The Three Best Trades in Toronto Maple Leafs History

The Toronto Maple Leafs are one of the most storied franchises in the NHL. While the team has had its share of missteps in the trade department, some key deals have shaped the franchise’s future. These trades have brought in players who became icons in Toronto and left an indelible mark on the team’s history. In this post, I’ll look at the three most significant trades in the history of the Maple Leafs.

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The Maple Leafs Third-Best Trade: The Rick Vaive, Bill Derlago, and Tiger Williams Trade (1980)

In 1980, the Maple Leafs sent forward Dave “Tiger” Williams and Jerry Butler to the Vancouver Canucks. Coming back were Rick Vaive and Bill Derlago.

The most notable player to come out of this trade for Toronto was Rick Vaive. Vaive would become one of the best and most important players in the Maple Leafs’ history. He was the first player in franchise history to score 50 goals in a season (1982-83). As well, he developed into a key leader for the team throughout the 1980s. His scoring ability and physical play made him an immediate fan favorite, and his impact on the team was enormous.

Williams gained a reputation as one of the toughest players in the NHL. He was known for his gritty play and fighting skills. Still, Vaive’s offensive explosion became the cornerstone of this trade. His 50-goal seasons were a key factor in the Maple Leafs’ competitiveness during the early 1980s.

This trade had lasting ramifications for the Maple Leafs. It delivered the team its first 50-goal scorer and one of the most consistent offensive players in its history. Vaive’s tenure in Toronto elevated the team’s competitiveness in the 1980s and established him as one of the most important players in Maple Leafs’ history.

The Maple Leafs Second-Best Trade: The Mats Sundin Trade (1994)

In 1994, the Toronto Maple Leafs, under general manager Cliff Fletcher, acquired Mats Sundin from the Quebec Nordiques. In that trade, fan favorite Wendel Clark, Sylvain Lefebvre, and Landon Wilson moved to Quebec. Sundin became the face of the franchise for the next 13 years. Clark was beloved in Toronto, and his departure was painful for fans. However, the arrival of Sundin—who was just 23 then—proved to be a game-changer for the Maple Leafs.

Sundin became the first European-born captain in the franchise’s history. He held this distinction for the entirety of his time in Toronto. Over his tenure, Sundin set franchise records for goals, assists, and points. He became one of the most skilled players in the NHL. His leadership, both on and off the ice, was a guiding force for the team during the late 1990s and early 2000s.

Sundin’s best years in Toronto came during the late ’90s and early 2000s, when he led the team to several deep playoff runs, including a memorable trip to the 2002 Eastern Conference Finals. His accomplishments were impressive. He was selected to multiple All-Star Games and finished his career with over 500 goals and 700 assists, making him one of the most prolific players in franchise history.

The Sundin trade ranks one of the most significant in Maple Leafs history. It brought a Hall of Fame-caliber player and future team captain to the club. Sundin also helped solidify the Maple Leafs become a legitimate contender in the NHL for over a decade.

The Maple Leafs Best Trade: The Doug Gilmour Trade (1992)

On January 2, 1992, Cliff Fletcher pulled off one of the most impactful trades in franchise history. He acquired Doug Gilmour from the Calgary Flames in exchange for Gary Leeman, along with other players like Michel Petit, Alexander Godynyuk, and a draft pick.

Gilmour was a revelation. Arriving in Toronto, he immediately became the heart and soul of the team. In his first full season with the Maple Leafs, he won the Selke Trophy as the league’s best defensive forward. He set a franchise record with 127 points during the 1992-93 season. He also led the Maple Leafs to back-to-back appearances in the Eastern Conference Finals in 1993 and 1994. It was an incredible feat for a franchise that had been mired in mediocrity in the years.

Gilmour’s work ethic, drive, and passion for winning were contagious. He became beloved in Toronto and his postseason performances solidified his place in the team’s lore. His number 93 was retired in 2011. The Gilmour trade was one of the most transformative moves in Maple Leafs’ history. It gave the team a superstar who would dominate the NHL for years. It provided the team with leadership and a level of competitiveness that had been missing for far too long.

The Lasting Legacy of These Maple Leafs Trades

These three trades—acquiring Rick Vaive in 1980, Mats Sundin in 1994, and Doug Gilmour in 1992—are the cornerstones of Maple Leafs history. Each deal was more than just a player-for-player exchange; they were franchise-defining moves that brought in superstars who would become synonymous with the team.

Looking back on these trades, it’s easy to see how they shaped the franchise’s success, both in terms of on-ice performance and cultural identity. While the Maple Leafs have had their share of struggles until recent years, the legacy of these trades serves as a reminder of the pivotal moments in the team’s history that helped solidify its place among the NHL’s elite.

Related: Maple Leafs’ Five Most Regrettable Trades in History