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What's at Stake in Angelina Jolie and Brad Pitt's Divorce: Combined Fortunes Estimated at $500 Million

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Angelina Jolie filed for divorce from Brad Pitt after two years of marriage citing irreconcilable differences on Monday – and as two of Hollywood’s wealthiest stars, there’s a lot at stake between the pair.

While estimates of their earnings vary, celebrity estate attorney Donald David approximates Pitt, 52, to be worth up to $350 million and Jolie, 41, up to $275 million, noting that Jolie in recent years, has had “a smaller industry footprint.”

“The reason for the disparity is Pitt has a bigger inventory,” David tells PEOPLE. “And a higher value and a higher residual interest.” The disparity could be the result of Jolie’s taking a step back from the big screen while Pitt took on roles in high-grossing films.

Pitt is a co-owner of production company Plan B, which produced lucrative hits like World War Z as well as Oscar contenders 12 Years a Slave and The Big Short. He’s also starred in big-budget movies over three decades, including Fight Club, Ocean’s Eleven and The Curious Case of Benjamin Button.

Meanwhile in recent years, Jolie took on a few high-salaried blockbusters like Salt and Maleficent, and directed Unbroken, but mostly focused on her own, less commercial directorial projects like In the Land of Blood and Honey, By the Sea, and her upcoming Netflix movie about the Cambodian genocide, First They Killed My Father.

Family law and divorce attorney Marilyn Chinitz estimates that the actors have a combined worth of up to $500 million and, according to Forbes, the bulk of that sum is thanks to Pitt.

Forbes estimates that Pitt and Jolie have earned a combined $117.5 million since tying the knot in 2014 (and $555 million combined since 2004). Forbes reports Pitt brought in the sum of the cash, making $76.5 million during that time period – nearly double what Jolie brought in.

David notes that films Jolie has acted in, over the span of her career, have grossed a total of $2.1 billion and films she has produced and written total to about $359 million. But, he adds, “Pitt’s films have grossed approximately more … but he has also been in more films and his films stretch back much further, meaning that their likelihood of generating [more] income is likely to be less.”

David says that between high-powered lawyers, accountants and experts both stars could shell out up to $1 million each on the proceedings.

The couple also share an impressive real estate empire including their French countryside villa Chateau Miraval, a $6.5 million New Orleans mansion, a sprawling Los Feliz home and an apartment in the Waldorf Astoria Towers, adjacent to the famed hotel, in New York City.

FLASHBACK: Brad and Angelina at the 2012 Golden Globes

Legal experts say that while the public’s eyes may be on the high-paid couple’s money, and how it could affect divorce proceedings, Jolie and Pitt likely have an agreement in place, though it is unclear if they have a prenuptial agreement.

“I would be somewhat surprised if there wasn’t some kind of prenuptial agreement. I would think that the financial aspects of the divorce are probably not going to be as difficult,” Jacqueline Newman, a New-York based lawyer who deals with high-net-worth and high-profile clients, tells PEOPLE.

“They were only married in August of 2014 … it was actually a very short marriage. My guess is that they are going to take the high road and settle this case out of the courts.”