Bruins & Maple Leafs Original Six Era Trade History

In 1917 the National Hockey League (NHL) came into existence with four teams, the Montreal Canadiens, the Toronto Hockey Club, the Ottawa Senators, and the Montreal Wanderers. Within seven seasons, the league expanded into the United States when the Boston Bruins were born on Nov. 1, 1924.

By that time, the Toronto franchise had gone from being called the Toronto Arenas to the Toronto St. Patricks’ (Pats) before settling on the iconic Maple Leafs name we are all familiar with today. Conversely, the Bruins have kept their name, despite altering their logo and colors at least once in the last 98 years.

Together the Bruins and Maple Leafs have one of the league’s longest rivalries, dating back almost a century, with the most recent chapter centered around playoff heartbreak. Indeed, these two franchises are among the league’s most respected clubs. Furthermore, it is a dream and a privilege for some players to suit up for either franchise, so imagine achieving that goal and then being traded from one team to another.

Historically, these two teams have executed 39 trades over a century of hockey. In the beginning, between 1924 and 1937, there were 11 transactions, with the bulk of the dealings involving a player for cash. Then, during the Original Six era (1942-1967), there were 14 trades involving a handful of Hall of Famers and multi-time Stanley Cup Winners. Finally, since the birth of the Expansion Era, which has seen the league grow to 32 teams, the B’s and Leafs have swapped players in 14 dealings.

Although the two teams have been quiet with no transactions since 2011, we’d be hard-pressed not to remember that the most important deals have all occurred since the turn of the century. Considering how much coverage these trades have had, it was time to look at a different era and dig deep into the top 5 transactions that altered both clubs during the Original Six period.

Bruins Trade Murray Oliver and Cash to Maple Leafs for Eddie Shack (May 15, 1967)

In 1957 Eddie Shack made his NHL debut with the New York Rangers, where the Sudbury, Ontario native played two and half years before a trade to the Maple Leafs in 1960. Within two seasons, he won his first Stanley Cup title and finished his stint with the club as a four-time champion by 1967. Statistically, Shack suited up for 504 games in the north and registered 195 points before the Bruins acquired him in 1967 for Murray Oliver and some cash.

Conversely, Oliver came into the league during the 1957-58 season with the Detroit Red Wings before joining the Bruins in 1960, where he collected 332 points in 429 games. After seven seasons, he departed to head north and played 226 games with the Maples Leafs, registering 134 points. Meanwhile, Shack’s time in Boston was short-lived (two seasons), where he played 141 games and mustered up just 42 points.

Bruins Trade Andy Hebenton, Orland Kurtenbach, and Pat Stapleton to Maple Leafs for Ron Stewart (June 8, 1965)

On a summer day in June 1965, the Maple Leafs orchestrated a deal for one of their most veteran players and three-time Stanley Cup champion Ron Stewart. After 13 seasons, 838 games, and 368 points, he headed to the Bruins, only to play two seasons with the club, adding 60 points to his resume.

The trade package included three players going north: Andy Hebenton, Orland Kurtenbach, and Pat Stapleton. After the ink dried on the papers, only Kurtenbach suited up for the Maple Leafs, collecting 15 points in 70 games. Although the trio played 302 contests with the Bruins, they were not part of Toronto’s plans after the deal.

Bruins Trade Allan Stanley to Maple Leafs for Jim Morrison (Oct. 8, 1958)

Jim Morrison is among the few players to be traded back and forth between the same two teams. After making his professional debut with the B’s in 1951-52 and skating in 14 games, a trade in January 1952 sent him to the Maple Leafs. There, Morrison played 399 games in blue over seven seasons before another deal in 1958 brought him back to Boston.

The other player in the transaction, Allan Stanley, made his NHL debut in 1948-49 with the New York Rangers. After six and half seasons in the Big Apple, he played one season with the Chicago Blackhawks before landing with the Bruins for the 1956-57 season. The future Hall of Famer would only play 129 games and tally 62 points in black and gold; however, he would turn into a three-time All-Star in Canada. After settling in with the Maple Leafs, he would capture three Stanley Cups championships with 233 points in 633 games.

Bruins Trade Joe Klukay to Maple Leafs for Leo Boivin (Nov. 9, 1954)

This 1954 trade needs to be clarified, so let’s iron out the finer details. Joe Klukay began his NHL career with the Maple Leafs in 1942-43 and won four Stanley Cup championships across six seasons. Nevertheless, after 153 points in 342 games, he made his way to Boston in a 1952 trade for cash.

Eventually, the B’s traded him back to Toronto after 150 games (66 points) in exchange for future Hall of Famer Leo Boivin. At the time, Boivin had been a professional hockey player for just 137 games, collecting 23 points. Nonetheless, after the transaction, he suited up for 717 games with the Bruins before finishing his career on a handful of expansion clubs. Meanwhile, Klukay played two more seasons with the Maple Leafs before retiring in 1956.

Bruins Trade Art Jackson to Maple Leafs for Bingo Kampman and cash (Dec. 24, 1944)

The Original Six era began in 1942, and these two franchises didn’t wait long to strike a deal. On Christmas Eve in 1944, the Bruins traded away Art Jackson, a 1941 Stanley Cup-winning team member, returning him to the team he broke into the league with, the Maple Leafs.

He made his NHL debut with Toronto in 1934 and played three seasons with the team before a cash trade brought him to Boston. Even though Jackson’s stint with the Bruins was separated by a year with the New York Americans, he played a total of 308 games, tallying 228 points over seven seasons.

Then, in 1944, Jackson returned to Toronto in exchange for Bingo Kampman, a member of the 1942 Stanley Cup-winning team who never played in the NHL after that season. Although still playing professionally, Kampman never suited up for the Bruins, while Jackson would win another championship in 1945, retiring shortly after popping champagne.

Honorable Mention: The Two Fern Flaman Trades (1950, 1954)

Fern Flaman was a member of the Maple Leafs who won the 1952 Stanley Cup championship and was a 1990 inductee into the Hockey Hall of Fame. However, he only played with two franchises, the Bruins and Maple Leafs, having been traded once from each club.

At 18 years old, after making his debut in Boston during the 1944-45 campaign, he played parts of six and half seasons before a trade sent him to the Maple Leafs in 1950. Next, the Bruins dealt Flaman, along with Boivin, Phil Maloney, and Ken Smith, for Bill Ezinicki and Vic Lynn. Moreover, Flaman would win a championship in 1952 and suit up for parts of four seasons before returning to the B’s in 1954 for Dave Creighton.

Ultimately, Flaman was the most accomplished player in both transactions, finishing his career with 208 points in 911 games. Although, a handful of other players like Boivin (HHOF) and Lynn (three Stanley Cups) found success on various levels.

Looking Back at Historical Trades

Whenever we look back at trades, whether they were historical blockbusters like Andrew Raycroft for Tuukka Rask or more simple ones like Ernie Parks for cash in 1924, there are always various ways to dissect who the actual winner is. However, since most of these trades took place half a century ago, it is relatively simple to see which team walked away with the better deal.

In an era with limited trading partners, the Bruins and Maple Leafs made 14 deals involving several Hall of Famers and Stanley Cup champions. At the time, some of these moves altered lineups and shook up dressing room chemistry. Furthermore, since these teams played more frequently, the animosity between players came easily, especially for old teammates who now faced each other.

The Bruins and Maple Leafs have a long history of intense battles on the ice, and despite sharing a lineage by being division and conference rivals, they are still willing to make a deal with one another. Although not every trade is a headline grabber or franchise-altering, a trade is a trade, and the effects can have ramifications decades later.