He was bred by Canadian mining magnate Arthur W. Stollery at his Angus Glen Farm in Markham, Ontario, and raced under his wife Helen's name.
After his two-year-old racing season in which he was voted the Canadian 2-Year-old Champion, Kennedy Road underwent an operation to remove a bone fragment from a hind ankle.
At age five, Kennedy Road's owners sent him to California under the care of future U.S. Hall of Fame trainer Charlie Whittingham.
In what appeared to be a dead heat, Kennedy Road finished second in the Santa Anita Handicap by a fraction of a nose to stablemate Cougar II.
Brought back to Canada under junior trainer Clarke D. Whitaker, Kennedy Road set a track record in a six-furlong race at Woodbine Racetrack (1:08 3/5) that stood for more than two and a half decades.