Divorce can mean heartbreak or it can mean relief. For the fabulously wealthy, divorce can also mean the loss of up to half of the richer spouse’s net worth.

Some couples sign prenuptial agreements to protect their fortunes, while others enter postnuptial agreements. For many, though, the only agreement was saying "I do." When the legal fees of high-profile lawyers are no object to either party, all agreements are there to be challenged in the courts. The arguments usually end with the divorce judge having the final say.

1. Alec Wildenstein and Jocelyn Wildenstein (M. 1978–1999)

When their marriage fell apart, the Wildensteins had an estimated $5 billion fortune to divide, including million-dollar artwork, a Gulfstream jet, a horse racing stable, multiple homes around the world (such as a five-story Manhattan townhouse), a Virgin Island compound, a chateau in Paris, and a 66,000-acre Kenyan ranch. They wed in Las Vegas and the marriage lasted 19 years, producing one son and one daughter. Alec’s lawyers claimed that their client earned only $175,000 a year, as the purse strings were held by the dynasty patriarch, Daniel Wildenstein. For two years, the parties argued and the prolonged divorce proceedings eventually exposed the couple’s lavish spending habits. A Manhattan court dismissed Alec’s claims of penury and awarded Jocelyn around $2.5 billion.

2. Harold Glenn Hamm and Sue Ann Arnall (M. 1998–2014)

During the contentious divorce proceedings, Oklahoma oil tycoon Harold Hamm was estimated to be worth anywhere between $9 billion and $18 billion, depending on whose lawyer was doing the talking. There was no prenuptial agreement. The Oklahoma divorce judge determined that the value of the assets during the marriage was something out of the control of both parties (rising oil prices), and was not a result of the efforts or skills of either spouse. After 26 years and two children, Sue Ann was awarded alimony of just under $1 billion. Harold lauded the judgment as "fair and equitable." Sue Ann, who had expected a few billions, called it "unfair" and vowed to appeal.

3. Stephen Wynn and Elaine Pascal (M. 1963–1986) and (M. 1991–2010)

Billionaire CEO Wynn was the operator of high-end hotels and casinos. In 2002, Wynn founded Wynn Resorts Ltd, a Paradise, Nevada-based company. The couple married each other twice over a 46-year period and has two daughters. The dissolution of the marriage was amicable and Wynn described his wife as critical to the company’s success. In addition to valuable artwork and real estate holdings, Elaine received 11 million shares worth $741 million in Wynn Resorts. The transferred shares were considered community property under Nevada State law. Today, their value is estimated to be over $1 billion.

4. Craig McCaw and Wendy Petrak (M. 1974–1997)

The Seattle telecommunications billionaire was said to be worth $1.5 billion when his marriage to Wendy crumbled. Most of this wealth was attributed to the sale of the McCaw Cellular Company to AT&T in 1994 for $11.5 billion. The couple split up one year after the sale. There were no children. Wendy sought half the value of the assets acquired during the marriage, as is permitted under the laws of Washington State. Each spouse hired over 30 forensic financial experts, and thousands of documents were scrutinized by the parties. After court proceedings lasting almost three years, Wendy was awarded $460 million.

5. Mel Gibson and Robyn Moore (M. 1980–2009)

The star of Mad Max and director of The Passion of the Christ was hit hard financially when his marriage to Robyn ended. Together, the couple had seven children and owned properties in the U.S., Australia and Costa Rica, as well as a $15 million Fijian island. They separated in July 2006, the day after Gibson was arrested for DUI and accused of using anti-Semitic slurs. There was no prenuptial agreement and a Los Angeles court signed off on a $400 million settlement to Robyn, which represented half of Gibson’s fortune. She was also granted half of his film rights, as well as half of his Screen Actors Guild pension and Directors Guild of America pension.

6. Robert Johnson and Sheila Crump (M. 1969–2002)

Robert and Sheila co-founded Black Entertainment Television (BET) in 1979, aimed at African-American audiences. Over the years, Sheila grew increasingly concerned about the sexually explicit broadcast material, finding it increasingly demeaning to women and young girls. Robert viewed the output as purely for entertainment and not education. The couple grew apart and the company was sold to Viacom in 2000 for $3 billion. Sheila’s divorce settlement was an estimated $400 million, ranking her second to Oprah Winfrey on the list of wealthiest African-American females in the USA.

7. Michael Polsky and Maya Polsky (M. 1975–2006)

The couple married in the Soviet Union and moved to the USA in 1976 with $500. In 1980, they moved to Chicago and Michael, an engineer, became successful in the energy business, eventually becoming the CEO of Invenergy LLC. Michael’s lawyers argued that Maya was a homemaker and art gallery owner who did not contribute significantly to the business; however, a Chicago court awarded Maya $183 million out of a $367 million estate. The $183 million award was considered a just division of the marital property, reflecting the contributions of each party to the acquisition and increase in the value of the said property, as well as the length of the marriage.

8. Michael Jordan and Juanita Vanoy (M. 1989–2006)

NBA star Michael Jordan’s marriage ended after 17 years and three children. The former Chicago Bulls and Washington Wizards player wed in Las Vegas in 1989, five years after he joined the NBA. Jordan was well known for his many professional talents as well as for his multiple product endorsements, with Nike’s Air Jordan sneakers reported to be particularly lucrative. The pair had first filed for divorce in 2002 before reconciling for a few years. Juanita’s settlement was estimated at $168 million plus a lavish Chicago mansion and custody of the children.

9. Neil Diamond and Marcia Murphey (M. 1969–1995)

Diamond—the popular crooner of "Sweet Caroline," "Beautiful Noise" and "Love on the Rocks"—has sold over 100 million albums worldwide in a career spanning over 50 years. His 26-year marriage to Marcia produced two children. The $150 million settlement represented half of the singer-songwriter’s fortune, but theirs was an amicable split and Diamond reportedly described Marcia as "worth every penny."

10. Frank McCourt and Jamie Luskin (M. 1979–2011)

The owners of the Los Angeles Dodgers filed for divorce in 2009 after 30 years of marriage. Their lawyers argued over whether the Dodgers' assets were community property owned 50-50 by the couple, or separate property owned solely by Frank. At stake was a $722 million asset. The proceedings dragged on for years and Jamie eventually settled for $150 million, having given up co-ownership of the Dodgers.