Reg Fleming Reginald Stephen " The Ruffian " Fleming , ( born April 21 , 1936 in Montreal , Quebec ) was a professional player in the National Hockey League with the Montreal Canadiens , Chicago Black Hawks , Boston Bruins , New York Rangers , Philadelphia Flyers and Buffalo Sabres . He also played for the Chicago Cougars of the World Hockey Association , as well as a number of minor league teams in other professional leagues . His professional career spanned over 20 years . He was known as an aggressive and combative player who could play both forward and defence , as well as kill penalties . After a junior career for two seasons with the Montreal Junior Canadiens of the Quebec Junior Hockey League ( QJHL ) and one year with St . Michaels College Majors of the Ontario Hockey Association ( OHA ) , Fleming began his minor - pro career in the Hab ' s farm system with the Shawinigan Falls Cataractes of the Quebec Hockey League ( QHL ) , followed by stops with the Rochester Americans ( AHL ) and Kingston Frontenacs ( EPHL ) . His rugged style of play earned him a three game tryout with the Canadiens late in the 1959 - 60 season . That summer Montreal and the Chicago made a large nine player trade and Fleming became a member of the Black Hawks . Fleming played four full seasons on a talented Chicago club with stars like Bobby Hull , Stan Mikita , Glenn Hall and Pierre Pilote . Fleming ' s aggressive style of play added an important physical presence to the Black Hawks and helped the team win the Stanley Cup in 1960 - 61 , Fleming ' s first in Chicago . Fleming scored an important goal in the final game of the NHL semi - finals against Detroit that year . He assisted on Bobby Hull ' s 50th goal the following season , helping Hull match the NHL record . A popular player with Chicago , he was known for his grit and team spirit . His involvement in a number of notorious incidents gave him a reputation around the league as a tough customer and an intense competitor . Prior to the 1964 - 65 season , Chicago dealt Fleming to the Boston Bruins . Used primarily as a forward , he recorded personal highs of 18 goals and 23 assists in 1964 - 65 . Midway through the next season , he was traded to the New York Rangers . He would spend the remainder of that year and the following three with a rapidly improving Ranger club . Although a popular and consistent performer with the Rangers , he was sent to the Philadelphia Flyers for the 1969 - 70 season . His experience and combativeness helped the small and unaggressive Flyer team . Left unprotected in the 1970 Expansion Draft , Fleming joined the Buffalo Sabres , where he recorded his career high in penalty minutes in 1970 - 71 , his last NHL season . After minor league stints with Cincinnati Swords ( AHL ) and Salt Lake ( WHL ) in 1971 - 72 , Fleming returned to Chicago , joining the Cougars of the newly - formed WHA . After scoring 23 goals and playing his usual rugged style in 1972 - 73 , injuries began to reduce his effectiveness the following season , his final season in the WHA . After playing for a few more seasons in the minors in the mid - western United States , Fleming retired in 1978 . In the NHL Fleming scored 108 goals and 132 assists in 749 regular season games and 3 goals and 6 assists in 50 playoff games . In the WHA he scored 25 goals and 57 assists in 120 regular season games and 4 assists in 12 playoff games .