Jimmy Herberts was born in Cayuga, Ontario back in 1897. He earned the nickname Sailor because he worked as a deckhand on tanker ships on the Great Lakes. He always answered "Ahoy" when directly addressed as Sailor.
He was not a noted amateur star, but became in Boston in 1924-25, he became a star, especially when teamed with Carson "Shovel Shot" Cooper. The duo were dynamic thanks to their quick, short passing game that confused defenses.
The balding Herberts was an early fan favorite in Boston. He was Boston's key man, getting Hart Trophy votes in both of his first two seasons. He scored 17 goals in 30 games in 1924-25, then 26 tallies in 36 games in 1925-26. Furthermore, his brilliant playmaking was credited as the main reason for Cooper's 28 goal outburst in 1926.
Some things never change in Boston, and one of those is Bruins' fans' love of hard nosed hockey. The short tempered Herberts certainly met that standard, using either fist or stick.
Unfortunately his tempered cost him dearly from time to time. He led the Bruins in penalty minutes in his rookie season. In the 1927 Stanley Cup finals he was disgraceful in his attempts to intimidate the referee, resulting in a $50 fine. History has tended to forget his misgivings thanks to his more notorious teammates like Eddie Shore, Sprague Cleghorn and Lionel Hitchman.
With 8 goals (and 22 PIMS) in the opening 12 games of the 1927-28 season, Herberts was off to another strong start. But his heavy drinking and abrasive personality was wearing on the Bruins, so they traded him to Toronto in exchange for Eric Pettinger and cash.
Herberts never got untracked in Toronto, scoring just 7 goals in 31 games to finish the season. He was moved to Detroit before the next season, but in 2 seasons in the Motor City he continued to struggle.
Later in life he was part of a disturbing scandal where he was charged with drunken driving and badly assaulting his estranged wife. She survived, though barely as she was left lying battered and beat on a highway and was almost run over by a passing motorist. Police found Herberts passed out in his car further down the road. When he came to, he could not remember anything.
Herberts settled in Collingwood, Ontario, operating a tourist retreat with cabins on Wasaga Beach. He also coached and refereed for years.
Sailor Herberts died of cancer in 1969.