Herb Gray's Canadian Football League career did not exactly get off to a roaring start. After a forgettable 1956 season with the Winnipeg Blue Bombers, the All-American from the University of Texas left the team because he did not get along with the coach. But when the Blue Bombers handed the coaching reins to his teammate, the legendary Bud Grant, Gray promptly picked up the phone and asked if he could return. The Bombers are glad he did.
For the next 9 seasons, Gray dominated as no Blue Bomber defender has dominated since: a CFL All-Star 7 times, 6 appearances in the Grey Cup Game, 4 Grey Cup victories, and a Schenley Award as the CFL's outstanding lineman in 1960 - the first time a defensive end had won the coveted award. The defensive captain for 9 years, Gray also won the Dr. Bert Oja most valuable Bomber lineman award in 1965.
Gray's tenacity on the field was admired by teammates and opponents alike. Said long-time playing partner Steve Patrick, "Herb had stamina that nobody else did. He'd be going all out on the first play of the game, and still be going all out on the last play."
Veteran sportswriter Jack Matheson remembered the respect opposing teams had for Gray's ability. "In the 1960 Western Final, the Edmonton Eskimos refused to run to Herbie's side of the field." The tactic worked, as the Blue Bombers lost the game, and missed their only Grey Cup Championship in a remarkable 5-year run.
In 1980, Gray was named the Blue Bombers' Defensive Player of the Half-Century. He was inducted into the Canadian Football Hall of Fame 3 years later, and into the Winnipeg Football Hall in 1984.