Collingwood has been the birthplace of many colourful sports characters over the past
seventy-five years and the Sailor must rank high on the list.

We have always thought that he never received the recognition he deserved and apparently Connie Smythe thought so too.

When Jimmy died in 1968, Smythe said, “Herberts was the most underrated player in the N.H.L. because too much attention was paid to his fun loving antics. But he was one of the best of his era and a natural hockey player.”

He had a ten-year career with Boston, Toronto and Detroit and several years with International League clubs. He also took a fling at refereeing in the British Hockey League but his antics were just a little too much for the staid English hockey promoters.

He was a star right from the start in his rookie year with the Bruins as he scored
seventeen goals and picked up ten assists in a 30-game schedule. This was a
most remarkable feat when you realize that the goal production for the whole Boston team that season of  1925 was only forty-seven goals.

The  season of 1925-26 was his best. Playing between Carson Cooper and Hugo
Harrington he scored 27 goals in 36 games and finished third in the standing
behind the great Nels Stewart and Cy Denneny. In 1927 he finished fourth in the
scoring race and the Bruins made the Stanley Cup finals for the first time. The
Ottawa Senators defeated the Bruins that season two games to nothing with two
games tied. The Sailor’s contribution was three goals.

Jimmy moved on to Toronto in the middle of the 1928 season but although Smythe valued his ability, he  refused to put up with his frolicsome behaviour and his utter disregard for training rules. He finished his N.H.L. career with Detroit where he succeeded in helping Jack Adams to acquire a cluster of ulcers. He once upset the whole scoring structure of the league by claiming two points for one goal. In a game against New York Ranges he managed to recover his own  pass and score. According to Jimmy’s calculations an assist counted a point and so did a goal. Since he was the passer and the scorer it just had to be two points for Herberts. Of course, he didn’t get away with it, but he had the official scorer puzzled for awhile.

Herberts had that race gift of showmanship that kept his name in sport pages. A Detroit writer panned him once for failing to show up for a game. Jimmy was as mad as wet hen. Not for the panning. He was ruffled because the writer misspelled his name.