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10 Ridiculous Ways Ric Flair Wasted Money

Before Charlotte Flair graced the stage in WWE, her father was setting the image for what it would mean to embrace the Flair name. The “stylin', profilin', limousine riding, jet flying, kiss-stealing, wheelin' and dealin' son of a gun” is known for the lavish way that he carried himself, wearing Rolex watches and portraying an image of wealth outside the ring.

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Despite this image being attributed to his character, the real-life Ric Flair was a bit of a wasteful spender. Making well over $700,000 per year for a good stretch of his career, one would assume that Flair ranked relatively highly in net worth with his counterparts, however many claim that his net worth is nowhere near the assumed level it should be. While many factors can influence this, here are 10 ridiculous ways that Ric Flair has spent his money over the years.

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10 Ric Flair Finance

In September of 2007, Flair started an online company called Ric Flair Finance, with the purpose of acting as the middleman between lenders and borrowers seeking information for loans. Flair would spend significant time and money advertising the service before its inevitable bankruptcy in July 2008.

But why was this bankruptcy inevitable? Well, besides having virtually no basis of expertise on any financial matter, Flair neglected to obtain a broker’s license prior to engaging in any activity with this business. Unsurprisingly, the state of North Carolina frowned upon this action and fined the company before shutting it down. This illegal business cost Flair a significant sum of money and garnered absolutely nothing for the cost.

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9 Alimony

Love doesn’t always last forever. Being completely fair, this isn’t necessarily a reckless spending pattern of Flair’s; however, the court-ordered expenditure can’t really be ignored in a discussion of why he doesn’t have more money. Unfortunate for him to be sure, imagine what Flair’s net worth might look like if he wasn’t sending so much money to failed marriages.

While Flair is hardly the first to have experienced a failed marriage, he has one-upped most of us on the ramifications of his failures. All four of Flair’s ex-wives are receiving alimony from the two-time Hall of Famer.

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8 Legal Trouble

Flair has seen his fair share of skirmishes with the law. Everything from incidents of road rage to sexual harassment stained the legacy of the former champ. Legal woes are never a solid investment. At their best, these misfortunes are life lessons learned. Even with the best lesson, the cost of a misdemeanor offense is more than one typically has laying around. Even if Flair had the extra funds to cover his offenses, there would have been much better allocations of this money.

The most nonsensical of these events are tied to the infamous “Plane Ride From Hell.” In short, Flair was a bit too comfortable on this trip and assaulted two flight attendants. While he denied the accusations, Flair agreed to settle the case outside of court, raising suspicion of whether the allegations were true. This was an expensive ordeal regardless.

7 Back Taxes

Every year at tax time, we all add up the final tally, squeezing every deductible we can find into any nook that we can to increase our odds of receiving money back from the IRS. It’s a routine which American’s know by heart and one which is mandated by the federal government.

But Ric Flair seems to have missed the memo a few times on this. In the 1980s and 1990s, Flair apparently missed paying his taxes a fair few times. Given that this is a requirement of all American citizens, and one which is monitored, Flair could have saved himself additional fines and fees had he simply paid the taxes owed at the time they were due.

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6 Alcohol Abuse

While there isn’t an exact figure to reference here, it is common knowledge that Flair suffers from alcoholic cardiomyopathy. This condition is the result of long-term alcohol abuse and ultimately can lead to heart failure.

Besides this condition and the numerous backstage stories of Flair engaging in alcohol abuse, most fans were aware of his condition at the press conference for WWE 2k14. If you aren’t, the videos are widely available. To summarize the situation, Flair made multiple references to alcohol throughout the conference and was clearly inebriated throughout. While most of the focus for this event would fall on JR’s release following the event, Flair’s demeanor was a perfect representation of this facet of his life.

5 Wardrobes

Take a moment to look up a video where Flair was still in the ring. Look at the attire he wore. Lavishly decorated coats which make one wonder what practical purpose it could ever have been decorated for. When he isn’t sporting one of these coats, Flair is typically seen in a nice suit with a Rolex on and any number of other expensive accessories. To give an example, Flair once recounted spending $40,000 on a fur coat.

Flair definitely looked at the image of success, and in an industry such as professional wrestling, appearances are key. But the practicality of such expenditures in the face of mountains of debt make one question the wisdom behind the transactions.

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4 Limousines

In the same vein as his wardrobes, Flair was known to allow a very generous travel budget for himself. Known to travel by limo in order to maintain his appearances, Flair likely spent well in excess of what the typical performer would in travel.

All told, this also likely enabled Flair to further spend on his alcohol abuse. Given his partying nature, it seems unlikely that The Nature Boy would pass on fully stocking a limo with the appropriate amount of alcohol to last any distance he might be traveling.

3 Loans

The details of why they were taken are unclear, but the fact that Flair took many loans over the years to pay for business and personal expenses is well documented. The most well known of these loans were the two Flair borrowed from Highspots Inc. which led to significant legal drama between the two parties.

Discussing Flair’s dishonest tactics in acquiring these loans by using collateral already on the line for other expenses would lead to a separate topic altogether. The fact that Flair has taken so many loans over the years and opted to pay such enormous amounts of interest which much accompany them, not to mention legal fees for defaulting on them, is insane.

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2 Engagement Ring

Flair’s fifth marriage to Wendy Barlow became official in September 2018. Shortly after their engagement, images of the engagement ring he had bought her began surfacing in news and online. While it isn’t officially known, rumor has it that the engagement ring cost upward of $100,000.

Looking at images of the ring, one can tell that it took a substantial amount of money. Given that every item on this list has led to an accumulation of debt for Flair, it has to be questioned whether or not this amount of money was appropriate given his track record.

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1 The Man

This one might not be fair given its speculative nature, but it is ridiculous nonetheless. At present, in September of 2019, Flair is seemingly preparing to sue WWE for trademark rights to “The Man.” Let that sink in for a moment.

WWE, where Flair has been inducted into the Hall of Fame multiple times. The same WWE which is ran by Vince McMahon, who has personally lent money to Flair to alleviate debts and back taxes. WWE where Flair continued to wrestle well past his prime and is still paid to make appearances periodically. If the indications are true, Flair will soon bite the hand which has fed him the most, and the hand which owns the foundation to his legacy.

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