His first client was James Norris, owner of the Detroit Red Wings of the National Hockey League, for whom he would win the 1938 Metropolitan Handicap with Danger Point.
[6] Hayward moved to the East Coast of the United States in late 1952 to take over as head trainer for Harry Gugenheim's Cain Hoy Stable.
[7] As at 2011, Hayward's win with Dark Star in the Kentucky Derby remains one of the biggest upsets in the history of the race.
[8] Hayward resigned from Cain Hoy Stable in December 1954 and took over as trainer for a racing partnership headed by Dallas Cowboys owner Clint Murchison.
He added to his clientele with the Circle M Farm of Edward S. Moore and in the 1970s took over training of future Hall of Fame inductee Forego for the Lazy F Ranch stable when Sherrill Ward fell seriously ill in 1975.