As if playing for the Canadiens as a native Montrealer isn’t pressure enough, imagine doing so as the Rocket’s kid brother! Unfazed, Henri “The Pocket Rocket” Richard responded by simply playing more games with the Canadiens than any other player in team history and of course winning a truckload of Stanley Cups.

Richard’s first season with the Habs would prove to be a sign of things to come as he won the Stanley Cup in 1956. It marked the beginning of a Canadiens dynasty that would see Montreal roll to a league-record five straight championships. No other player boasts more than the 11 Cups the lifelong Canadien would pile up over his 20-year NHL career.

While his brother was among the game’s most prolific goal scorers of all-time, Richard emerged as one of hockey’s top playmakers. The tenacious 5-foot-7 centreman led the league in assists in both 1957-58 and 1962-63, but that is not to say he didn’t score big goals during his all-star career. Richard is one of the few players to have, not one, but two Stanley Cup winning goals on his resume. After notching the Game 6 overtime clincher that sank the Red Wings in 1966, he also scored winner in Game 7 of the 1971 final versus the Blackhawks.

The Habs 17th captain proudly wore the “C” from 1971 through his retirement in the spring of 1975, when Richard also received the Bill Masterton Trophy for his perseverance and dedication to the game. The Canadiens then immortalized his No. 16 on Dec. 10, 1975, as it joined his brother’s No. 9 high above the Forum ice. Richard was then reunited with the Rocket one more time upon his induction to the Hockey Hall of Fame in 1979.