10 of the most expensive celebrity divorces, as Sylvester Stallone’s wife Jennifer Flavin files for divorce

Sylvester Stallone’s wife Jennifer Flavin has filed for divorce after 25-years of marriage and three children.

The reason for the divorce has not yet been announced - however, many Hollywood marriages don’t last as long as the couple did.

The actor, best known for his role in boxing film series Rocky, met Jennifer in 1998 - when she was just 19 and he was 41.

They got married in London in 1996 but had a break during their relationship, after Sylvester admitted to cheating with model Janice Dickinson.

They went on to have three daughters; Sophie, Sistine and Scarlett - and Sylvester has two sons from his previous marriage.

The settlement Sylvester and Jennifer will come too is unknown.

However, BPP University Law School has rounded up a list of the most expensive celebrity divorces of all time.

Jeff Bezos and MacKenzie Bezos

Settlement: $38 billion

Amazon’s Jeff Bezos and his wife MacKenzie announced their divorce in January this year, after 25 years of marriage and four children.

The couple’s divorce settlement totalled up to $38 billion - based on Jeff’s reported net worth of $137 billion.

Subsequently, he transferred a quarter of his then 16% Amazon stake to MacKenzie.

Alec Wildenstein and Jocelyn Wildenstein

Settlement: $3.8 billion

Jocelyn won a reported $3.8 billion divorce settlement in 1999, when the pair split after 21 years of marriage.

The high-profile divorce proceedings resulted in Jocelyn being awarded $2.5 billion and $100 million per year for the following 13 years.

The divorce came after Jocelyn walked in on her husband, while he was with a Russian model at their family home in New York - and Alec reportedly threatened her with a gun, which resulted in him spending a night in jail.

Alec later married Liouba Stoupakova in 2000, and he passed away in 2008.

Kim Kardashian and Kanye West

Settlement: $2.1 billion

Kim Kardashian and Kayne West’s divorce has been named the biggest ever separation in Hollywood, thanks to their combined net worth of $2.1 billion dollars.

The pair were together for nearly seven years, and had four children.

However, they signed a prenuptial agreement before they got married, so both Kim and Kanye independently own their biggest sources of income.

Singer Kayne walked away with $1.26 billion, while Kim occupied $750 million.

They were then left to divide just 5% of their total net worth at $70 million dollars.

This was Kim’s third marriage - after Kris Humphries and Damon Thomas.

Rupert Murdoch and Anna Mann

Settlement: $1.7 billion

Businessman Rupert Murdoch and his wife Anna Mann separated in 1999, after 32 years of marriage and three children together.

Murdoch controls a media empire that includes channel Fox News, The Times of London and The Wall Street Journal.

Under the divorce settlement, $1.7 billion of Rupert’s huge fortune went to Anna, of which included $110 million in cash.

The same year that Rupert and Anna got divorced, he married Wendi - which lasted for 13 years.

He has since been married to Jerry Hall from 2016.

Bernie Ecclestone and Slavica Radic

Settlement: $1.2 billion

Formula One Executive Bernie Ecclestone famously divorced his wife Slavica Radic back in 2009, after 25 years of marriage and two daughters.

A staggering $1.2 billion dollars of Bernie’s forture went to Slavic after they settled their divorce amicably.

Bernie then married Fabiana Flosi in 2012.

Mel Gibson and Robyn Moore

Settlement: $425 million

Actor Mel Gibson and his wife Robyn Moore separated in 2011, after over 30 years together and seven children.

Robyn received a whopping $425 million - the largest divorce payout in history.

When the divorce was announced, it was revealed that Gibson and Moore did not have a prenup agreement, which meant that she was able to walk away with half of what he had earnt across his career during their 30 year marriage.

Mel has been dating actress Rosalind Ross since 2014.

Michael Jordan and Juanita Vanoy

Settlement: $168 million

Michael Jordan’s divorce from his wife Juanita Vanoy in 2006 is also among some of the most expensive in history.

Juanita initially filed for divorce from the star in 2002, after he was caught with other women - however, she withdrew her petition a month later.

Four years down the line, the pair released a statement that they had split after 17 years of marriage, due to irreconcilable differences.

As a result, Vanoy received $168 million in the divorce settlement and Jordan was also forced to pay $2.1 million in legal fees.

Michael has since been married to model Yvette Prieto since 2013.

Tiger Woods and Elin Nordengren

Settlement: $110 million

Professional golfer Tiger Woods and his wife Elin Nordengren split in 2010, after his name hit headlines for having affairs with multiple women.

The sports star is estimated to be worth a huge $1.7 billion dollars according to Forbes, and had to hand over $110 million to his wife of six-years when the divorce was settled.

Elin also received child support of $20,000 a month and acquired the family home in Windermere.

The Swedish model is currently dating American footballer Jordan Cameron, after meeting in 2019.

Madonna and Guy Ritchie

Settlement: $75 million

Singer Madonna split from her husband Guy Ritchie in 2008, after an eight year marriage and two children (one adopted).

She was ordered to pay her director ex $75 million of her $490 million dollar net worth at the time.

Guy also received their family home and the pub that the couple co-owned.

The divorce remains one of the most expensive in UK history.

Guy has since married Jacqui Ainsley in 2015, who he had had three further children with.

While Madonna has not remarried, she was previously married to Sean Penn, and had a child with actor Carlos Leon, as well as two further adopted children.

Paul McCartney and Heather Mills

Settlement: $48.6 million

Model Heather Mills and Beatles singer Paul McCartney called it quits in 2006, however the divorce took two years to settle.

Heather was awarded $48.6 million from Paul, after originally aiming to get $250 million.

Prior to his marriage with Heather, the singer was married to Linda for nearly 30-years.

He has now been married to Nancy Shevell since 2011.