Cigar
1995 and 1996 Horse of the Year
Earnings: $9,999,815 ($12.5 million in 2002 dollars)

Cigar, grandson of Seattle Slew, holds the current North American money record. His career didn't take off until his fourth year, when he began an amazing 16-race winning streak, including an undefeated 1995 season. In the first-ever Dubai World Cup in 1996, Cigar ignored a cracked hoof to best a challenger, Soul of the Matter.