Celebrities Who Did Not Get So Lucky When Investing

Are we all financial geniuses right after school? We guess not, right? Everyone usually undergoes a series of financial setbacks and learning experiences before being considered geniuses in that area. Putting our money towards vessels that allow it to grow means that we are also taking risks that it may not succeed. What is critical is that the stakes are weighed carefully and that we could deal only with legitimate financial advisors.

Your favorite celebrities are not exceptions to that. The list below showcases Hollywood stars who have made investing errors. Why do you think they made poor financial choices? Many actors and actresses are very successful entrepreneurs, but they still fall victim to losses. From embarking on money schemes to poor money handling, read through the various items to find out more, learn from them, and not repeat the same money mistakes.

Michael Vick

Playing as a quarterback in 13 seasons of the National Football League, primarily with the Philadelphia Eagles and Atlanta Falcons, certainly made Michael Vick a veteran in the world of football. He started his career while he was in college at Virginia Tech. The Falcons selected him during the 2001 NFL Draft as their first choice, and it seems that the team made the right decision because Vick was able to transform the quarterback position with his superb rushing abilities.

While considered an expert in sports, Vick appeared to be a newbie in the world of investments. Reports showed that he had made a series of financial errors, including being involved in dogfighting. He also made a questionable purchase of an $85,000 worth of custom fish pond—the purpose of which was unclear. Was he going to sell the fish or consume them by himself?

Harvey Weinstein

As a producer, Harvey Weinstein has made some of the best films in the industry. He and his brother, Bob, are the investors and founders behind Miramax, which produced films like Heavenly Creatures, Shakespeare in Love, and Pulp Fiction. He was asked to leave the company later because lawyers filed several cases in court against him, and he now serves a sentence.

Apart from losing legal cases, Weinstein was also the victim of Kenneth Starr, who ran a Ponzi scheme and defrauded other celebrity clients such as Carly Simon, Sylvester Stallone, and Tom Brokaw. These personalities filed the necessary lawsuits, but it is not clear how they can recover the money and whether Starr has the money to give out in the first place. This incident would have served as a lesson for anyone to be cautious when trusting someone else with their hard-earned money.

Tom Brokaw

Now retired, Tom Brokaw has been a legend among journalists. He has served as the co-anchor of The Today Show and then as an anchor and managing editor of NBC Nightly News. He is also considered one of the Big Three news anchors of the 1980s, 1990s, and 2000s. Apart from being a TV journalist, he has also written several books discussing society in the 20th century and American history. Brokaw was also awarded the Presidential Medal of Freedom, given to him by Barack Obama.

Despite all the accolades, Brokaw was not immune to the effects of a Ponzi scheme and displayed a lack of money management skills. Along with other big stars, he fell victim to Kenneth Starr’s scheming and set aside a portion of his money for the supposed wealth-generating move. It turned out to be a scam, and there is very little chance he and the rest would recover the money.

Paul Simon

With a career spanning six decades, Paul Simon has been regarded as one of the best songwriters in music history. When he was just starting, Simon formed the duo Simon & Garfunkel, which released five studio albums. The two became one of the most praised groups of the 1960s. The singer was given credit for writing almost all their songs, such as The Boxer and Mrs. Robinson.

Simon was part of the group that was conned by known Ponzi schemer Kenneth Starr. The latter has already pleaded guilty to collecting millions from celebrity investors and is now awaiting sentencing. There is also very little chance that the celebrities would get any money back, considering that Starr only has about $140,000 in the bank, along with some artwork. The prosecutors are doing their best to seize Starr’s financial and real estate assets. We hope that this works out for the best, though.

Uma Thurman

Appearing on the cover of Vogue magazine back in 1985 and 1986 helped push Uma Thurman’s career forward. Following this, she was cast on her breakthrough role, Dangerous Liaisons, in 1988. She then became an established leading lady in Hollywood, with many notable films reaching blockbuster status. Some of these movies are Les Misérables, Percy Jackson & the Olympians: The Lightning Thief, and Batman & Robin.

One sad event, however, was that Uma Thurman became the main target of his financial advisor and money manager, Kenneth Starr’s Ponzi scheme. She claimed that $1 million was taken from her in a $30 million fraudulent scheme, which resulted in Starr admitting to the charges and was eventually put on trial.  It was good that Thurman was able to detect the scam and filed the appropriate charges, even though it was probably all to naught as Starr did not have money anymore.

Liza Minelli

Known for hits like the musical movie Cabaret, Arthur, and many other hit albums, Liza Minelli has proven herself a total celebrity. She can even act on both TV and film, and her alto voice is something the audience loves. Seeking to enhance her theatrical work, Minelli contacted the moving company to get her to New York in 1961. This decision started her career as a music performer, traditional pop artist, and musical theater artist.

Sadly, Minelli also fell victim to the scam perpetrated by Kenneth Starr, who targeted old and mostly retired celebrities for his Ponzi scheme. Fortunately, Starr faced the law and now has to be penalized for 10 to 20 years. Minelli might have to swallow the loss because it is unlikely her money would be recovered. We just hope that she remains financially solid despite this particular setback.


As a singer, it is without a doubt that Bono is very passionate. When he formed U2 in 1976, he was looking forward to a successful career, which turned out to be the case. His songs that are usually riddled with various themes, struck a chord with his audience. As the band grew, their songs took a more personal tone, reflecting their experiences.

Bono has made a series of good financial decisions in the past, but one that did not end so well was when he started Edun, an eco-friendly brand, in 2009. LVMH also invested in the brand, but it later turned red. LVMH then pulled out, making the brand sink a degree further. Edun has undergone rehabilitation, but as of 2018, it remained in the red. Bono has moved on and put some money on Facebook, which proved to be a wise move.


One of the most significant singers in pop culture, Madonna is otherwise referred to as the “Queen of Pop.” She rightfully deserves the title because, over the years, she has been noted for reinventing her music production, visual presentation, and songwriting. The singer has pushed the limits of her abilities and experimented with various music styles as well. Many celebrities also say that Madonna has influenced them to pursue a career in music.

One skill Madonna may have to brush up on relates to money management, as records show that she lost over $1 million after an internet company, ArtistDirect, did not deliver on its promise. The firm has suffered sustainable losses nearing $250 million over the last decades that it could not recuperate. What is good is that Madonna has other ventures that have been profitable such as Vita Coco, a coconut water company.

Wesley Snipes

Forming a company, Amen-Ra Films, in 1991 proved that Wesley Snipes could run a business. Solidifying his love for Egyptian names and symbols, he also established a security firm called the Royal Guard of Amen-Ra, the human version of a home security system for VIPs. All these business ventures were on top of his acting projects that included The Waterdance and Blade. Snipes also appeared on a couple of music videos, alongside Michael Jackson.

One aspect of business management that the actor forgot, however, was ensuring proper and timely tax payments. When the IRS audited him, they found some anomalies. He had been earning and accumulating more than $38 million in the bank since 1999 but only started filing taxes in 2006. He was eventually penalized for it, but we hope that Snipes would be more diligent with taxes once he starts over.

Kevin Bacon and Kyra Sedgwick

This power couple is two of the most influential people in Hollywood. Kevin Bacon has even been named one of the best actors who has never won an Academy Award. That may be the case, but his films have mostly turned out to be blockbusters. Kyra Sedgwick, whom Bacon has been married to since 1988, is an equally excellent actress, with a Golden Globe to her name. She is also noteworthy for her role as Madeline Wuntch on Brooklyn Nine-Nine.

The two, however, suffered adverse financial losses when they fell into the schemes of financial advisor Bernie Madoff who ran the biggest Ponzi scheme in North American history. Losing part of their savings was a big setback, but they found justice when Madoff was eventually arrested. Bacon and Sedgwick also saw through many positive things and focused on their children, health, and home as a way of coping.

Julius Erving

If there is anything Julius Erving is famous for, it is helping legitimize the American Basketball Association before it merged with the National Basketball Association. He won three championships, and as a result, he was inducted into the Basketball Hall of Fame in 1993. Sports Illustrated also named him one of the 40 most significant athletes of all time.

While Dr. J was a tough competition in the court, it was not the case when it comes to making financial moves. He fulfilled his dreams of owning a golf course back in 2007. The money he put in with the Heritage Golf Club, $3 million, came with a mortgage in default, resulting in Erving losing $5 million. He never took a paycheck as the club’s owner, but still, it resulted in the red. For sure, Erving is now much more careful when investing his money.

Nicolas Cage

The Ghost Rider actor has made himself quite popular and in demand. Nicolas Cage has appeared in various films that showcased his talents as an actor, and some of these projects include Honeymoon in Vegas, City of Angels, and Spider-Man: Into the Spider-Verse. He is also an avid comic fan, and at one point, he auctioned off $1.6 million worth of comics. Cage has also written comic book introductions for Juxtapoz.

Over the years, Cage has made some financial decisions that proved to be not so ideal. One investment he made was the purchase of a haunted house in 2006 for $3.45 million. It once belonged to Madame LaLaurie, and rumor said the house was home to ghosts. It was so unclear what he wanted to do with this, but it certainly was not for profit. He also bought a crocodile, which, if not illegal, might just be inappropriate.

Toni Braxton

Given credit for being one of the highest-selling R&B artists of all time, Toni Braxton certainly has amassed a significant amount in the bank. This fortune came mainly from being part of The Braxtons and selling over 40 million albums since they started in the 1980s. She also ventured into reality TV shows and producing, which helped solidify her fame even more. Her various accolades, from her seven Grammy Awards to her nine Billboard Music Awards, all point to an admirable career.

Braxton, however, ran into some financial issues both in 1998 and 2010. A series of wrong moves led to this, including problems with her health. It goes to show that investing in one’s health is critical. Fortunately enough, she made a career renaissance, which eased her financial burdens. Just recently, in 2020, Braxton released Spell My Name, her tenth studio album. Well, she should not lose hope just yet!

Shaquille O’Neal

The 1992 Draft opened the floodgates for Shaquille O’Neal as this allowed him to be among the best basketball players of all time. During his 19-year career in professional basketball, the player has become part of six teams. When he was a free agent with the Los Angeles Lakers, he led them to victory three times, in 2000, 2001, and 2002. O’Neal had also proven himself to be business savvy when he went on to buy a minority share in the Sacramento Kings.

Not all of his financial moves were profitable, though. He made poor investments in an unnamed paper company. The basketball legend was promised profits, which never materialized. This event was apparently not the first because he revealed that when he was younger, he was also prone to scams. Maybe this experience will now help him get better at identifying legitimate business deals and bogus ones.

Arnold Schwarzenegger

It’s safe to say just about everyone can recognize Arnold Schwarzenegger. Before beginning his career under the spotlight, Schwarzenegger garnered a skyrocketing degree of recognition for his work in the bodybuilding scene, having won seven Mr. Olympia contests throughout that time.

Although he is still a relevant figure in the bodybuilding community, Schwarzenegger has since become most known for his roles in films, including PredatorThe Terminator franchise, Total Recall, and Conan the Barbarian— the latter being his breakthrough role. With Bruce Willis, Demi Moore, and Sylvester Stallone, Schwarzenegger also invested in the Planet Hollywood chain of restaurants. Besides that, he also opened his own restaurant called Schatzi On Main. Sadly, after a couple of years, he ended his involvement on both projects, severing his financial ties with Planet Hollywood around 2000 and selling Schatzi On Main two years prior.

Britney Spears

The music scene has introduced us to numerous famous figures since its inception, and that includes Britney Spears. At a young age, Spears already knew her way around dancing and singing, debuting on her kindergarten graduation with a performance of What Child Is This. She then had the chance to appear in a couple of TV shows, but her first shot to fame came when she starred in The Mickey Mouse Club.

Since then, Spears has become one of the industry’s best-selling artists, selling over a hundred million records around the world. Along with this achievement, though, the singer has also encountered a couple of hurdles through the years, one of which is her investment in a New York City restaurant called Nyla. Due to a couple of changes, the project barely lasted a year before Spears finally closed it down.

Bruce Willis

Since the beginning, Hollywood has shone its spotlight on numerous celebrities, one of whom is Bruce Willis. Throughout his childhood, Willis had a hard time dealing with his stutter. Even so, he eventually overcame the problem when he started acting on stage plays. After his time in school, he began his acting career performing on stage productions, and not long after, he landed more on-screen roles in movies.

After landing his breakthrough role in the TV series Moonlighting, Willis eventually became most known for his acting credits in movies such as the Die Hard franchise and The Sixth Sense. The actor has also dabbled in real estate, with his most notorious venture being in the town of Hailey, Idaho. Although it was initially quite a successful move, the actor suddenly called off his work in the town. Among the establishments he launched there included a movie theater, a bar, and a restaurant.

Burt Reynolds

More often than not, starting a journey can be quite challenging on its own. Most of the time, we would need some sort of push to help us keep our feet on the gas pedal. Well, for Burt Reynolds, that metaphorical push came in the form of his college English teacher, who gave him a lead role in his stage production of Outward Bound.

With a career spanning almost six decades, Reynolds has become famous for his roles in The Longest YardGunsmokeEvening Shade, and Smokey and the Bandit. Like his celebrity colleagues, the Deliverance star also dabbled in other ventures, some of which, sadly, weren’t as successful as the others. This endeavor, of course, includes his stint in the restaurant business, where he invested in two chains that ultimately cost him more than what he earned. By the looks of it, though, his subsequent projects helped him back to his feet.

Curt Schilling

Like most of his peers, Curt Schilling began his journey into baseball during his high school years, followed by his run in the college baseball scene. Soon after, he finally made his way into the big leagues in the MLB. Throughout his near-20-year stint, Schilling had the chance to play alongside the Houston Astros, Philadelphia Phillies, and the Boston Red Sox, the last team he played with before retiring.

Besides his passion for baseball, Schilling also surprisingly has a high degree of love for board games and video games. With the fortune he earned along the way, it comes as no surprise he eventually started his very own video game company called 38 Studios. Although this was undoubtedly an endeavor made out of Schilling’s fondness for gaming, the studio only released one game, titled Kingdoms of Amalur: Reckoning, before it sadly closed its doors for good due to financial reasons.

Debbie Reynolds

Being around at the right place at the right moment can sometimes do wonders. Such was the case for Debbie Reynolds. At 16 years old, she had the chance to join the Miss Burbank beauty contest. Not only did she win, but she also got the attention of one Warner Bros. talent scout, and her journey into the spotlight began soon after.

With a career spanning almost seven decades, Reynolds has become most known for her acting credits in films such as Singin’ in the RainTammy, and Three Little Words, the latter being her breakout role. Besides acting, the Unsinkable Molly Brown star also ventured into other businesses. She experienced success and encountered a couple of not-so-fruitful projects, the most notable being her Debbie Reynolds Hollywood Hotel. Despite the setback, it didn’t stop her from continuing her career, which concluded with her 2016 documentary.

Demi Moore

For her start in the entertainment industry, Demi Moore began her career as a model for the Elite Modeling Agency. During this period, she also took drama classes. Not long after, she finally made her way into the acting scene, debuting with a minor role in the 1981 film Choices. Since then, Moore has become remarkable for her work in titles such as A Few Good MenSt. Elmo’s Fire, and Charlie’s Angels: Full Throttle.

During her relationship with actor Bruce Willis, the Disclosure actress contributed a portion of her investment money in creating a few establishments in the town of Hailey, Idaho. As mentioned earlier, their redesigned Liberty cinema and Mint bar/restaurant helped bring the town back on the map. Numerous tourists, locals, and even celebrities went and enjoyed these attractions, making it all the more a shame that it all ended on a very sour note.

Flavor Flav

At a young age, William Jonathan Drayton Jr. already had a high degree of love for music. In fact, at just five years old, he already knew his way around the piano. Now he can play 15 instruments, including guitar, piano, and drums. Thanks to his talents, he eventually found his way into the rap scene, where he donned his stage name, Flavor Flav.

Besides being a solo artist, Flav is also part of the rap group Public Enemy, which he co-founded with long-time partner Chuck D. Along the way, the rapper also dabbled in a couple of other endeavors, including his stint on shows such as The Surreal Life and The Farm. Even so, the rapper is also no stranger to failed ventures, with the most known one arguably being his Flav’s Fried Chicken chain of restaurants, which only lasted around four months before its unfortunate closing.


Another rapper who has garnered widespread fame and success under the spotlight is Shawn Corey Carter, who is widely recognized under his stage name, Jay-Z. After receiving a boombox for his birthday, he began composing his own lyrics and even worked on his freestyling skills. Well, with the gift of retrospect, it’s safe to say these hobbies turned out to be investments he will never regret making in the future.

Besides his music career, Jay-Z is also regarded for his numerous successful ventures, including his 40/40 Club chain of luxury sports bars and the Rocawear clothing retailer. Even so, this doesn’t mean he isn’t immune to a couple of bumps along the way, which includes his failed project of turning a former Time Warner Cable warehouse into a hotel. It was called J Hotels. On the bright side, though, this setback didn’t stop him even for a moment from accumulating an impressive net worth of $1.4 billion.

Kanye West

Even during his childhood, Kanye West already had quite a fondness for music. Not only did he enjoy listening to his favorite tunes, but he also already showed a knack for composing a few beats of his own. Noticing this, his mother then helped him get one of his works recorded. Well, from that point onward, he has achieved even higher degrees of success since then.

Today, West is one of the music industry’s most recognized and best-selling artists, thanks to his widely-acclaimed albums like My Beautiful Dark Twisted FantasyGraduation, and Ye. Besides this, the rapper-singer is also famous for his ventures in the fashion side of things. He may be known for his Yeezy line of shoes nowadays, but this wasn’t his first attempt in the business. The first one was called Pastelle Clothing, which was stuck in development for four years before it was sadly canceled.

Kim Basinger

For most of her childhood, Kim Basinger considered herself quite a shy person but eventually became more confident with herself during her mid-teens. For this, perhaps a portion of the credit goes to her time learning ballet.

After her five-year stint in the modeling business, Basinger mostly had guest appearances in shows such as Charlie’s Angels and McMillan & Wife before landing her debut starring role in Katie. Since then, the actress has had a fruitful run under the spotlight. With the wealth she earned, however, the actress did something unusual, even among her colleagues. She purchased a hefty portion of the town of Braselton, Georgia – about 1,751 acres out of its 2,000-acre plot of land. Despite hoping for it to become a venue for art shows and film festivals, the plans didn’t push through, and the property was eventually sold once again.

Mark Twain

At this point, plenty of booklovers have at least heard of Mark Twain. Born Samuel Langhorne Clemens, “Mark Twain” being a pen name, he spent most of his childhood working as a typesetter and printer. For his studies, he would spend most of his nights in public libraries reading books.

Since then, the author is best known for his novel The Adventure of Tom Sawyer and its sequel Adventures of Huckleberry Finn. Well, with all the fortune he’s earned along the way, it’s no surprise Twain spent a portion of his investment money on a couple of ventures that included the Paige Compositor, a typewriter of sorts. Unfortunately, it ended up becoming a failure due to it not faring well against its competitor, the Linotype. Good thing his subsequent literary pieces and lectures helped him recover from this financial setback.

Steven Spielberg

When talking about world-famous filmmakers, it would be a disservice not to give credit to Steven Spielberg and his contribution to the industry. At a young age, he already began making his own homemade films, and by the looks of it, this hobby helped him develop the skill he has since become most known for.

Nowadays, Spielberg is widely regarded for creating films such as JawsET the Extra-TerrestrialSaving Private Ryan, and Jurassic Park. Along the way, he has also worked on other endeavors, one of which is the creation of the Medal of Honor videogame series. With that said, another project he did was the submarine-themed restaurant called Dive, which attracted numerous visitors during its earlier years. Even so, the filmmaker’s reputation and the venue’s unique approach to things weren’t enough to keep the business. It led to its unfortunate closing by 1999.

Sylvester Stallone

Of course, whenever Arnold Schwarzenegger is involved, rest assured that Sylvester Stallone won’t be too far behind. After all, they are both well-known for being two of Hollywood’s iconic action stars. Like many of his peers, however, Stallone’s start in the industry was far from easy. After some time landing only minor roles, the then-aspiring actor finally found his big break as the titular boxer in the Rocky films.

Since then, Stallone has landed an acting credit in other notable projects such as the Rambo movies, Demolition Man, and The Expendables films— the latter letting him star alongside long-time colleague and good friend, Schwarzenegger. Besides The Expendables, the two also worked together on the previously-mentioned restaurant chain, Planet Hollywood. Throughout their time backing the establishment, over 100 locations were made. Although they have since parted ways with it, Planet Hollywood is still in business under a different owner, with branches around New York City, London, Las Vegas, and Paris.

The Kardashian Sisters

Aside from the scripted shows and movies we watch, producers in the entertainment industry have also released plenty of reality shows, which revolve around the daily lives of a certain group of people. With that said, one popular title would be Keeping Up with the Kardashians, a show that focuses on the now-famous Kardashian-Jenner family.

Outside their work on the show, these reality stars are also known for spending their investment money on several ventures, most notably in the fashion scene. Along the way, the Kardashian siblings decided on another seemingly interesting tie-in product. Well, the product in question was the Kardashian Kard, a Keeping Up with the Kardashians-themed debit card they made in partnership with the University National Bank. This endeavor instantly caused quite a buzz which eventually led to its discontinuation. Its 250 consumers were given 30 days before the card was declared unusable.

Cindy Crawford & Randy Gerber

Cindy Crawford is a well-known American actress, model, and businesswoman. She began dating businessman Rande Gerber for several years until they tied the knot in May 1998. Considering that they’re both incredibly influential figures in Hollywood, they dealt with their fair share of troubles.

The biggest issue that the couple probably has ever dealt with was when a model named Edis Kayalar attempted to milk $100K out of them. Kayalar reportedly showed them a photo of their beloved daughter, all tied up. Soon it was revealed that the person who took the photo was their daughter’s nanny, who was dating the model. Kayalar was later extradited to the US on extortion charges. Though Crawford and Gerber lost $100K, we’re confident that it was a small price to pay for their daughter’s safety and that they didn’t even need loans to come up with the money.

Liv Tyler

Liv Tyler is a popular American actress who has appeared in several films. Some of her notable appearances are in blockbusters like the Lord of the Rings trilogy, Silent Fall, and Inventing the Abbotts. Besides acting, Tyler is also a successful producer, model, and singer. Without a doubt, she’s an exceptional multi-talented figure in Hollywood.

Interestingly, she was also a victim of certain dishonest schemes. The only difference in her case is that she didn’t get conned by her financial advisor or manager. She experienced a dishonest scheme through her dermatologist named Mari Gabriela Hashemipour. Hashemipour was supposedly a renowned skin expert who has already worked with prominent names like Jennifer Aniston and Cher. However, she had more intentions than just taking care of her celebrity client’s skin. She also took Tyler’s card details and used them on her own personal shopping spree.

Ben Stiller

Almost everyone on this planet knows who Ben Stiller is. He’s a successful actor who has appeared in countless films throughout his career. His success in Hollywood seems to be premeditated as he inherited the talents of his mother and father, who were also famous actors. Outside of acting, Stiller is also a producer, comedian, director, and screenwriter, and he has been able to win several awards throughout his career.

Considering his fame, Stiller is also a magnet for people with bad intentions. He once asked his financial advisor named Dana Giachetto, to take care of and oversee his finances. Unfortunately, Giachetto wanted to take advantage of his wealth and pocketed $250K for himself. Giachetto was also found to be pocketing money from his other clients worth over $10 million. Of course, he was found guilty and was ordered to serve three years in a correctional facility.

Kiefer Sutherland

Kiefer Sutherland is one of the most recognizable actors on television. He’s best known for his award-winning acting credit in the long-running drama series 24. Besides his illustrious television career, Sutherland also managed to star in films like Stand by Me, Young Guns, Flatliners, and many more. Moreover, he earned numerous accolades, including the induction to Hollywood’s Walk of Fame and a Lifetime Achievement Award at the Zurich Film Festival.

Sutherland may look like the most brutal anti-terrorist cop in 24. It sure looked like he can deal with any problem in order to save the world. His on-screen persona and reputation, however, didn’t stop Michael Wayne Carr to swindle $869K from him. Carr was able to convince the actor to put his money into selling steers. It turned out that the swindler was never into the steers business in the first place, and he’s now facing numerous felony charges.


Sting is undeniably one of the most successful musicians of all time. He’s best known for being the lead singer, songwriter, and bassist for the iconic rock band the Police between 1977 until 1984. After his successful stint with the Police, Sting was able to carve a successful solo career, and he has ventured and found success in mixing rock, reggae, jazz, and many other genres in his music. He’s also incredibly wealthy as he sits on a fortune of $400 million.

Sting was also a victim of fraud coming from his financial advisor. At the time, he was unable to notice that Keith Moore was already pocketing his money. Sting hired Moore to handle his portfolio and to take care of his money. Unfortunately, Moore didn’t take care of his finances at all as he used his money to invest in various deals and satisfy his other financial cravings.

Elton John


Elton John is an iconic musician who has enjoyed a massively successful music career. He was able to sell over 300 million records worldwide, and currently ranks as the fifth best-selling musical artist in history, just behind Michael Jackson, Madonna, Elvis, and the Beatles. John continues to bring in millions to this day as he earned $85 million in just 2018 and 2019!

Many people know John to be a big spender. It’s incredibly shocking that he also lost a whopping $29 million due to financial mismanagement. The singer-songwriter then sought the counsel of his lawyer and sued his management agency, comprised of Andrew Haydon, and the accountancy firm PricewaterhouseCoopers. He moved forward with the case with hopes of being able to retrieve his money, but sadly, the lack of evidence paved the way for the case to be dismissed.

Robert de Niro

Speaking of iconic Hollywood personalities, Robert de Niro is one of them. He’s best known for starring in nine motion picture films with renowned filmmaker Martin Scorsese. Besides a career filled with coveted acting credits, de Niro also received several accolades, including a Screen Actors Guild Life Achievement Award.

De Niro is also known for exuding a tough-guy persona, both on-screen and in his personal life. It’s quite a surprise that someone would ever have the guts to try and con this legend. Interestingly, a man named Lawrence Salander gutted it out and swindled the actor $88 million. De Niro is a well-known art enthusiast who decided to sell 50 artworks with Salander as the middleman. The artworks sold for a ton of money, but Salander didn’t give the Hollywood star his money. Instead, he used it to pay off all of his debts.

Billy Joel

Billy Joel is a legendary composer and singer-songwriter. He has released several albums and singles throughout his career and has been a successful solo act since the 1970s. Joel sold over 150 million records worldwide. If there’s a list of best-selling music artists of all time, his name would certainly appear on top.

Despite his success, Joel experienced several financial turmoil throughout his career. One can argue that the most excruciating money trouble he has ever experienced was when he lost over $90 million to his former brother-in-law, who also acted as his one-time manager. His name was Frank Weber, and he fraudulently took $90 million from the musician and used it to fuel several investments that made him wealthy. The music legend filed a series of lawsuits against his former manager but was only able to get $8 million back.

Antoine Winfield

Antoine Winfield was once the top-ranked defensive back in the country. He was a sure-fire first-round pick out of the Ohio State University. The standout defender, however, couldn’t properly manage his finances, which led to him allowing almost half of his $3.5 million signing bonus to go down the drain. What’s even more disturbing is that he could have easily avoided this scenario from happening.

The man responsible for Winfield’s huge financial loss was his close friend and adviser, Dunyasha Mon Yetts. Yetts allegedly promised him that he would use the money in various investments that would work well for him in return. In reality, Yetts pocketed some money into his own bank accounts. All of this was actually done in good faith from Winfield, who believed that his close friend was busy investing the funds for a healthy financial gain.

Art Monk

Art Monk is another prolific NFL player who also lost money due to fraudulent investments. As an NFL player, Monk is the first player to have caught a touchdown pass in 15 consecutive seasons. He’s undoubtedly an all-time great receiver who had an illustrious sports career. Unfortunately, he’s also one who fell victim to deception through a business venture by an unlikely foe.

You certainly won’t expect someone to lose money through a teammate. For Monk, he lent his former teammate Terry Orr some money to invest in Orr’s shoe company. Orr also took money from other teammates and reportedly received $50,000 from them, having been interested in his start-up business. Unfortunately, he used the money and paid off his personal debts instead. He was found guilty and sentenced to serve in a correctional facility. It’s sad to say Monk’s money was nowhere to be found.

Darren McCarty

Darren McCarty is a retired Canadian ice hockey player who is best known for his years playing for the Detroit Red Wings, for which he won four Stanley Cups. He played as the enforcer for most of his career, and he was known to be a physical player on the ice. Despite his presence and toughness on the ice, McCarty wasn’t completely invincible from fraudulent business transactions.

He lost money through his business partner, who took out a $3 million personal loanin his name. His partner allegedly took it out of McCarty’s personal savings account and even went as far as forging his name on a $650,000 check. It’s certainly troubling that the athlete experienced this from his business partner, whom he must have really trusted. Nonetheless, it’s an unfortunate situation as the amount that is in question here is certainly no chump change!

Deuce McAllister

Every Louisiana native has an idea about Deuce McAllister. He was a prolific NFL player who played running back for the New Orleans Saints for eight seasons. McAllister was also selected into two Pro Bowls in his career and was a part of the New Orleans Saints squad that won the 2009 Super Bowl XLIV. Unfortunately, his illustrious career didn’t translate well into his retirement, as he lost a ton of money after he stepped away from football.

After his playing days, McAllister owned a Nissan dealership located in Mississippi. Unfortunately, his post-football business investment didn’t exactly go as planned, nor was it as flourishing as his football career. He reportedly owes Nissan around $930,000, and his inventory was trucked away by an eighteen-wheeler truck. The dealership went out of business, and we’re hearing that they’re also facing $5 million in lawsuits.

Eric Dickerson

Eric Dickerson is certainly a household name when it comes to football success. He was a star running back who is best known for his trademark prescription goggles. Dickerson rushed for over 13,000 yards, and he still holds the NFL’s single-season rushing record to this day.

Everything about the football pro seems to be related to speed. He was also the fastest one to believe that his financial advisor was an Italian Count. His name was Luigi DiFonzo, and he and Dickerson met during a Hall of Fame dinner in Canton, Ohio. The athlete must’ve been intrigued by DiFonzo’s business proposition as he decided to invest his money with DFJ Italia soon afterward. What he didn’t know was that DiFonzo was a two-time felon. He was a con man who targeted NFL players, and unfortunately, Dickerson was one of the victims who fell into his trap!

Fred Taylor

Fred Taylor is an NFL running back who, unfortunately, ended up on our list. He played in the NFL for 13 seasons and enjoyed an outstanding sports career. He played for the Jacksonville Jaguars and the New England Patriots, and he’s a member of the 10,000-yard rushing club, an exclusive club for running backs who were able to rush over 10K yards.

Taylor’s NFL career may be overshadowed by one thing off the field. He invested his money with renowned agent William “Tank” Black. It’s worth noting that Black represented other famous athletes like Vince Carter and Sterling Sharpe. The running back must have liked Black’s investment and business proposition for him to invest his entire $5 million signing bonus as a rookie. Black would end up facing numerous felony charges. Taylor’s money, on the other hand, has gone adrift.

John Elway

John Elway is a football player who is widely considered one of the greatest quarterbacks in history. Elway led the Denver Broncos to two Super Bowl championships in 1998 and 1999. In turn, it was a no-brainer for the Broncos to pay him a large sum of money.

Elway earned hundreds of millions in his days as a professional NFL quarterback. He was a Superbowl MVP, and he was known to have thrown up accurate Hail Mary passes in his day. Who would have thought that he’d throw up a sizable hedge fund investment once he retired? He and a business partner committed a whopping $15 million to hedge fund manager Sean Mueller. Regrettably, Mueller’s hedge fund turned out to be a Ponzi scheme. Anyway, Elway still sits on a fortune worth $145 million, but the hedge fund was certainly one business decision he’d like to take back.

Johnny Unitas

Following a professional American football career that spanned from 1955 to 1973, Johnny Unitas was consistently listed as one of the greatest players of the National Football League of all time. He primarily played with the Baltimore Colts as quarterback for eighteen seasons. In 1959, 1964, and 1967, Unitas was named the Most Valuable Player. Additionally, the footballer received ten Pro Bowl and first-team All-Pro honors.

Unitas led the Baltimore Colts to their four championship titles, three of which were in the pre-merger era in 1958, 1959, and 1968. He also led the team to a Super Bowl V championship title during the Super Bowl era. After he retired from the sport, Unitas ventured into several business investments, including real estate, restaurants, bowling alleys, and broadcast booth. Unfortunately, his circuit board company did not do well, forcing him to sell off the company’s assets.

Lenny Dykstra

Lenny Dykstra played for Major League Baseball as a center fielder from 1985 to 1989 for the New York Mets and from 1989 to 1996 with the Philadelphia Phillies. He won a World Series championship with the Mets and a three-time All-Star. The batter began his professional baseball career in 1981 when he was picked as a thirteenth-round pick for the Mets. He was a star in the minor league in which he led the Carolina League in at-bats, stolen bases, batting, triples, hits, and runs.

At the age of 35, Dykstra retired and ventured into a number of business investments. Among his dealings were internet-related ventures and car wash operation, which enabled Dykstra’s net worth to grow. However, one of his businesses caused his financial downturn—his magazine company, The Players Club. It’s supposedly a lifestyle guide for wealthy professional athletes. Due to mishandled finances, the downfall of his success was inevitable.

Mark Brunell

Well known for playing with the Jacksonville Jaguars for nine seasons, Mark Brunell led the franchise’s first playoff appearances between 1996 and 1999. He played for nineteen seasons throughout his career in the National Football League. In 2013, Brunell was inducted into the Pride of Jaguars. Initially, in his career, he was drafted by the Green Bay Packers at the 1993 NFL Draft in the fifth round. Two seasons later, he was eventually traded to the Jaguars during their inaugural season in 1995.

In 2012, Brunell became an assistant football coach at the Providence School in Florida. As his net worth grew over the years, Brunell ventured into real estate investments together with his two former teammates, and they founded Champion LLC. Subsequently, the housing market collapsed, so he then invested in the popular burger chain Whataburger. Sadly, he ended up losing his funding as well.

Mike Pelfrey

Before becoming a professional baseball player, Mike Pelfrey played for the Wichita State University from 2003 to 2005 for Head Coach Gene Stephenson. In his junior year in college, he entered the amateur baseball draft in 2005, leading to his MLB career with the Minnesota Twins, Detroit Tigers, New York Mets, and Chicago White Sox.

In 2018, after his retirement from professional baseball, Pelfrey accepted a coaching job at Newman University. A year later, he became the pitching coach at Wichita State University. Over the years, the baseball coach accumulated a considerable amount of money in his career and used some of it as investment money.Along with other professional baseball players, he placed their funds in Stanford Financial, which was later discovered as a money scam. Unfortunately, they ended up losing much of their assets due to some issues of the company with the U.S. Government.

Raghib Ismail

Raghib Ismail came to prominence after playing college football for Notre Dame Fighting Irish. He then played in the Canadian Football League from 1991 to 1992 and in the National Football League from 1993 to 2001. Ismail was a CFL All-Star in 1991, and he set a record for two 1,000-yard receiving seasons in NFL, as well as the Most Valuable Player at the 79th Grey Cup. He was among the top 100 Greatest College Football Players of All Time, ranked 75th by the College Football News.

Sometime after he retired from professional football, Ismail ventured into several business investments. Among them was a “Rock and Roll” themed café, a record label called “COZ Records,” a calligraphy business, a souvenir shop, a movie, a line of cosmetic surgery supplies, and machines that dispensed prepaid phone cards. Sadly, none succeeded. Some factors that contributed to the downfall were lack of management oversight, like in his café.

Scottie Pippen

Along with Michael Jordan, Scottie Pippen played a significant role in transforming the Chicago Bulls into a championship team and popularizing the NBA worldwide in the 1990s. Pippen played for seventeen seasons in the league and won six NBA championships with the Chicago Bulls. He is acknowledged as one of the best small forwards of all time. He was also named NBA All-Defensive First Team eight consecutive times, All-NBA First Team thrice, NBA All-Star seven times, and NBA All-Star MVP.

Aside from his professional basketball career, the former basketball player also had investments in the past, which were unfavorable. One of them was his purchase of a Gulfstream jet with a price tag of $4 million from a company called Air Pip. Unfortunately, due to missed inspection, the jet’s engine needed repairs which cost up to a million dollars. The plane never got off the ground since its purchase.

Sheryl Swoopes

Sheryl Swoopes became the first Women’s National Basketball Association (WNBA) player to be signed in the league. She’s a three-time WNBA Most Valuable Player and was named one of the league’s top fifteen players of all time in 2011 during the WNBA All-Star game. Swoopes won three Olympic gold medals, making her one of the ten women’s basketball players who won a WNBA title, an Olympic gold medal, and an NCAA Championship title. In 2016, she was instated into the Naismith Memorial Basketball Hall of Fame.

Often dubbed as the “Michael Jordan” of WNBA, Swoopes went short in the business category compared to Mike. Though she had sponsorship deals like the Air Swoope, which became the first sneakers named after a woman, the WNBA player still couldn’t sustain her fortune. Because of poor decisions and money management, she ended up losing her wealth.

Terrell Davis

From 1995 to 2001, Terrell Davis played for the Denver Broncos of the National Football league as a running back. He set the record for the most touchdowns in a postseason single-season with eight touchdowns. Davis was also credited with starting the “Mile High Salute,” a celebratory tradition among Denver Broncos players, which was done after scoring a touchdown.

At the 1995 NFL Draft, Davis was chosen by the Denver Broncos in the sixth round as the 196th overall pick. He has set numerous franchise and NFL records as well. After his retirement, he worked as an NFL network’s correspondent and studio host for NFL Total Access. Davis later invested in a hedge fund with his growing financial asset, but it adversely affected him. It turned out that the fund manager had something unfavorable in his mind, causing Davis to lose his money.

Torii Hunter

Torii Hunter played professionally in Major League Baseball with the Los Angeles of Anaheim, Minnesota Twins, and Detroit Tigers between 1997 and 2015. He won Gold Glove Awards nine consecutive times as a center fielder, a five-time All-Star, and a two-time Silver Slugger Award winner. However, it was not until 1999 that he began to play regularly, playing 135 games for the Twins.

After decades of a successful baseball career, Hunter retired from the sport in October 2015. Back in the 2000s, the batsman had made some investmentsin an inflatable raft invention that would allow consumers to pump the raft in an event where flood is imminent. Initially, he shelled out $70,000 for it, but the inventor wanted him to invest more despite not having any product to show. Luckily, the batter came to his senses and avoided a potential loss of up to $500,000. s

Travis Henry

At the 2001 NFL Draft, Travis Henry was drafted by the Buffalo Bills in the second round, and he went on to play for other teams such as the Denver Broncos and Tennessee Titans. He played as a running back in the National Football League for seven seasons throughout his career. In his high school years, he was credited as “Mr. Florida Football” and All-American by the news magazine Parade while playing as a running back at Frostproof Middle-Senior High School.

Henry was traded to the Tennessee Titans in 2005, and eventually, to the Denver Broncos. In his professional career, he became the fourth-leading rusher in Buffalo Bills’ franchise history with 27 touchdowns and 3,849 yards with 4.0 yards per carrying average. Henry had a great NFL career in front of him, but with one wrong decision concerning his personal life, everything slipped through his fingers.

M.C. Hammer

M.C. Hammer became prominent and commercially successful in his music profession as a singer, dancer, record producer, and rapper from the late 1980s to the late 1990s. He is best known for songs such as U Can’t Touch This and 2 Legit 2 Quit, dance choreography, and eponymous Hammer pants. Hammer is also known as the pioneer and innovator of pop-rap, as well as the first artist ever to achieve diamond status for an album.

Eventually, Hammer transitioned into a preacher in the late 1990s with a ministry program called M.C. Hammer and Friends on TBN. In his career in the entertainment scene, the singer-rapper achieved considerable success. However, he mismanaged his wealth, spending all his fortune by purchasing lavish luxuries, such as jets, mansions, an entourage of 200 people, racehorses, and many more. Luckily, he was able to bounce back by investing in tech companies— credit to his resilience.

Terrell Owens

A six-time Pro Bowl selection, Terrell Owens played for sixteen seasons in the National Football League as a wide receiver. He is a five-time first-team All-Pro and holds several NFL records. He ranked third in receiving touchdowns at 153 and third in career receiving yards at 15,934. After playing for the University of Tennessee at Chattanooga, Owens was selected by the San Francisco 49ers at the 1996 NFL Draft in the third round. He played for seven seasons with the 49ers and got traded to the Philadelphia Eagles in 2004.

Two years after, Owens signed with the Dallas Cowboys and was eventually released the following three seasons. Over the years, he achieved great success in his profession, and his wealth grew as well. However, he did some bad investment planning, like his casino venture that went bust. His real estate portfolio was greatly affected when the housing market collapsed.

50 Cent

Known for his substantial impact in the hip hop industry, American singer, television producer, rapper, and entrepreneur 50 Cent has been described as a “master of the art of lyrical brevity.” In 2000, he began his music career and produced Power of the Dollar for Columbia Records. He then released the compilation album Guess Who’s Back? Discovered by Eminem, 50 Cent was signed to Shady Records under the support of Dr. Dre’s Interscope Records and Aftermath Entertainment.

He became one of the best-selling artists globally with the aid of Dr. Dre and Eminem, who produced his major-label album Get Rich or Die Tryin. As of 2021, the famed rapper is working on his sixth album, Street King Immortal. As his net worth grew, 50 Cent made some poor investments in real estate, financial market, boxing promotions, fragrances, vodkas, and many others, which ultimately plummeted his fortune.

Ed McMahon

Ed McMahon began his television series and association with Johnny Carson on ABC network’s game show Who Do You Trust?, which ran from 1957 to 1962. He then made his famous thirty-year mark as Carson’s announcer, sidekick, and second banana on The Tonight Show Starring Johnny Carson on NBC, from 1962 to 1992. From 1983 to 1995, McMahon hosted the original Star Search. He also anchored the team of NBC personalities of the Macy’s Thanksgiving Day Parade during the 1970s and 1980s.

Aside from his hosting job, McMahon also appeared in several films such as Full Moon High, The Incident, Fun With Dick and Jane, and Butterfly. As his fortune grew, his wife encouraged him to venture into some investments, such as diet pills, luxury clothing, a vodka company, and real estate properties. Sadly, all ventures didn’t go well as planned.

Dorothy Hamill

Dorothy Hamill is a retired figure skater who grabbed both the World Figure Skating and Olympic championship in 1976. In 1983, she was awarded a prestigious Emmy trophy for her outstanding individual achievement in the world of the performing arts. Hamill is also an inductee at the World Figure Skating Hall of Fame since 2000, and a skating rink in her hometown in Greenwich, Connecticut, is even named after her. She is married to John MacColl since 2009.

Her time with Ice Capades, a touring theatrical ice skating show, surely earned a special place in her heart that she chose to spend her riches for this company. Yes, it was in 1993 when she decided to drop her investment money to acquire it. However, the masses reportedly lost admiration for the Ice Capades, which forced her to sell it two years after the acquisition.

Ted Nugent

Ted Nugent is a guitarist, singer-songwriter, and activist. He became famous after he joined the band The Amboy Dukes, where he played as the lead guitarist. However, he eventually left the group in 1975 to pursue a solo career and scored a deal with Epic Records. He then released multi-platinum albums, including Ted NugentCat Scratch Fever, and Free-for-All. These records house several radio anthems such as Stranglehold, Hey Baby, and Dog Eat Dog.

Nugent’s popularity has caused him to fill every seat in most of his shows in the U.S., and it surely improved his credit score. His managers invested his wealth in businesses that were deteriorating, one of which was a mink farm. In 1980, these bad judgments resulted in him losing his money.  He must have learned by now to choose the right people to trust, especially with his finances.