5 Stephen and Elaine Wynn – $741 Million
When you see the name Wynn, you probably think of the decadent Las Vegas hotel and casino. Back in 2010, Steve Wynn, chairman and CEO of Wynn Resorts, finalized his divorce from Elaine, giving her more than 11 million shares of stock worth a total of $741 million. At first blush, this looks like a great payday for more than 25 years of marriage; however, it came with a catch. Elaine could only sell her shares as directed by her former husband. By maintaining control of Elaine’s shares, Wynn’s leadership position within the company remained secure. However, this may not be the case for much longer. In 2013, Elaine filed suit in federal court, requesting permission to sell the shares she was awarded in the divorce.
4 Adnan and Soraya Khashoggi – $874 Million
The fourth couple on our list married in 1961, when the bride was only 15 years old. Saudi entrepreneur and arms dealer Adnan Khashoggi divorced Soraya, his wife of 13 years and mother of his five children, in 1974. At $874 million, the Khashoggis’ divorce settlement was the most expensive in history for two decades. According to the Guardian, some time after the divorce, the couple’s daughter Petrina took a DNA test, which revealed that Adnan was not her biological father. I only have one question. What prompted Petrina to take the test in the first place? Something tells me the back story would be a great soap opera or telenovela episode. However, Adnan’s family drama is tame in comparison to his well-established bigger-than-life persona, which includes extravagant parties, high society relationships and uncanny connections to several major scandals of the late 20th century, with the Iran-Contra scandal being the most notable.
3 Bernie and Slavica Ecclestone – $1.2 Billion
When Formula One President and CEO Bernie Ecclestone divorced his wife, Slavica, of 24 years back in 2008, he made the former model Britain’s richest millionaire as a result of the divorce. Although the divorce settlement was not made public, experts estimate it to have been approximately $1.2 billion. Although there are no salacious details to report about this divorce, here is a fun fact about the former couple: Standing at a tall 6 foot 2 inches, Slavica was nearly a foot taller than her former husband. Clearly, Bernie had a healthy ego. Not every guy has the confidence to date a significantly taller woman let alone marry her. Although Bernie’s divorce didn’t result in ugly headlines, he has not been so lucky when it comes to business. In 2013, German authorities brought bribery charges against Bernie, alleging he bribed former banker Gerhard Gribkowsky, who has since been jailed, in exchange for favorable treatment in a financial transaction he managed back in 2006.
2 Rupert and Anna Murdoch – $1.7 Billion
This one is a bit scandalous. After divorcing his wife Anna of 32 years back in June of 1999, Australian media tycoon Rupert Murdock married Wendi Deng, several decades his junior, 17 days later. According to Anna, Rupert caused the marriage’s demise when he had an affair with his then-translator Wendi. What makes the divorce settlement in this case even more interesting—besides the $1.7 billion Anna received—is that $110 million of it was in cash. I wonder how he delivered it. In an armored car maybe? But, wait. Scandal followed Rupert into the business world, too. Britain tabloid News of the World, owned by Rupert, is at the center of a phone-hacking scandal that made international headlines in 2011. It is alleged that hundreds of well-known figures, ranging from actors and musicians to politicians and murder victims, had their voicemails hacked by News staffers. Rupert has since shut down the tabloid and settled several lawsuits.
1 Harold and Sue Ann Hamm – Potentially Up to $5 Billion
As of this writing, the divorce between self-made oil billionaire Harold Hamm and his second wife of almost 25 years, Sue Ann Hamm, is poised to be the most expensive divorce in history. Filing for divorce on May 12, 2012, Sue Ann alleges Harold “was having an affair.” According to Forbes’ 2013 World’s Billionaires list, Harold is worth $11.3 billion, with the majority of his wealth held in Continental Resources stock, a leading oil development company he founded and where he currently serves as chairman and CEO. If the couple didn’t sign a prenuptial agreement, Sue Ann could possibly receive up to half of Harold’s 68 percent ownership interest. If it’s true that Harold got nookie on the side, you have to wonder if it was worth it: it may cost him billions.