324. John Henry
$2.5 billion Self-made Score: & Source: sports age: 68 residence: boca raton, fla. College dropout
The Boston Red Sox co-owner dropped out of college—he was reportedly studying philosophy— but went on to make a fortune trading commodities and started an investment fund at age 32. In 2002, he and partner Tom Werner paid $380 million for the Sox; within 2 years, they had guided the team to its first World Series win in 86 years. Henry also holds stakes in Nascar’s Roush Fenway Racing and English soccer club Liverpool FC.