Herbert played the centre forward position for six seasons in the National Hockey League (NHL) for the Boston Bruins, Toronto Maple Leafs and Detroit Cougars.
[7] Herbert's nickname of "Sailor" arose for his work as a deckhand on Great Lakes sailing ships during the off-seasons.
Herbert played three and a portion of a fourth season with the Bruins before being traded to the Maple Leafs in December 1927.
[9] The trade of Herbert to Toronto was attributed by Conn Smythe as the start of his feud with Art Ross, the Bruins general manager.
According to Smythe, "My directors were sitting beside me the first time Herberts was sent out in a Toronto uniform and I almost fainted when he caught one of his big skates on the ice and fell flat on his face.