The last time the Boston Bruins and Detroit Red Wings met in the playoffs was WAY back in 1957! Boston would win that semi-final 4 games to 1 and advanced to the Stanley Cup finals, only to lose to Montreal.
Both Boston and Detroit were headed for long droughts of hockey success. The Bruins would soon struggle until the arrival of Bobby Orr a decade later. The Red Wings would struggle more or less for the next 35 years before finally finding success in the 1990s and beyond.
That 1957 Detroit team was looking for some new blood to resuscitate the great Wings teams of the early 1950s. They had one great young player of note just breaking into the lineup, but they ended up trading the future Hockey Hall of Famer away. That youngster was Johnny Bucyk, and he became the leader of the Boston Bruins for the next 20 seasons.
One can not help but wonder how much better the Red Wings could have been with Bucyk on Gordie Howe's left wing during the 1960s. After all, Bucyk went on to become (and still remains) Boston's all-time leader in seasons (21), games (1,436), and goals (545).