Bert Olmstead Murray Albert " Bert " Olmstead ( born September 4 , 1926 , died November 16 , 2015 ) is a retired Canadian professional left winger who played for the Montreal Canadiens , Chicago Black Hawks and Toronto Maple Leafs in the National Hockey League ( NHL ) . Olmstead began his career with the Black Hawks in 1949 . In December 1950 , he was traded to the Montreal Canadiens via Detroit . Olmstead had his best statistical years playing for Montreal , leading the league in assists in 1954 – 55 with 48 , and setting a league record for assists with 56 the following season . Olmstead was claimed in an Intra - League Draft by Toronto Maple Leafs in 1958 , and played there until his retirement in 1962 . In the 1967 – 68 season , Olmstead served as coach of the expansion Oakland Seals . Olmstead played in the Stanley Cup final in 11 of his 14 seasons in the NHL , winning it five times . He won it four times with Montreal , in 1953 , and from 1956 to 1958 , and once with Toronto , in 1962 , which was his last season . He was inducted into the Hockey Hall of Fame in 1985 . Early life . Olmstead was born in Sceptre , Saskatchewan , a small village with a population less than 200 , in southwestern Saskatchewan . In 1944 , at the age of 18 , he moved to Moose Jaw , Saskatchewan , to play junior hockey . In his first year , Olmstead and the Moose Jaw Canucks challenged for the Memorial Cup , after finishing the playoffs with a 15 – 1 record . They were unsuccessful in the 1944 - 45 Memorial Cup Final against the St . Michaels College Majors . Olmstead had 10 goals and eight assists in the 17 playoff games he played . He played another season in Moose Jaw , before being assigned to the Kansas City Pla - Mors of the United States Hockey League ( USHL ) by the Montreal Canadiens . Playing career . Chicago Black Hawks . Olmstead played three full seasons for Kansas City , and a part of another , later in 1950 , for the Milwaukee Sea Gulls . In the 1946 – 47 season , Olmstead joined the Pla - Mors , finishing the season with 42 points in 60 games . In 1948 – 49 , the Canadiens , who had originally sponsored him and owned his rights , traded him to the Chicago Black Hawks . The same season , Olmstead made his NHL debut , called after scoring 33 goals and 44 assists , for 77 points , in 52 games , playing nine games for the Black Hawks , and collecting two assists . Olmstead played the entire following season for the Black Hawks , appearing in 70 games , and scoring 20 goals . Olmstead split the 1950 – 51 season between four teams , playing for all but one of them . He began the season playing for the Black Hawks franchise , playing 15 games in the NHL and 12 in the USHL , for the Milwaukee Sea Gulls . On December 2 , 1950 , Olmstead , with Vic Stasiuk , was traded to the Detroit Red Wings , in exchange for Lee Fogolin and Steve Black . On December 19 , 1950 , 17 days after the trade to Detroit , he was traded again , without ever suiting up for the Red Wings , to Montreal , for Leo Gravelle . Olmstead would never leave the NHL until his retirement in 1962 , playing 39 games that season on a line with Maurice Richard and Elmer Lach , scoring 38 points . Olmstead also appeared in 11 playoff games , collecting six points , as the Canadiens lost the best - of - seven Stanley Cup finals to the Toronto Maple Leafs in five games . Montreal Canadiens . Olmstead and the Canadiens appeared in the Stanley Cup finals again in the 1951 – 52 season , losing to the Detroit Red Wings ; after recording 35 points in 69 regular season games , Olmstead was limited to an assist in 11 playoff games . In his third season with the Canadiens , Olmstead and the Canadiens won the Stanley Cup for the first time . Earning 45 points in 69 games , he was named to the Second All - Star Team . On the last game of the season , Olmstead bodychecked Gordie Howe , stopping him from tying Maurice Richard ' s record of 50 goals in a season . Olmstead played all the 70 games in the next two seasons , scoring 52 and 58 points in the 1953 – 54 and 1954 – 55 seasons , respectively . The Canadiens lost to the Red Wings in the Stanley Cup finals in both seasons . In the 1954 – 55 season , Olmstead led the league in assists , with 48 . The 1955 – 56 season saw the start of Montreal ' s five consecutive Stanley Cup championships . In that season , Olmstead played on a line with Jean Beliveau and Bernie " Boom Boom " Geoffrion . He set a record for assists , with 56 , and also scored eight points in a game , recording four goals and four assists , tying Rocket Richard ' s record . This record would be broken in 1976 by Darryl Sittler , who scored six goals and four assists , for ten points . As well as winning the Stanley Cup , Olmstead was again named to the Second All - Star Team . Olmstead won two more Stanley Cups in the 1956 – 57 and 1957 – 58 seasons . After the conclusion of the 1957 – 58 seasons , doctors informed him that he had no strength left in his knees , and that he should contemplate retirement . As a result of this prognosis , the Canadiens left Olmstead unprotected in the Intra - League Draft , and he was claimed by Billy Reay , the head coach of the Canadiens ' chief rival , the Toronto Maple Leafs . Toronto Maple Leafs . Early in the 1958 – 59 season , Punch Imlach , the assistant general manager of the Leafs , fired Reay , installed himself as head coach , and appointed Olmstead as the playing assistant coach . This meant that while Imlach coached the team during games , Olmstead was in charge of the practices ; however , Olmstead only last three months as assistant coach , resigning to devote more time to improving his play . The same season , the Leafs went on a long winning streak in order to qualify for the playoffs , but they lost to the Canadiens in the finals . After losing in the Finals the next season , and falling short of the Finals the next season , the Olmstead won his fifth and final Stanley Cup in 1962 , missing two months of the season with a broken shoulder , and being limited to only four out of the 12 playoff games . Retirement . After his fifth Stanley Cup win , with Toronto , the New York Rangers claimed Olmstead in the Intra - League Draft on June 4 , 1962 . This came as a surprise to Olmstead , who refused to report to the team . The Canadiens offered to acquire him from the Rangers , within a month ; Olmstead demanded an immediate trade . Since no deal came , he retired at the age of 35 . During his 14 - year NHL career , Olmstead scored 181 goals and 421 assists , for 602 points ; in the playoffs , he collected 59 points , in 115 games . In his 14 seasons , Olmstead appeared in the Stanley Cup final 11 times . He won five times , four of them with the Montreal Canadiens , and once with the Toronto Maple Leafs . After retiring from playing , Olmstead attempted coaching . In the 1965 – 66 season , Olmstead coached the Vancouver Canucks , of the WHL ; he finished with a 33 – 35 – 4 record , for a . 486 winning percentage . In the 1967 – 68 season , Olmstead coached the expansion Oakland Seals , in the NHL . Olmstead did not last the full season , stepping aside after 64 games , having only won 11 games , with a . 297 winning percentage . Legacy . Known as " Dirty Bertie " because of physical playing style , Olmstead was a power forward , making hard hits and winning in battles in the corners . He was not a very good skater , and thus he had to compromise with his bodychecking . Olmstead was not regularly involved in fights , but in the ones he participated , the majority were started with his hits . Olmstead was inducted into the Hockey Hall of Fame in 1985 . Olmstead , with his wife Nora , visited the town of Okotoks on August 13 , 2005 , with the Stanley Cup . He had previously declined to spend a day with it , believing that it was being given to much older winners only because of the lockout . Olmstead also noted , at the end of the day , that he was happy to have the Stanley Cup again . Upon his passing the NHL released the following statement : " The National Hockey League family mourns the passing of Bert Olmstead - - a fierce competitor and a five - time champion who played in the Stanley Cup Final 11 times in his 14 - season career with Chicago , Montreal and Toronto , " NHL Commissioner Gary Bettman said . " Bert ' s passion for the game earned unwavering respect from his teammates ; his knowledge of the game once earned him a role as a playing assistant coach ; and his skill led to what was then an NHL single - season record for assists : 56 in 1955 - 56 . We send heartfelt condolences and comfort to Bert ' s family and friends . "