He was bred by Florida veterinarian, Dr. Al Smollin, and raced by his wife, Barbara.
He was trained by Jamaica native Ralph Ziadie from a base at Calder Race Course in Miami Gardens.
Sir Bear raced in Florida and also competed at racetracks from Ohio to the East Coast of the United States.
In 2002, at age nine, he won his third Skip Away Handicap by defeating Preakness Stakes winner, Red Bullet.
Sir Bear made his last start at age ten on January 25, 2003, in the Sunshine Millions Classic at Gulfstream Park.