Last in the series. I'll start with the 1926-27 season. Partly because most of the previous winning coaches were player-coaches. Partly because it was the first season in which the Stanley Cup became the sole province of the National Hockey League. And partly because it was the first season for 3 of the modern teams: The New York Rangers (who, in those pre-Devils days, did not suck), the Chicago Blackhawks and the Detroit Red Wings.
Remember: A player who didn't make it to the NHL, even if it was through no fault of his own (injury, illness, career interrupted by military service), is still classified as a "mediocre player."
1927 Ottawa Senators: Dave Gill. As far as I know, he never played pro hockey. This was the last of 9 Cups won by the old Senators, formerly known as the Ottawa Silver Seven. (There was an additional position 100 years ago, the "rover," sort of a half-forward, half-defenseman. Bobby Orr and Paul Coffey would have played the position.) These Senators went bankrupt in the Depression, moving to become the St. Louis Eagles in 1934 and folding a year later. The new Sens began in 1992, and have been far less successful: They're usually competitive, but they've won a grand total of 1 Stanley Cup Finals game.
1928 New York Rangers: Lester Patrick. One of the best defensemen of his time. In the Hockey Hall of Fame as a player, although he had much more influence as a coach and executive.
1929 Boston Bruins: Cy Denneny. One of the best forwards of his time. Hall of Fame.
1930 Montreal Canadiens: Cecil Hart. Never played.
1931 Canadiens: Hart.
1932 Toronto Maple Leafs: Dick Irvin. One of the best forwards of his time. Hall of Fame as a player, although he had much more influence as a coach. Actually, his best contribution to the game may have been his son, Hall of Fame broadcaster Dick Irvin Jr.
1933 Rangers: Patrick.
1934 Chicago Blackhawks: Tommy Gorman. Never played hockey, but was one of the best lacrosse players of his time.
1935 Montreal Maroons: Gorman. Not sure why he left the Hawks after winning the Cup, although it may have had something to do with team owner Frederic McLaughlin being a lunatic.
1936 Detroit Red Wings: Jack Adams. One of the best forwards of his time. In the Hockey Hall of Fame as a player, although he had much more influence as a coach and executive.
1937 Wings: Adams.
1938 Hawks: Bill Stewart. Played in college, but his professional sport was baseball. An injury cut short his playing career, but he became both a baseball umpire and a hockey referee, as well as the first American to coach a Cup winner.
1939 Bruins: Art Ross. One of the best defensemen of his time. In the Hockey Hall of Fame as a player, although he had much more influence as a coach and executive. You might be recognizing some of these names if you're a hockey fan over the age of 30, even if you're not one over the age of 80: Patrick, Ross and Adams all got their names put on NHL Divisions from 1974 to 1993, along with Toronto Maple Leafs executive Conn Smythe. With the NHL now having 6 Divisions, we'd probably have to add Scotty Bowman and Al Arbour.
1940 Rangers: Frank Boucher. Great center, on a line between the brothers Bill and Frederick "Bun" Cook, on the 1928 and '32 Cup-winning Rangers. Patrick, by now, was "only" the general manager, although his sons Lynn and Murray "Muzz" Patrick were Ranger players. Boucher, a Hall-of-Famer, was a part of every Ranger Cup-winner until 1994. And yet they've never retired his Number 7. Okay, it was also Rod Gilbert's number, but they've retired 9 for both Andy Bathgate and Adam Graves.
1941 Bruins: Ralph "Cooney" Weiland. Like Patrick, Ross left coaching and stayed the GM, and promoted his former Number 7, a Hall of Fame forward.
1942 Leafs: Clarence "Happy" or "Hap" Day. A Hall of Fame defenseman for the Leafs.
1943 Wings: Adams.
1944 Canadiens: Irvin. Left the Leafs for their arch-rivals. And, yes, today, the Habs and Leafs are still each others' arch-rivals, no matter what fans of the Bruins and the revived Ottawa Senators might think.
1945 Leafs: Day.
1946 Canadiens: Irvin.
1947 Leafs: Day.
1948 Leafs: Day.
1949 Leafs: Day.
1950 Wings: Tommy Ivan. An injury kept him from reaching the NHL.
1951 Leafs: Joe Primeau. A Hall of Fame center with the Leafs, along with Charlie Conacher and Harvey "Busher" Jackson on the 1930s' "Kid Line."
1952 Wings: Ivan.
1953 Canadiens: Irvin.
1954 Wings: Ivan.
1955 Wings: Jimmy Skinner. In the modern NHL, he probably would have made it, but in the six-team era, his path was blocked.
1956 Canadiens: Hector "Toe" Blake. He and Elmer Lach flanked Maurice "the Rocket" Richard on the "Punch Line" in the 1940s. An injury cut short his playing career but he was still elected to the Hall. Irvin was, uh, eased out of the Habs' head job after the 1955 season, partly because it was thought that an ex-teammate and good friend like Blake could handle the Rocket better, following the riot that bears his name. Blake coached 8 Stanley Cup winners, a record until Scotty Bowman broke it.
1957 Canadiens: Blake.
1958 Canadiens: Blake.
1959 Canadiens: Blake.
1960 Canadiens: Blake.
1961 Hawks: Rudy Pilous. A prospect for the Rangers, he never reached the NHL.
1962 Leafs: George "Punch" Imlach. Played minor-league hockey in Toronto, went off to World War II, and was offered a tryout by the Wings after his discharged, but didn't think he was in shape, and went into coaching.
1963 Leafs: Imlach.
1964 Leafs: Imlach.
1965 Canadiens: Blake.
1966 Canadiens: Blake.
1967 Leafs: Imlach.
1968 Canadiens: Blake.
1969 Canadiens: Claude Ruel. Played for the Habs' junior teams, but never reached the big club.
1970 Bruins: Harry Sinden. A good minor-league player, and an Olympian, but never reached the NHL.
1971 Canadiens: Al MacNeil. A defenseman, probably the first on this list to be good but not great, his career didn't have a whole lot of luck. Played for the Leafs before they won their 1960s Cups, the Habs between their '60 and '65 Cups, and the Hawks after their '61 Cup. Also an original 1967-68 member of the Penguins. His rotten luck continued when he coached the Canadiens in the 1969-70 and 1970-71 seasons -- bracketing the October Crisis in Quebec. During the '71 Finals, with the Habs down 3 games to 2 to the Hawks, with a potential Game 7 in Chicago, Henri Richard, the Rocket's much younger brother but also a HOFer, told the French media in Montreal, "MacNeil est incompetent." These words, suggesting that MacNeil's inability to speak French left him unable to properly deal with the many players whose ethnicity and language got the team nicknamed "the Flying Frenchmen," stirred up the ethnic, linguistic and political emotions of a city that, without having a wall, was as much divided at the time as Berlin. The only thing that could unite the city was the Canadiens, and they won Game 6 at home and Game 7 on the road. Afterward, Henri said, "I should've kept my mouth shut." As with Irvin in '55, MacNeil was quietly offered another place in the organization, and in came Scotty Bowman, who had coached the St. Louis Blues to the Finals in their first 3 seasons of play, without winning a Finals game, getting swept by the Habs in '68 and '69 and the Bruins in '70, despite a veteran lineup. Bowman and the '70s Habs were on their way to becoming the best dynasty in the game's history, as players like Henri and Jean Beliveau were on their way out, while men like Guy Lafleur, Larry Robinson and Ken Dryden were on their way in. MacNeil did coach in the NHL again, leading the Flames in 1980 when they moved from Atlanta to Calgary.
1972 Bruins: Tom Johnson. A Hall of Fame defenseman on the 1950s Canadiens.
1973 Canadiens: Scotty Bowman. An injury cut short his playing career, but as a coach he won a record 9 Cups, and with 3 different teams, so it can't be said that he was solely a beneficiary of the Habs' wonderful scouting and minor-league system. He is now a senior adviser to the Blackhawks, and his son Stan is their GM, and thus, as of 2010, also a Cup winner.
1974 Philadelphia Flyers: Fred Shero. The first first-time winners of the Cup in 38 years were coached by Freddy the Fog, who briefly played for the Rangers but was basically a career minor-leaguer.
1975 Flyers: Shero.
1976 Canadiens: Bowman.
1977 Canadiens: Bowman.
1978 Canadiens: Bowman.
1979 Canadiens: Bowman.
1980 New York Islanders: Al Arbour. An All-Star defenseman, won Cups with the '54 Wings, the '61 Hawks and the '62, '63 and '64 Leafs. Also a member of the Finalist Blues under Bowman, alongside such NHL legends as Jacques Plante and Doug Harvey. That Blues team thus had a reach in the NHL into the early Fifties and into the 21st Century. In the Hall as a "Builder," which is the Hall's category for coaches and executives, but a pretty good player.
1981 Isles: Arbour.
1982 Isles: Arbour.
1983 Isles: Arbour.
1984 Edmonton Oilers: Glen Sather. A defenseman, was traded from the Bruins right before their '70 Cup and the Habs right before their '76 Cup began a string of 4 straight. But his luck evened out as a coach.
1985 Oilers: Sather.
1986 Canadiens: Jean Perron. Never played in the NHL.
1987 Oilers: Sather.
1988 Oilers: Sather.
1989 Flames: Terry Crisp. A good center for the '74 & '75 Broad Street Bullies, although not, himself, known as a dirty player.
1990 Oilers: John Muckler. Never played in the NHL.
1991 Pittsburgh Penguins: Bob Johnson. Longtime head coach at the University of Wisconsin, earning him the name "Badger Bob," he produced some of the players on the 1980 U.S. Olympic team, including their leading scorer, his son Mark Johnson. But he never played in the NHL. Died of cancer shortly after winning the '91 Cup. The Pens then hired Bowman, in the hope that he could keep the team's newfound success going. He did.
1992 Pens: Bowman.
1993 Canadiens: Jacques Demers. Never played in the NHL.
1994 Rangers: Mike Keenan. Although he's coached 8 different teams, including taking the Flyers to the '85 and '87 Finals and in '94 becoming the only living person to coach the Rangers to a Cup, he never played in the NHL.
1995 New Jersey Devils: Jacques Lemaire. A Hall of Fame forward for the 1970s Habs, he scored the goal that won Game 4 of the '77 Finals and gave Montreal a sweep of the Bruins -- as reflected in the film of Barney's Version. (While the Mordecai Richler novel on which it's based has Barney as a huge Habs fan, the time periods are different, so Lemaire's goal does not, as in the film, happen on the day of his 2nd wedding.)
1996 Colorado Avalanche: Marc Crawford. An unremarkable player, although he did help the Vancouver Canucks reach their first Stanley Cup Finals, in 1982.
1997 Wings: Bowman.
1998 Wings: Bowman.
1999 Dallas Stars: Ken Hitchcock. Never played in the NHL. Now coaching the Blues.
2000 Devils: Larry Robinson. Hall of Fame defenseman for the 1970s and '80s Habs.
2001 Avs: Bob Hartley. Never played in the NHL. Not to be confused with the lead character on the 1970s sitcom The Bob Newhart Show.
2002 Wings: Bowman. His 9th and last.
2003 Devils: Pat Burns. Never played in the NHL.
2004 Tampa Bay Lightning: John Tortorella. A collegiate star, he never reached the NHL. Now the coach of the Rangers, who, as you may have noticed, suck.
2005 No Cup. Gary Bettman, you're going to hell, where you'll face Devils who will
treat you worse than the ones in New Jersey.
2006 Carolina Hurricanes: Peter Laviolette. Played a grand total of 12 games in the NHL, all in the 1988-89 season with the Rangers, who, by that point, had begun to suck. Now the coach of the Flyers -- who swallow.
2007 Anaheim Ducks: Randy Carlyle. An All-Star defenseman with the original Winnipeg Jets.
2008 Wings: Mike Babcock. Never played in the NHL.
2009 Pens: Dan Bylsma. Played several years as a defenseman with the two L.A.-area teams, the Kings and the Ducks.
2010 Hawks: Joel Quenneville. An original member of the Devils, was with the franchise when it moved from Denver, as the Colorado Rockies, in 1982. Being, as Wayne Gretzky put it, "a Mickey Mouse organization" at the time, they let him get away, and he became an All-Star defenseman with the Hartford Whalers.
2011 Bruins: Claude Julien. Had, as they would say in baseball, two "cups of coffee" with the Quebec Nordiques in the mid-1980s.
Great players: 29
Good players: 8
Mediocre players: 46
So there have been quite a few great players who've gone on to coach Stanley Cup winners. However, since Toe Blake hung up his whistle in 1968, of the 42 Cup-winning teams, 31 were led by mediocre players.
So my theory holds in this sport, too.
Today, the New Jersey Devils are coached by Peter DeBoer, who never played in the NHL. Does that mean there's hope for a Cup under him? If his coaching in this 2011-12 season thus far is any indication, the answer is no.