Doug Gilmour Douglas Robert Gilmour ( born June 25 , 1963 ) is a Canadian retired professional player who is the current general manager of the Kingston Frontenacs ( OHL ) . During his NHL career , he played for the St . Louis Blues , Calgary Flames , Toronto Maple Leafs , New Jersey Devils , Chicago Blackhawks , Buffalo Sabres and Montreal Canadiens . Gilmour won a Stanley Cup with the Flames in 1989 and the Frank J . Selke Trophy as the NHL ' s best defensive forward while with the Maple Leafs in 1993 . Gilmour was inducted into the Hockey Hall of Fame in 2011 . Playing career . Junior hockey . Gilmour started playing junior hockey for the Cornwall Royals of the OHL in the 1980 – 81 season . He spent three seasons with the team , helping the team two consecutive Memorial Cup championships . He was injured during the 1981 championship run , but in the 1981 – 82 season , he returned to score 46 goals and 119 points . Gilmour was not drafted in his first year of NHL eligibility , but in the 1982 NHL Entry Draft , the St . Louis Blues drafted him in the 7th round , 134th overall . He did not make the Blues for the 1982 – 83 season , and was returned to Cornwall . He won the Eddie Powers Memorial Trophy as the leading scorer in the OHL with 70 goals and 177 points . He was also named OHL MVP . During the season he set a league record with a 55 game scoring streak . Professional career . St . Louis . Gilmour had difficulty reaching a contract with the Blues , who were still concerned that he was undersized for the NHL game . He almost resorted to playing professional hockey in Germany . Two weeks before the 1983 – 84 NHL season started , Gilmour and the Blues agreed on a contract and he joined the team . Injuries allowed him to play in the fourth line center slot , and he became a defensive specialist . Teammate Brian Sutter nicknamed him " Killer " because of his intensity on the ice , and name similarity to convicted killer Gary Gilmore . The nickname is also reported to stem from his resemblance to Charles Manson . During his first three seasons with the Blues , Gilmour was a consistent defensive presence who averaged 50 points . In the 1986 playoffs , he broke out and scored 21 points in 19 games , as the Blues lost in the Conference finals . This made Gilmour one of the only players in history to lead in postseason scoring without making it to the Stanley Cup Finals ; Peter Forsberg would also achieve that feat in 1999 with the Colorado Avalanche . Just prior to the 1988 – 89 season , Gilmour was traded to the Calgary Flames along with Mark Hunter , Steve Bozek , and Michael Dark for Mike Bullard , Craig Coxe and Tim Cokery . The Blues traded Gilmour after he was named in a civil suit alleging sexual improprieties with a teenaged babysitter . Gilmour denied that the incident occurred , and a grand jury did not find enough evidence to indict him . The Blues didn ' t admit publicly that the pending lawsuit against Gilmour was a reason for the trade , but Gilmour was convinced it was the reason : Calgary . With Calgary , Gilmour went on to win a Stanley Cup with the Flames in 1989 . Before the decisive game six of the series , he kissed and shook hands with Hockey Night in Canada commentator Don Cherry for good luck ; Cherry , who also hails from Kingston , affectionately called his favourite player " Dougie " . Gilmour netted the championship - winning goal against the Montreal Canadiens . Toronto . Several months after the Toronto Maple Leafs hired Cliff Fletcher to be their new general manager , he made a blockbuster trade with Calgary in February 1992 . Fletcher had previously served as Calgary ' s general manager before coming to Toronto , and he was responsible for putting together their 1989 championship team . The Leafs acquired Gilmour along with Jamie Macoun , Ric Nattress , Kent Manderville , and Rick Wamsley in exchange for Gary Leeman , Alexander Godynyuk , Jeff Reese , Michel Petit and Craig Berube . The 10 player deal was the largest in NHL history , and statistically speaking , one of the most lopsided . Toronto fans did not need to wait long for the Gilmour acquisition to pay off , as the feisty forward produced well for the remainder of the 1991 – 92 season . He then went on to have a breakout year , scoring a franchise - record 127 points during the 1992 – 93 regular season . In the playoffs , he played a key role as the Leafs took out the powerhouse Detroit Red Wings and St . Louis Blues , both in seven games . Gilmour finished the postseason with 35 points , behind only Wayne Gretzky . Gilmour was the runner - up for the Hart Trophy as regular - season MVP and won the Selke Trophy as best defensive forward , the first major NHL award that a Leaf player had won since 1967 . One of Gilmour ' s most memorable goals was scored during the 1993 second round playoffs series against the St . Louis Blues , in the second sudden death overtime period . Many fans remember him skating back and forth behind the St . Louis net multiple times before finally sliding the puck behind a sprawling Curtis Joseph , the latter who would also become famous with the Leafs years later . The Maple Leafs would go on to win the series , but would eventually be eliminated in the next round by Wayne Gretzky and the Los Angeles Kings . Toronto was leading the Conference series against Los Angeles 3 - 2 and many fans , including CBC ' s Don Cherry , were hoping for an all - Canadian final as the Montreal Canadiens already advanced . However , during overtime of game six , Gretzky high - sticked Gilmour , drawing blood without being assessed a penalty by the referee , Kerry Fraser , and then scored the winning goal moments later to stave off elimination which ignited the ' 100th Stanley Cup Controversy ' During game seven back at Maple Leaf Gardens , the Leafs were trailing 5 - 3 after Gretzky completed his hat - trick . Gilmour ' s team would score one goal but couldn ' t find the equalizer , which sent the Kings to the finals . Gilmour finished the 1993 – 94 season fourth overall in regular season scoring with 111 points , just one behind third place finisher Adam Oates . Gilmour made his second consecutive trip to the NHL All - Star game and finished as runner - up for the Selke Trophy . In the playoffs , he led his Leafs to the Western Conference Finals ( formerly Clarence Campbell conference ) , although they fell to the Vancouver Canucks in five games . The Leafs were the only team in the NHL to reach back - to - back conference finals over the 1992 – 93 and 1993 – 94 seasons . Over the course of the 1992 – 93 season and the 1993 – 94 season , only Oates scored more points than Gilmour . When the Leafs traded captain and fan favourite Wendel Clark to the Quebec Nordiques in the off - season of 1994 , Gilmour was named team captain . Throughout his six years as a Leaf , he was one of the most popular players on the team and in the league . He was a fan and media darling , as the spokesman for the NHLPA in community and charity events , and he also appeared in a series of memorable " Got Milk ? " TV commercials , one which also featured his wife . Later career . Fletcher traded Gilmour to the New Jersey Devils in 1997 for Steve Sullivan , Alyn McCauley and Jason Smith . Gilmour was their best postseason performer but the Devils suffered early exits in the playoffs . In the summer of 1998 Gilmour signed as a free agent with the Chicago Blackhawks . Chicago was Toronto ' s opposition on the night of the last game in historic Maple Leaf Gardens . Gilmour ended up scoring in that game and in the closing ceremonies , he was given a standing ovation by the Toronto fans . In spring of 2000 , Gilmour was traded to the Buffalo Sabres . He made an immediate impact with the struggling team , which had been Stanley Cup finalists the past season , helping them to make the playoffs . However , he was felled by stomach flu and only played in five playoff games . In 2000 – 01 , injuries limited Gilmour ' s regular season stats but he had a strong playoff performance as the rejuvenated Sabres beat the Philadelphia Flyers in the first round , although they were upset by the Pittsburgh Penguins in a tough second - round series . Gilmour , a well - traveled player by this time , then signed as a free agent in 2001 with the Montreal Canadiens , where he would fill a much needed role as a veteran leader . Gilmour had a good playoff run with the Canadiens but it was cut short by the Carolina Hurricanes . Notably before a playoff game , Gilmour also taped a message to Habs fans not to boo the US national anthem . Rumours floated around the hockey world that Gilmour was considering retirement . To the delight of Maple Leaf fans , the 2003 NHL trade deadline brought good news : the Canadiens traded Gilmour to the Maple Leafs for a sixth round draft pick so that he could finish his career in Toronto . Unfortunately , he suffered a knee injury in the second period of his first game back on March 13 against the Calgary Flames , and never played again . He officially announced his retirement on September 8 , 2003 after John Ferguson , Jr . declined to re - sign him . Gilmour had 450 goals and 964 assists in 1474 games in his NHL career . He remains eligible for induction into the Hockey Hall of Fame in 2009 . On September 15 , 2006 the Maple leafs announced that Gilmour would become their player development advisor . On August 7 , 2008 the Maple Leafs announced that Gilmour would become an assistant coach for the Leafs American Hockey League farm team , the Toronto Marlies . On November 17 , 2008 Gilmour left the Marlies to take over the head coaching position with the Kingston Frontenacs of the OHL . On January 31 , 2009 Gilmour ' s number 93 was honored by the Toronto Maple Leafs . Gilmour became the seventeenth player to be honored by the Maple Leafs .