Jeff Bezos & MacKenzie Scott — $38 Billion

The most expensive divorce in human history, with MacKenzie Scott receiving 4% of Amazon — worth $38 billion at the time of the 2019 settlement. This sum is 50% larger than the net worth of the #2 item's combined estate split. MacKenzie has since given away over $17 billion to charities, making her the most generous philanthropist of the 2020s, while Bezos retained 75% of their shared Amazon stock plus The Washington Post and Blue Origin. The divorce was triggered when the National Enquirer leaked his affair with Lauren Sanchez, leading to a blackmail scandal involving intimate photos. One text message started it all, costing nearly forty billion dollars.