Jeff Bezos & MacKenzie Scott — $38 Billion

The most expensive divorce in human history. MacKenzie received 4% of Amazon — worth $38 billion at the time of the 2019 settlement. She's since given away over $17 billion to charities, making her the most generous philanthropist of the 2020s. Bezos kept 75% of their shared Amazon stock plus control of The Washington Post and Blue Origin. He started dating Lauren Sanchez before the divorce was finalized. The tabloid leak (via the National Enquirer) that exposed the affair led to a blackmail scandal involving intimate photos. $38 billion. One text message started it all.