The Toronto Maple Leafs have a rich history filled with talented players, and their wingers are no exception. Narrowing down the five best of all time is a difficult task, sparking debate among fans. Here’s a look at five of the most exceptional wingers to have graced the ice for the Leafs:

1. George Armstrong: Universally known as "Chief" due to his mother's heritage, Armstrong spent his entire 21-season NHL career with the Toronto Maple Leafs. He is one of only two right wingers to play over 1,000 regular-season games for Toronto. Armstrong holds the title of highest-scoring right-winger in Maple Leafs history. Although critics initially doubted his NHL prospects, citing his skating and shooting, his heart and leadership led him to become an all-time great Maple Leafs captain. Armstrong recorded 713 points (296 goals, 417 assists) in 1,187 regular-season games. He also contributed to four Stanley Cup victories and was a seven-time NHL All-Star. A statue of Armstrong was erected on Legends Row in 2015.

2. Frank Mahovlich: "The Big M" is considered one of the best left wingers in Maple Leafs history. Mahovlich won the Calder Trophy as rookie of the year in 1957-58 after a strong 20-goal season. During his 12 seasons with the Maple Leafs, he helped them win four Stanley Cup championships in the 1960s. Mahovlich holds the franchise record for left-wingers with 597 regular-season points (296 goals, 301 assists) in 720 games. He was inducted into the Hockey Hall of Fame in 1981.

3. Lanny McDonald: McDonald was drafted by the Maple Leafs in 1973. Although it took him a few seasons to develop, he became a star under coaches Red Kelly and Roger Nielson. Nielson paired McDonald with Darryl Sittler, and McDonald became a fan favorite. In his seven seasons with the team, McDonald accumulated 459 points (219 goals, 240 assists). He ranks fourth in all-time points for Maple Leafs right-wingers.

4. Mitch Marner: Marner is a modern-era star who has made a significant impact on the Maple Leafs. Drafted fourth overall in 2015, Marner quickly became an integral part of the team's offense. In nine seasons with the team, he played 657 games, scoring 221 goals and 750 assists for a total of 741 points. Despite his departure from the team earlier in the summer, Marner's offensive contributions place him among the best wingers in franchise history.

5. William Nylander: Nylander is currently one of the premier players on the Maple Leafs roster. Known for his offensive awareness and accurate shot, Nylander has consistently performed at a high level. In the 2024-25 season, he scored a career-high 45 goals, leading all Leaf skaters. Nylander has recorded three consecutive 40-goal seasons and is among the top-rated right wingers in the NHL.

These five wingers represent a blend of different eras, each leaving an indelible mark on the Toronto Maple Leafs. While other names like Wendel Clark, Bob Pulford and even Phil Kessel could be considered, these five have consistently been recognized for their outstanding contributions to the team.