Born in Cayuga, Ontario, Herbert was one of five children of John and Annie Herbert (daughter Maria, sons John, Norman, Charlie and Jimmy). Between the 1901 Census and the 1911 Census, the family moved to Collingwood, Ontario. It was in Collingwood where Jimmy played youth hockey. During his professional career, his name was consistently misspelled from his birth name of Herbert to Herberts. After he retired from active play, Herbert became a referee in the Maritime League. He also opened a tourist camp near Collingwood, Ontario. Later in the 1930s, Herbert refereed in the British Ice Hockey Association. In 1945, Herbert was reported as working in the shipyards of Halifax, Nova Scotia. Herbert died in Buffalo, New York after a long battle with cancer in 1968. Herbert\'s nickname of "Sailor" arose for his work as a deckhand on Great Lakes sailing ships during the off-seasons.\n', '

Herbert played senior amateur hockey from 1922 with the Hamilton Tigers of the Ontario Hockey Association (OHA), followed by a season with the Eveleth Rangers of the United States Amateur Hockey Association (USAHA). He made his professional debut with the Boston Bruins in 1924–25, scoring 17 goals in 30 games. Herbert played three and a portion of a fourth season with the Bruins before being traded to the Maple Leafs in December 1927. At the end of the 1927–28, he was traded again, to the Cougars where he played a full season and part of the 1929–30 season before being demoted to the minor pro London Panthers of the International Hockey League (IHL). He played two more full seasons in the IHL, before ending his career after nine games in the 1932–33 season.\n', '

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. The crowd roared with laughter, the directors moaned and I nearly fainted. When I was able to take another look at Herberts, there was our $17,000 prize beauty lining up with the visiting Chicago Black Hawks." Herbert was traded to Detroit at the end of that season.\n', '

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