Man o' War
1920 Horse of the Year
Earnings: $249,465 ($2.2 million in 2002 dollars)

This leggy chestnut horse, known as "Big Red," was born in 1917 and raced in the 1919 and 1920 seasons. He won 20 of his 21 races, smashing American records, and came in second just once, losing the Sanford Stakes to a horse named Upset. The wildly popular Man o' War retired to a successful 27-year stud career.