John Henry
1981 and 1984 Horse of the Year
Earnings: $6,591,860 ($13 million in 2002 dollars)

Sold for only $1,100 as a yearling, John Henry earned more than $6.5 million in his career, setting a world record at the time. Adjusted for inflation, his winnings make him the richest horse in this gallery. His second owner gelded the aggressive, poorly-formed colt in hopes of taming his temper. John Henry improved with age; in eight seasons of racing, the improbable champion racked up 39 firsts, 15 seconds, and 9 third-place finishes in 83 starts.