No man has embodied the captaincy in Boston like Raymond Bourque. The C adorned Bourque's jersey from 1985 to 2000, making him the longest-tenured captain in Bruins history.
Bourque won the Norris Trophy five times in that span, racking up more points than any defenseman in NHL history.
He was the face of the Bruins for two decades. However, he failed to win the Stanley Cup in Boston.
In 2000, the Bruins showed their immense respect for Bourque by trading him to the Colorado Avalanche, with whom he would finally hoist the trophy that eluded him for more than 20 years.
Bourque, fittingly, brought the Cup to Boston for an emotional rally.
The quintessential Bruin was never blessed with the same kind of surrounding talent as the others on this list, but he still managed to leave an unmatched impact.
Bourque's No. 77 is the most recent to be retired in Boston, and the legendary defenseman was inducted into the Hall of Fame in 2004.