What Does a Financial Comeback Really Look Like?

What Does a Financial Comeback Really Look Like?

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There really is nothing quite like a good comeback story. As a culture, we’re enraptured by tales of individuals, businesses, families, and even sports teams recovering from a low point only to come out on top at the end of it all. We like to look at these comeback stories for inspiration and renewed hope that we can overcome our own problems.

When it comes to money problems, hearing about what it’s like to bounce back from a financial low can be very empowering. Take a look at these celebrities who went bankrupt and their stories of recovery. A financial comeback isn’t like a double-rainbow — that is to say, it doesn’t have to be a rare occurrence.

Anyone can bounce back from financial troubles; you just need the right help. A credit counselling firm like ours, staffed with knowledgeable and empathetic Licensed Insolvency Trustees (formerly known as bankruptcy trustees), credit counsellors, and debt management professionals is one place to start.

Hopefully, the following celebrity tales can remind us that everyone is human and might come across money troubles that require government-regulated methods of recovery. Let’s take a look.

Celebrities Who Went Bankrupt

It’s no secret that celebrities really are just like us. They suffer heartbreak, health issues, and they have their happy moments and pitfalls, too. Wealth and fame might go hand in hand, but that doesn’t mean that those who are famous are always wealthy.

Sometimes a celebrity hits a rough patch (just like regular people) and winds up in a tough financial spot. For everyone else, it can be shocking to see just how much money these celebrities can misspend, which is why we’re so often interested in stories about how the mighty have fallen.

Celebrities who experienced bankruptcy or serious financial lows are shining examples of what it can look like to bounce back from money troubles. Take a look at the following celebrities and the ways that they handled some of their darkest moments. At David Sklar & Associates we are ready to help individuals and businesses who are facing insolvency. Whether your situation is similar to these celebrity tales or completely unique to you and your life, we can offer you the help you need.

50 Cent

The rapper with the stage name that’s less than a dollar, 50 Cent earned a reputation for himself as a canny businessman. He amassed $300 million in just a few years thanks to more than just music (an early investment in Vitaminwater reportedly paid off big time).

The public was a little confused, however when the rapper declared bankruptcy in 2015. Despite having an estimated net worth of a half-billion dollars, the rapper declared bankruptcy in 2015, claiming to be more than $20 million in the hole — while at the same time posting images on social media featuring him posing with stacks of $100 bills spelling out the word “broke” (his lawyers insisted the cash was actually “prop money.” He was discharged in 2017, paying off $22 million in debt.

Kim Basinger

Do you take financial advice from family? It’s a touchy subject, money and family, since the two have been known to collide in nasty ways, especially for those in the public eye. Such was the case of Kim Basinger, who, on the questionable advice of family members, bought an entire town in Georgia (all 1,700 acres of it) for the price of $20 million.

Her plan? To turn the place into a tourist attraction by building a movie studio and establishing a film festival. Those plans never came to fruition, however, since Basinger later ran into some financial difficulties that forced her to sell off big chunks of the place. Down the line, she later admitted that “nothing good came out of (the purchase),” since the entire experience reportedly caused a major a rift with her family.

Then came the 1993 film Boxing Helena, which Basinger first agreed to do but then backed out of after taking a closer look. Since Hollywood execs are known to be anything but lenient, the movie studio took her to court and won after she backed out of the project.

Basinger was ordered to pay a judgement of $8.1 million. This led Basinger to file for bankruptcy; she subsequently appealed the decision to a higher court, which ruled in her favour, and she later settled with the studio for $3.8 million.

Marvin Gaye

Known for his publicly difficult life, Marvin Gaye definitely experienced his share of tough times. His music, however, still holds up and Gaye is today known as a soul legend. He achieved popularity thanks to his hits like “What’s Going On,” and “Heard It Through the Grapevine,” but that wasn’t enough to keep the musician and singer from declaring bankruptcy in 1976.

It was his divorce and the settlement that came out of it that required Gaye to pay all of the royalties from his next album to his ex-wife. The name of the record? “Here, My Dear,” which is a clever way to title the piece considering the circumstances. The royalties were meant to make up for the $600,000 of unpaid alimony to the singer’s ex-wife.

Another key factor in why Gaye was broke: his escalating and increasingly expensive cocaine habit, which saw him burn through his earnings at an alarming rate. As a result, his final years were characterized by financial struggles and addiction.

Larry King

Another popular celebrity bankruptcy example, Larry King has his own story of financial troubles. Today, King is known as a broadcasting legend, but he didn’t start out on top. His early days in the business were nothing but glamorous, with one shining example being the time in 1971 when he was charged with grand larceny after “ripping off” $5,000 from his business partner.

Even though those charges were dropped, the scandal from the story did its fair share of damage to the television journalist. The grand larceny charges made him toxic to employers, which then resulted in a four-year stretch without work. King was left with a $350,000 debt that led him to declare bankruptcy in 1978. However, later that same year he was offered a late-night radio gig in Washington, DC, which eventually morphed into his wildly successful CNN show, placing his days of financial difficulties behind him.

Tom Petty

The singer who just wouldn’t back down, Tom Petty is another celebrity who got hit by serious money woes. Petty famously declared bankruptcy in 1979, not because of any financial duress, but as a legal strategy meant to free himself from a restrictive contract with his record label. Petty discovered that he was deep in debt as a result of the common music industry practice of paying artists advances against future earnings.

His bankruptcy strategy was as follows: Petty’s lawyers informed him that when he signed his original contract, he gave away 100 per cent of his publishing royalties in exchange for a $10,000 advance. Filing for bankruptcy, however, would force the court to re-adjust his business arrangements, ultimately voiding his contract with the label.

The label was afraid that other artists would follow suit with the same strategy, so the label’s lawyers made it their mission to convince Petty not to declare bankruptcy. Says Petty: “As soon as they thought my action might set an industry precedent, they rolled out the big guns.” Looking back, Petty said, “It may have been a sham in some ways, the bankruptcy strategy. But … [the label’s] lawyers figured we’d out-lawyered them.”

Gary Coleman

One of the most popular TV icons, Gary Coleman, was a hit as a child actor earning a pretty $64,000 a week in his role as Arnold in the show Different Strokes. When the show ended and the cute child actor became a less-cute adult, the lucrative acting roles dried up and his earning dwindled.

Assuming he had millions in the bank, Coleman was shocked when he took a straight-faced look at his financial statements and saw he was broke. Wondering where all the money went, he ultimately sued his adoptive parents, whom he accused of squandering his TV fortune.

It was an expensive legal battle that was difficult enough not to mention Coleman’s ongoing medical issues, which also contributed to the drain what was left in his bank account. He filed for bankruptcy in 1999, listing debts of more than $70,000. “I can spread that blame all the way around,” Coleman said in an interview, “from me to accountants to my adoptive parents, to agents to lawyers and back to me again.”


The beloved comedian Sinbad has had two bankruptcies under his belt. The first one, in 2009, came about from a massive tax debt of more than $2.5 million. The second time, in 2013, Sinbad filed for bankruptcy due to business expenses, and he paid out of pocket to keep his company afloat and salaries paid. Sinbad had been banking on the hopes that he’d soon land a lucrative movie role that would replenish his bank account, but that thinking didn’t pay off in the end.

According to Sinbad, he spent money all with the idea that “I’ll get one more movie and I’ll wipe these bills out,” but then that movie never came. At the time of his second bankruptcy, Sinbad was reportedly in the hole for $10 million, $8 million of which came from unpaid taxes from the years 1998-2006.

Filing for Bankruptcy

If the above stories of celebrity bankruptcy have served to tickle our taste for sensation and glamour, they should also serve as a reminder that financial struggles can happen to anyone. While the prospect of restoring your credit and financial stability can feel overwhelming after a bankruptcy, it hardly compares to the negative emotions experienced before filing for one.

It takes a lot of courage to admit it’s time to file for bankruptcy, which is why it’s important to find a bankruptcy trustee in Toronto and the surrounding area who makes you feel comfortable and secure. In fact, survivors of bankruptcy are often the first ones to express the sense of freedom that comes with achieving your long-term financial goals. Even so, there’s bound to be some uncertainty and questions around how bankruptcy can impact your future credit score or keep you from achieving your long-term goals.

Trustees Understand Your Plight

Our Licensed Insolvency Trustees understand that filing for bankruptcy in Ontario is not always easy to do. We take an empathetic approach to debt relief, however, and want to help those facing insolvency get at the root of their money issues and do more than recover. We want to help those in difficult financial positions create and achieve their financial goals, and give them the financial road map they need to get through and recover from a bankruptcy.

As a reputable and well-received financial firm, our trustees are able to help those in all walks of life overcome their debt issues. We offer debt management services as well as credit counselling, which can sometimes be enough to recover from debt without the need for government-regulated debt relief like bankruptcies or consumer proposals in Canada.

We’re here to help you dealing with bankruptcy in Brampton and other areas of the GTA, and we want to see you succeed. Are you ready to take the first step towards long-lasting debt relief? Then click here for more info and get started with our services. There’s no point putting it off any longer, you deserve to regain your financial freedom. Let us show you how.

Take Your First Step Towards A Debt Free Life

If you are overwhelmed by debt, call us at 1-844-962-9200 to book a FREE, confidential appointment. We will review your financial situation in detail and discuss all of your options with you. Alternatively, you can fill out the form below and our team will reach out to you. 

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