When the Western Hockey League folded after the 1925-26 WHL season, a deal was made so that two of the most successful of the teams in that league, the 1925 Stanley Cup champion Victoria Cougars, and the Portland Rosebuds (to become the Chicago Blackhawks) would jump to the NHL. The Victoria Cougars were originally called the Victoria Aristocrats and belonged to the Pacific Coast Hockey Association, which folded and then merged with the Western Canada Hockey League for the 1924-25 WCHL season. Since no arena in the Motor City was ready at the time, the newly-renamed Detroit Cougars played their first season in Windsor, Ontario. For the 1927-28 season, the Cougars moved into the new Detroit Olympia, which would be their home rink until December 15, 1979. This was also the first season behind the bench for Jack Adams, who would be the face of the franchise for the next 36 years as either coach or general manager.

In 1930 the Cougars were renamed the Falcons, but their woes continued, usually finishing near the bottom of the standings. When James Norris Sr. bought the team in 1932 the team was renamed the Detroit Red Wings. Earlier in the century, Norris had played on one of hockey's early powers, the Montreal Amateur Athletic Association, nicknamed the "Winged Wheelers." Because of the team’s location in Detroit, the Motor City, Norris transformed the MAAA logo into the first version of the Red Wings logo as we know it today. He also gave Adams a year on his job on probation and a handshake. Their first year with the current name they won their first playoff series in the NHL, over the now-defunct Montreal Maroons. They lost in the semi-finals against the New York Rangers.

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The Wings struggled and finished last the following season. They regrouped and made the playoffs again the following year, and made the Stanley Cup Finals in three consecutive years during the early 1940s. In 1941 they were swept by the Boston Bruins, in 1942 they blew a three-game lead against Toronto to lose the finals, but in 1943, with Syd Howe and Mud Bruneteau scoring 20 goals apiece, Detroit won their third Cup by sweeping the Bruins. They remained a solid team through the rest of the decade, making the playoffs every year, and reaching the finals three more times.

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After being upset by the Montreal Canadiens in the 1951 semifinals, Detroit won its fifth Cup in 1952, with the Production Line of Howe, Abel and Lindsay joined by second-year goalie Terry Sawchuk. Abel left the Wings for Chicago following the season, and his spot on the roster was replaced by Alex Delvecchio. The 1952 playoffs featured the start of a Red Wings tradition - the octopus throw. The owner of a local fish market threw one from the stands and onto the ice. The eight legs were symbolic of the eight playoff wins it took to win the Stanley Cup at the time. They swept both of their opponents that year. 1952 also saw the passing of James Norris Sr., with his daughter Margurite becoming President and Governor of the Red Wings.

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Following another playoff upset in 1953 at the hands of the Bruins, the Red Wings won back to back Stanley Cups in 1954 (over Montreal, when Habs defenseman Doug Harvey redirected a Tony Leswick shot into his own net) and 1955 (also over Montreal in seven games). Also during 1955 off-season, Margurite Norris was forced to turn the team over to younger brother Bruce. Detroit and Montreal once again met in the 1956 finals, but this time the Canadiens won the cup, their first of five in a row. In 1957 Ted Lindsay, who scored 30 goals and led the league in assists that year, helped start the NHLPA and was promptly traded. The Wings lost in the first round of the playoffs to the Bruins. In 1959 the Red Wings missed the playoffs for the first time in 21 years.

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Adams was fired as general manager in 1963. By the late 1960s, the Wings started to flounder and entered a funk that they wouldn't get out of for almost 20 years. Between 1967 and 1983, Detroit only made the playoffs twice, winning one series. The legendary Gordie Howe retired in 1971. Howe returned to pro hockey shorty after to play with his two sons Mark and Marty Howe. (Mark would later join the Red Wings at the end of his career)Detroit lost Howe to the upstart World Hockey Association in 1972. Through the decade, with Mickey Redmond having two 50-goal seasons and Marcel Dionne starting to reach his prime (which he didn't attain until he was traded to the Los Angeles Kings), a lack of defensive and goaltending ability continually hampered the Wings.

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In 1989, Yzerman scored a career-best 65 goals, but Detroit was upset in the first round by the Blackhawks. The following season Yzerman knotted 62 goals but the team didn't even make the playoffs. Demers was fired, and the Red Wings haven't missed the playoffs since. Yzerman was joined by Sergei Fedorov (who defected from the USSR) and enforcer Bob Probert, two of the most familiar faces of the Wings in the 1990s. In 1992 the team acquired Ray Sheppard, who had a career-best 52 goals two years later; and top defenseman Paul Coffey. Also joining the Red Wings around this time were draft picks like Slava Kozlov, Darren McCarty, Vladimir Konstantinov, and Nicklas Lidström.

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Tragedy struck the Wings days after their championship. Vladimir Konstantinov suffered a brain injury in a car accident, and his career had to come to an abrupt end. Their 1997-98 season, which also ended in a Cup victory (a sweep over the Washington Capitals), was dedicated to Konstantinov, who came out in his wheelchair that night to touch the Cup. The Wings built up a fierce rivalry with the Avalanche by this time. With the Red Wings beating the Avalanche in the third round in 1997, and Colorado beating Detroit in the second round in both 1999 and 2000, the battles between these two teams has become one of the fiercest in sports. During one game, a brawl ensued between Colorado goalie Patrick Roy and his Detroit counterpart Mike Vernon and Darren McCarty paid back Colorado's Claude Lemieux for his hit on Kris Draper the year before. That hit forced Draper to get reconstructive surgery on his face.

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Longtime Red Wing Sergei Fedorov signed with the Mighty Ducks as a free agent during the offseason. Hasek came out of retirement, and joined the Wings for the 2003-04 season. This meant that Detroit had three goalies, with Joseph and Manny Legace as backups. The Wings also added defenseman Derian Hatcher from Dallas via free agency, as well as forward Ray Whitney from Columbus as a free agent. Joseph, despite being one of the highest paid players in the NHL, had to spend part of the season with the Grand Rapids Griffins, Detroit's American Hockey League affiliate. Ultimately, Hasek had to call it quits because of a groin injury, and Joseph led the team to the top of the Central Division and the Western Conference. Hatcher was also injured just a few games into the regular season with a torn MCL. He would not return until the end of the regular season. The Wings acquired veteran center Robert Lang from the Capitals at the trade deadline and he made a big impression over the next few weeks.

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