While still in WWE, Flair sunk a ton of money into "Ric Flair Finance," where the "Figure Four Process" would help you secure a loan better than anybank could.. This was on top of a whole lot of alimony to his ex-wives, past tax issues that Vince McMahon bailed him out of (which he may not have paid back), etc.
After Flair did his retirement match with WWE at Wrestlemania 24 in 2008, he got so many lucrative offers for appearances that WWE wouldn't let him do that he asked for and was granted a release from his contract. The original plan had been for him to stay on in a goodwill ambassador role. At the time, it seemed like the right move since WWE was willing to take him back when he was done.
In addition to a deal with Coca Cola where he would speak at corporate events, he put himself out on the open market to independent promotions, legends convention promoters, etc. His fee was $10,000 per appearance plus a airfare for him and his assistant and he got plenty of takers. A refundable $5,000 deposit was due when confirming the booking. A company willing to pay $50,000 would be able to record and release a Flair "shoot interview DVD."
It's unknown if any other bids came in, but Highspots got the interview in a deal where they paid $100,000 for the interview and discounted appearances. The shoot interview DVD set was released several weeks later after editing several hours of footage that repeated content from Flair's book. With so much money invested in the project, a Highspots representative went on a popular wrestling DVD trading forum to say that they know that copies of their interviews being ripped and traded around is inevitable, but that they really need people to avoid it this time. The administrators of the forum then officially banned (open) trading of the set.
After Ring of Honor got TV on HDNet, they decided to bring in Flair as "ROH Ambassador." The logic was that he was a big enough star that they might be able to syndicate their TV show internationally, plus they'd get discounts for using Flair's son Reid and giving him a good learning environment as a wrestler. Not long into that run, WWE came calling. They wanted Flair involved (in a non-wrestling role) in the Chris Jericho vs legends feud that led to a gauntet match at Wrestlemania 25. As a condition of this, he cancelled his ROH bookings. He never refunded the deposits for the cancelled bookings, though. Meanwhile, Reid was arrested for heroin possession.
Highspots eventually loaned Flair money for reasons known only to them. $31,000 and $35,000 in separate transactions. Flair put up his original "domed globe" NWA World Heavyweight Title belt as collateral.
As a way of paying back the loans, Flair made two appearances and did a shoot interview DVD ("Roundtable with Ric Flair and Roddy Piper"). Highspots claimed that he still needed to make one more appearance to pay back the $31,000 loan reimburse them the cost of the photos used at the appearances, and pay for the marketing materials used to promote the appearances. The $35,000 loan was considered unpaid and owed in full plus interest.
When it became clear to Highspots that they weren't getting any more of their money back, they announced that they were auctioning off the NWA belt. Flair's lawyer asked for a 48 hour extension from Highspots, which he got, but he didn't pay up. Highspots then proceeded to announce that the belt was for sale and that only offers of $75,000 or more would be considered. It's believed that they had a concrete offer for that figure before making the official announcement.
It was then learned that Highspots couldn't sell the belt because Flair had already put it up as collateral for a (properly filed) loan from Conbraco Industries Inc., a plumbing and heating valve company. Yes, really. In addition to the belt, collateral used to get the loan from Conbraco included a replica WCW belt, Flair's wrestling gear, his WWE Hall of Fame ring, the Rolex watch inscribed with "To Be The Man" that Shawn Michaels gave him, framed magazine covers featuring Flair, an autographed Michael Jordan poster, an autographed posted of Flair and Vince McMahon, "a framed, personalized Kevin Green jersey," "commercial claims arising from a previous lawsuit Flair was involved with," and other "proceeds and products."
A few weeks later, Dave Meltzer reported that Conbraco is owned by a good friend of Flair, with the loan being done "partially" because Flair wanted to get those items away from his wife, who he was separated from at the time. Apparently, Flair was approached by a fan in one of his robes at an appearance and the fan explained that he had bought it from Flair's wife.
Meanwhile, Flair came out of retirement to wrestle Hulk Hogan on the Hulkamania Tour in Australia.
Flair signed with TNA and appeared on their infamous live January 4th, 2010 show that aired opposite Bret Hart's return to WWE on Raw.
ROH sued Flair a month after that since he never refunded their deposits and they felt the TNA deal meant he never would. The case is still pending.
When asked if Flair would be at his next convention, Legends' Fanfest promoter Greg Price told a story about how Flair held him up for more money in 2009.
Highspots (finally!) sued Flair three months after that.
A few months ago, Flair threw a tantrum and wouldn't get on the TNA tour bus when he was refused an advance during a European tour. He ended up sleeping in some guy's house in Dublin, Ireland for a few days before being brought back on the tour since he had been advertised prominently, upsetting the many wrestlers who were glad that someone put him in his place.
