember Shawn Kemp. He almost single-handedly put Seattle basketball on the map. Every time you watched him, you got the sense that he was about to make some incredible play. From 1993 to 1998, he made six All-Star games and nearly won Seattle a championship in ‘96. His perfect balance of speed and strength pretty much guaranteed him superstar status - not to mention 96 million dollars.
Unfortunately, a slew of child support payments and other legal troubles put a dent in Kemp’s wallet, and he was forced to declare bankruptcy following his retirement from the NBA.
Vin Baker
The 90s gave rise to plenty of promising young stars, and Vin Baker enjoyed his fair share of acclaim throughout his career. He was exciting to watch, an underdog with real tenacity. In his heyday, Baker would average 21.0 PPG and 10.0 RPG. His Milwaukee teams could never quite seem to break into the playoffs, but once he joined Seattle later on, he got a true taste of the action. He was a three-time All-Star and played a devastating offensive game. All of this earned him plenty of admiration from fans and peers - as well as the ludicrous sum of 97 million dollars.
Sadly, Baker’s personal woes and struggles landed him in severe debt, and he was forced to turn to an old friend for help. Fortunately, he has since managed to turn his life around.
Shandon Anderson
Part of the appeal of the NBA for many players is the lifestyle it promises. For most, that includes a whole lot of partying and being able to eat whatever food you can get your hands on (provided you stay healthy, of course). For Shandon Anderson, though, that meant being able to pursue a vegetarian lifestyle. Though he was a great player in his time, Anderson is probably best remembered for being one of the few vegetarians in the NBA.
Following his retirement, Anderson pursued his vegetarian lifestyle even further, taking culinary courses and investing in a restaurant called Drink Art.
Wilt Chamberlain
Any list of NBA players, good or bad, wouldn’t be complete without mention of Wilt Chamberlain. With a staggering record 30 points per game - as well as a record 100-point game at one point - Chamberlain left an indelible mark, not just on basketball, but on sports history as a whole. His career took him from the Harlem Globetrotters all the way to the LA Lakers and cemented his status as one of the greatest players of all time.
Following on from his retirement, he pursued numerous ventures, becoming moderately successful at most, before passing away in 1999.
Tim Duncan
Another certified G.O.A.T, Tim Duncan’s career was nothing short of epic, and he played for the San Antonio Spurs, securing for the team five NBA championships and a couple of MVPs for himself. After two decades as one of the most prolific basketball players in history, he finally called it quits but would keep in shape as a martial artist. However, he would return to the world of basketball in another role, that of a coach for his team the Spurs, where he continues to enjoy success.
Unfortunately, he was not as successful in investments as he was in basketball, losing around $24 million. All of his investments either failed to return on their investment or went bankrupt. Ouch!
Michael Ray Richardson
This list is chock full of legends enough as it is, but how could we leave Michael Ray Richardson off the list? When it comes to NBA talent pre-1980s, Richardson ranks up there with Magic Johnson and Larry Bird. An all-around phenomenal talent, “Sugar Ray” could score with the best of them and mount a fantastic defense while doing it. The man was destined for NBA greatness, and while his career was cut short by a crippling drug dependence, he's still remembered fondly as one of the G.O.A.T’s.
Fortunately, Richardson's substance problems wouldn't last forever. After spending some time in the European League, he returned to Oklahoma to work as a certified substitute teacher and run a youth basketball clinic for underprivileged kids.
Darko Milicic
Not everyone who joins the NBA is guaranteed to have a stellar career. Some players come in, play well, and leave without much recognition. Darko Milicic was one such player. Drafted in 2001 right after little-known player LeBron James, Milicic spent 11 years on the court, playing consistently but not exceptionally. The simple truth of the matter was that the 7-foot tall Serbian just didn’t enjoy his time in the NBA, and when he retired in 2012, he sold his Pistons Championship ring and donated the proceeds to charity.
Feeling lost, he returned to Serbia and discovered his true calling as an apple farmer. Pretty much all of his NBA earnings went into his new gig. Hearty to the core, he is!
Shawn Bradley
In a sport dominated by super tall individuals, it can be pretty difficult to really stand out. Unless you’re Shawn Bradley, of course. Hailing from Brigham Young University, Bradley stood at over 7 feet tall and six inches. He wasn’t a particularly noteworthy scorer, but his defense game was strong, and he dominated the league in blocks for a time. He played for both the Nets and the Mavericks before subsequently retiring in 2005.
Following his NBA career, Bradley tried his hands at politics, running as a Republican candidate, but ultimately lost. He now runs a ranch in Utah and even owns a heavy machinery rental company.
Karl Malone
Playing in the NBA requires an immense amount of hard work and dedication. Some people have it, some people don’t, and Karl Malone falls squarely within the former category. His illustrious 19-year career was marked by his unstoppable presence - he amassed over 36,000 points during his time in the NBA. He also took home two MVP titles - all this thanks to his persistence and relentless pursuit of excellence on the court. Of course, that dedication extended to his career outside of basketball as well.
Following his retirement, Malone became an entrepreneur. He now owns several businesses, including car dealerships and a hunting outfit, and is unafraid of getting involved in the day-to-day affairs of his many enterprises.
Kevin Garnett
As far as NBA careers go, it’s hard to match Kevin Garnett. The man is regarded as one of the best power forwards in basketball history. Playing for teams such as the Minnesota Timberwolves and Boston Celtics, Garnett helped the latter bring home an NBA championship during his very first year with the team. His dominance was nigh-unmatched, and his ferocious skill and tenacity earned him several accolades, not least of which included 15 All-Star title selections and being named both Most Valuable Player (MVP) and Defensive Player of the Year.
Now retired from the NBA, Garnett hosts his own show called Area 21. He’s not far removed from the basketball world, and his show features lively discussions and coverage of current events in the NBA.
Adrian Dantley
We’ve said it before, and we’ll say it again: not all heroes wear capes. Some may even go completely unrecognized in their lifetime. Fortunately for Adrian Dantley, this is not the case. NBA historians will fondly remember this six-time All-Star who played for the Utah Jazz. He was a consistently excellent player and a two-time scoring champion as well. When he retired from the NBA for good in 1991, he probably had no shortage of prospects.
Unexpectedly, though, the former All-Star became a crossing guard. He was fulfilled in his new position, ensuring the safety of kids on their way to and from school.
Detlef Schrempf
Being an expat to the US comes with its fair share of challenges. That is, of course, unless you’re Detlef Schrempf. The German scorer quickly signed with the NBA shortly after immigrating. He then played for the Dallas Mavericks, the Indiana Pacers, and the Seattle SuperSonics in a career that lasted 16 years. Throughout his time on the court, Schrempf kept his head on his shoulders and his eye on the proverbial ball. And when he retired, he retained his level-headed decision-making.
Schrempf became a financial advisor and learned how to manage his wealth properly. He also worked as a business coach and an assistant coach for his former team, the Seattle SuperSonics.
Hakeem Olajuwon
The NBA has had a pretty diverse selection of superstars. In a list that includes such titans as many of the previous people on our list, it can be tough to stand out. Fortunately, Nigerian-born Hakeem Olajuwon had no trouble finding his feet. Though not American, Olajuwon gave the NBA his all, beginning his career in Houston with the Rockets. During his time, Olajuwon led the Rockets in back-to-back championships and earned numerous accolades himself, including NBA MVP, Defensive Player of the Year, and NBA Finals MVP.
Following on from his illustrious career in basketball, Olajuwon wasted no time in securing a new career as a real estate mogul, and he rakes in hefty amounts of money even today.
Bryant Reeves
The NBA, for all the glory that it brings, can be a harsh mistress. Occasionally, there comes along a talent that - while exceptional and promising - simply can’t cut it in the major leagues, and not for a lack of skill. Bryant Reeves was a promising player when he began his career with a stint with the Vancouver Grizzlies. Known as “Big Country” on the court, he was a persistent scorer and versatile athlete. Unfortunately, Reeves had to retire from the NBA shortly after his career began due to persistent back pain.
Luckily, that didn’t prevent Reeves from finding success elsewhere. He invested in a 300-acre cattle farm, all the way in Oklahoma, where he avoids the spotlight.
Maceo Baston
In the NBA, it’s not unheard of for players to move around throughout their careers. Some of the greatest players have signed with multiple teams. Testament to that fact is Maceo Baston, who enjoyed a 13-year career with multiple teams, not least of which included the Toronto Raptors and the Indiana Pacers. He left the NBA to join the Israeli league, where he found even more success, winning three championships. In 2001, he retired for good.
Since then, Baston has tried his hand at entrepreneurship, opening up a cupcake business with his wife, which has enjoyed immense popularity and success.
LaRue Martin
The NBA has no shortage of superstar stories, but the amount of faded careers is nearly as high. Take LaRue Martin, for example. He was a promising young player when he first signed with the NBA, becoming the number one draft pick and joining the Portland Trailblazers. Unfortunately, his dreams of superstardom faded quickly, and following his retirement, he joined the corporate world in an effort to provide for his family.
That effort paid off in the end. He now works as the UPS Illinois district public affairs and community services manager and still gives back to the world of basketball by being part of the National Basketball Retired Players Foundation.
Brandon Roy
As mentioned previously, the world of the NBA can be pretty unforgiving and rather ruthless at times. Take the story of Brandon Roy, for example. Though he started as a promising wing guard with prospects of entering the Hall of Fame (not to mention three All-Star titles under his belt), Roy’s career was cut short by a devastating knee injury that left him unable to continue his tenure with the NBA.
Fortunately, Roy landed back on his feet and now coaches basketball for his former high school. He takes pride in his work shaping future talents - and that, we believe, is worth all the titles in the world.