William Gross

World's biggest bond trader got start gambling. Arranged gambling pools while studying at Duke; spent a summer working the slots at Harrah's in Lake Tahoe. Vegas stint playing blackjack turned $200 into $10,000 in just 4 months. Vietnam vet; earned M.B.A. from UCLA. Took job as a securities analyst at Pacific Life. Discovered key to making money with bonds: trade, don't buy and hold. Given $10 million portfolio to manage in 1973; already earning $20 million bonuses by the 1980s. Bond division spun off to create Pimco; public offering in 1994. Netted personal $400 million in 2000 sale to German insurance goliath Allianz AG for $4.7 billion. Stamp collector sold British stamp hoard for $9.1 million last June to benefit Doctors Without Borders. Bill and Sue Gross’ messy split minted a new billionaire and dragged down another. Sue filed for divorce in 2016 from her husband, the founder of asset-manager Pimco, and she walked away a year later with a $1.3 billion fortune. That haul included a $36 million Laguna Beach house and “Le Repos,” a contested 1932 Picasso painting that she later sold for $35 million. While Bill originally tried to hang on to one of their three pet cats, Sue eventually got custody of all of them. Bill lost his spot on The Forbes 400 in 2018 following 14 consecutive years on the list. Both now run their own charitable vehicles.