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By: Ryan Gagne | Follow Me On Twitter @keepingthestats

As the first American-born franchise in NHL history, some of the game’s greatest players have worn a Boston Bruins jersey. Whether these skaters turned into Hall of Famers or were lucky enough to play in a few games, the Bruins have a tradition of winning, and their results at the annual NHL Awards show speak for themselves. 

Considering that some 2022-23 Bruins like Linus Ullmark, David Pastrnak, and Jim Montgomery are nominated for some hardware this spring, it was time to dig through the archives. Ultimately, we wanted to know which player has won the most trophies while representing Boston. Even though the top answer was obvious, we needed to know who else was on the list. 

Cecil Ralph “Tiny” Thompson – 4

Awards: Vezina (4) 

During the first ten years of his career, Tiny Thompson missed just one game, dressing in 463 games for the Bruins from 1928 to 1938. Ultimately, his success between the pipes led to four Vezina Trophy wins in 1930, 1933, 1936, and 1938.

Besides winning the Stanley Cup in 1929, he posted an astronomical 1.99 goals-against average (GAA) during that span, playing in an additional 33 playoff games. Impressively, his numbers were better in the postseason, where he had a 1.72 GAA. Eventually, Thompson went into the Hockey Hall of Fame (HHOF) in 1959.

Tim Thomas – 4

Awards: Vezina (2), Conn Smythe, and William M. Jennings

Tim Thomas took one of the longest roads to NHL superstardom, making his debut in 2002, eight years after being drafted by the Quebec Nordiques in the ninth round in 1994. After bouncing around the globe playing professional hockey, he eventually became a Bruins regular in 2005, suiting up for 38 games. 

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Ultimately, within seven years, he would become one of the game’s best netminders, winning two Vezina Trophies (2009, 2011) while capturing the William M. Jennings Trophy in 2009. Despite the individual success, Thomas’ crowning achievement occurred in 2011 when he led Boston to a Stanley Cup championship winning the Conn Smythe Trophy. Statistically, his performance that year remains one of the best. 

Eddie Shore – 4

Awards: Hart Memorial (4)

Outside of ten games played with the New York Americans in 1939-40, Eddie Shore was a Bruin for life, playing 541 games over 14 years in black and gold. Interestingly, he spent the first part of his career averaging 137 penalty minutes a season before changing his style resulting in four Hart Trophy wins. 

Statistically, he was an eight-time All-Star, the same number of times he finished in the top five for Hart Trophy voting. Historically, Shore was a member of the Bruins’ first two Stanley Cup titles in 1929 and 1939, earning enshrinement at the HHOF in 1947. 

Ray Bourque – 7

Awards: James Norris Memorial (5), Calder Memorial, and King Clancy

Historically, many would argue that Ray Bourque is one of the top ten, if not top five, defensemen to ever play in the NHL. Although he only won the Norris Trophy five times (1987, 1988, 1990, 1991, and 1994), he ranks as the 11th highest-scorer in league history with 1,579 points. 

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Ultimately, Bruins fans knew great things were in store for the franchise’s longest-serving captain when he won the Calder Memorial Trophy as a rookie in 1980. Besides winning the King Clancy Memorial Trophy in 1992, he led the Bruins to the Stanley Cup Final in 1988 and 1990. Although he would win the game’s biggest prize on another team (Colorado Avalanche), Bourque was a first-ballot Hall of Famer in 2004. 

Patrice Bergeron – 8

Awards: Frank J. Selke (5), King Clancy, NHL Foundation Player, and Mark Messier NHL Leadership

Patrice Bergeron has spent his entire career in Boston, serving as the team’s captain, an honor bestowed upon him in 2020. Although his future remains uncertain, the long-term Bruin can rest assured when he retires; his number 37 will go to the TD Garden rafters.

Realistically, when Bergeron hangs them up, he’ll be another first-ballot Hall of Famer thanks to a record five Frank. J. Selke Trophy wins (2012, 2014, 2015, 2017, and 2022). Besides being the league’s top defensive forward, he also won the King Clancy Memorial Trophy (2013) and the Mark Messier NHL Leadership Award in 2021. 

Phil Esposito – 9

Awards: Art Ross (5), Hart Memorial (2), and Ted Lindsay (2)

Even though Phil Esposito played with other franchises (New York Rangers and Chicago Blackhawks), his outstanding career totals will always be associated with Boston, where he found his biggest success. Statistically, outside of Gordie Howe’s career totals, he retired as one of the top goal-scorers and point collectors in NHL history. 

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Within a year of coming to the Bruins in 1967, Esposito would win his first of five scoring titles (1969, 1971, 1972, 1973, and 1974) and the first of his two MVP awards (1969 and 1974). Additionally, he won two Stanley Cups in 1970 and 1972 and two Ted Lindsay Awards in 1971 and 1974. During his time with the Bruins, the future Hall of Famer (1984) would set a new NHL record for points in a season with 152 in 1971, a mark that stood for ten seasons. 

Bobby Orr – 17

Awards: James Norris Memorial (8), Hart Memorial (3), Conn Smythe (2), Art Ross (2), Calder Memorial, and Ted Lindsay

One of the most significant debates in hockey revolves around whether or not Bobby Orr is the greatest player of all time. Although each side presents a compelling case, one thing is sure: he is the best defender to play professional hockey.  

Ultimately, Orr changed the game with his style of play, rushing end to end to score goals and win scoring titles. Besides Wayne Gretzky’s record nine Hart Trophy wins, the Bruins’ defenseman stands alone at the top of the Norris Trophy winners list with eight straight victories from 1968 to 1975. 

Considering Orr scored the most iconic goal ever captured on film, it is no surprise he won the Conn Smythe Trophy when the Bruins won the Stanley Cup in 1970 and 1972. Additionally, he won two scoring titles (1970 and 1972) and three straight league MVP awards from 1970 to 1972. 

Unfortunately, he retired at 30, citing knee problems. However, that didn’t stop the former Rookie of the Year (1968) from being voted the MVP by his peers in his final full season in 1975. 

The Rest of the Pack

Surprisingly, the Bruins are one of only two teams in NHL history to have over 90 players win individual awards, trailing the Montreal Canadiens with a record of 119 victories. Statistically, the Detroit Red Wings are in a distant third place with 77 wins, meaning Boston will be locked in this spot for years. 

Interestingly, outside of the players on this list, only four players in team history have won a trophy on three separate occasions: John Bucyk, Bobby Bauer, Frank Brimsek, and Bill Cowley. Outside of those names, only five players have taken home two pieces of hardware: Milt Schmidt, Zdeno Chara, Tuukka Rask, and Joe Thornton. Of course, Thornton’s win has an asterisk next to it since he was with the San Jose Sharks at the time of the success. However, the Bruins’ record book still includes his name since he was their captain at the beginning of his winning season.

Considering Boston just had the best regular season in NHL history, it wouldn’t surprise anyone if the list of Bruins’ trophy winners expands at the 2023 NHL Award Show.Ā