Jim was tabbed as a "can't miss" big leaguer after his two junior seasons with the Toronto Marlboros (1958-60). It would, however, take him seven seasons before he made it big in the NHL, scoring 21 goals with Toronto Maple Leafs in 1966-67. He also topped all playoff scorers with 7 goals and 15 points that season. Before that he had played in the EPHL for the Sudbury Wolves and AHL for the Rochester Americans. He also had three stints with Toronto, always creating a puzzle to why a player of his talent - good speed, fine shot and combative attitude - could miss.
The turnaround for Jim was when Leafs coach / GM Punch Imlach put him on a line together with Pete Stemkowski and Bob Pulford. They clicked immediately and led Toronto to the Stanley Cup. Jim scored the Cup winning goal in 1967, the last time Toronto won the Stanley Cup. "You can't top anything like that," Jim said. " That is something you can only dream of."
Jim couldn't quite match his fine effort the following season and only scored 13 goals in 58 games. Unfortunately Jim's days in Toronto were numbered when he couldn't get along with Punch Imlach. Jim always said what was on his mind and that didn't sit well with his coaches. Don Cherry - who coached Jim in Rochester - recalled in his book that Jim had "the most cutting tongue of any person I have ever met, cruel and to the point."
Jim agreed that he got himself in trouble on many occasions thanks to his frankness.
"I always said what was on my mind, whether it was good or bad. That's the type of person I was then, and still am now. I figured that if I played hard, day in and day out, then everyone should as well," Jim said. "That's how I got into trouble several times over contracts. I believed in a fair day's work for a fair day's pay. I could never figure out why a guy who got paid more than me, produced less statistically than me That's why I felt I should be paid more. But guys like Punch Imlach didn't agree with me. That's why I couldn't get along with Punch at the time I played with the Leafs."
In those days players didn't hold out for money like today. If they tried a stunt like that they were black balled in the NHL. So it was 'sayonara' Toronto...Jim was shipped to Chicago on May 23 for Pierre Pilote and spent the next seven seasons in the Windy City.
Jim mostly played on a line together with Pit Martin and Dennis Hull. They were dubbed the "M.P.H. Line" Jim had a very productive career in Chicago (30, 28, 22, 27, 41, 32, 36 goals and 70, 53, 45, 48, 92, 73, 63 points), but never got the appreciation from the Chicago fans or press that he deserved. His relationship with reporters was never good due to his sharp tongue and bluntness. But the fans probably didn't appreciate his play as much as they should have. Maybe it was because he was never afraid to make an unorthodox move just to foil the opposition. When the play backfired he could look bad personally. But he was always willing to sacrifice his own glory for the team's benefit.
Jim never won the Cup in Chicago but was close on a couple of occasions.
"There is no doubt in my mind that we could have won two or three Stanley Cups in Chicago," Jim said. "I don't think we lost because of a lack of talent. We had the talent with guys like (Bobby) Hull and (Tony) Esposito. Hull could fire the puck into the net. Esposito could stop them in goal. Unfortunately we ran into a stopper from the team we would face in the playoffs. I guess the year that sticks out most for me was in 1971 when we lost to the Canadiens, or should I say their goaltender, Ken Dryden. Dryden was just unbelievable. He stopped almost everything we threw at him. He was the difference in the Canadiens winning the Stanley Cup that year."
Jim's days in Chicago were over on June 1, 1975 when he was traded to the Cleveland Barons. He never hit it off in Cleveland as he got shelved with a back injury. He only played 32 games in 1975-76, scoring 19 points. The following season he played even fewer games (24) and decided to hang em' up.
During his 14-year NHL career Jim developed into a fine two-way hockey player who was very sharp in front of the net. He was hard to move from the slot and he scored a lot of goals on rebounds and tip-ins.
After his playing career was over he moved back to Chicago and worked as Blackhawks director of U.S. scouting.