In the heart of Toronto, hockey isn’t just a game, it’s a legacy carried by legends whose names resonate beyond the ice. For nearly a century, the Maple Leafs have been home to players whose talent and tenacity carved unforgettable chapters.
From the thunderous cheers in packed arenas to the quiet moments that define careers, these players shaped the franchise’s identity. Their influence runs deeper than records—they embodied the spirit of a city that lives and breathes hockey.
Each era introduced heroes whose impact transcended the scoreboard, leaving marks on the franchise’s legacy. Their stories intertwine with the city’s heartbeat, forming a lasting imprint on the team’s place within NHL history.
20. Syl Apps Jr.
Syl Apps Jr. (Source: Alchetron)
Carrying the torch from his legendary father, Syl Apps Jr. brought his own grit and skill to the Leafs during the 1960s and ’70s. A hardworking, reliable center, he embodied Toronto’s resilient spirit through challenging seasons. Though he never reached the heights of his father’s fame, his dedication and professionalism earned him respect on and off the ice.
19. Harry Watson
Harry Watson (Source: NHL Auctions)
Harry Watson stood out during hockey’s shift from amateur to professional eras, making his mark as an unstoppable forward for Toronto. Known for his speed, skill, and scoring instinct, he played a key role in securing the Leafs’ 1922 Stanley Cup. His elegant style and timely breaks laid the groundwork for the team’s offensive tradition in the decades to come.
18. Gordie Drillon
Gordie Drillon (Source: HockeyGods)
Gordie Drillon was one of the earliest forwards to transform the game with his accuracy and scoring touch. In the 1930s, he led the NHL in goals in 1938, helping Toronto establish itself as a powerhouse.
His mastery of offensive positioning and ability to read goaltenders made him a pioneer of strategic shooting. His legacy endures as an early architect of the Leafs’ attacking identity.
17. Doug Bentley
Doug Bentley (Source: Third String Goalie)
Doug Bentley was a scoring dynamo in the 1930s and ‘40s, dazzling fans with his speed and agility before the age of helmets and protective gear. As part of the famed “Pony Line,” his smooth hands and relentless attack made him one of Toronto’s earliest offensive stars. Though his career was interrupted by WWII service, his skill helped lay the foundation for the Leafs’ later success and remains a proud chapter.
16. Ian Turnbul
Ian Turnbul (Source: @oldhockeycards)
Ian Turnbull may not be the first name that comes to mind for casual fans, but his impact as a smooth-skating defenseman in the 1970s was significant. Known for his offensive skills from the blue line, he set a franchise record with 21 goals by a defenseman in one season (1976-77). His ability to quarterback the power play and contribute clutch points helped define the Leafs’ style during a transitional era.
15. Auston Matthews
Auston Matthews #34 of the Toronto Maple Leafs looks on during the third period against the Philadelphia Flyers at the Wells Fargo Center on March 14, 2024. (Source: Tim Nwachukwu/Getty Images)
Auston Matthews arrived in Toronto carrying the weight of a storied franchise—and he quickly became its new beacon. His lethal shot and hockey IQ redefined the Leafs’ offense, winning the Calder Trophy in 2017 and leading the league in goals multiple times.
Beyond numbers, he represents a new generation: calm under pressure, a fierce competitor, and a leader who blends skill with humility. His rapid ascent makes him one of the most electrifying talents in Leafs history.
14. King Clancy
Francis “King” Clancy (Source: NHL)
Francis “King” Clancy was a true hockey pioneer, known for his fiery competitiveness and versatility on the ice. Playing multiple positions, his leadership helped the Leafs win two Stanley Cups in the 1920s and 1930s.
Off the ice, he became a beloved ambassador of the sport, contributing as a coach, referee, and executive. His legacy extends beyond stats; He embodied the passion and spirit that built the Leafs’ foundation.
13. Wendel Clark
Leftwinger Wendel Clark of the Toronto Maple Leafs in 1991. (Source: Ken Levine /Allsport)
Wendel Clark was the raw, unapologetic heart of the Leafs in the late ’80s and early ’90s. His fiery leadership and physical style made him a fan favorite, while his knack for clutch goals solidified his legacy.
Known for his toughness and relentless drive, he wasn’t just a player; he was a symbol of the city’s fighting spirit during a time of transition. His #17 jersey remains one of the most beloved in franchise history.
12. George Armstrong
George Armstrong waves to the crowd beside Red Kelly and David Keon during a ceremony commemorating the 50th anniversary of the Leafs 64′ Stancley Cup in 2013. (Source: Abelimages/Getty Images)
George Armstrong was the embodiment of dedication and leadership, wearing the Maple Leafs sweater for 21 seasons. Nicknamed “Captain Crunch” for his physical style, he captained Toronto to four Stanley Cups in the 1960s, setting a tone of toughness combined with quiet determination.
Though not the flashiest scorer, his steady presence and relentless work ethic made him the team’s backbone, and he remains one of the longest-serving captains in NHL history.
11. Doug Gilmour
Doug Gilmour #93 watches the pregame ceremonies prior to the Hockey Hall of Fame Legends Classic Game at the Air Canada Centre on November 16, 2014. (Source: Bruce Bennett/Getty Images)
Doug Gilmour’s arrival in Toronto marked a revival. A tenacious centre with a penchant for clutch plays, he spearheaded the Leafs’ surprising playoff runs in the early 1990s.
His 127-point season in 1992–93 remains one of the best in franchise history. His leadership extended beyond stats: he was the heart and soul of a team hungry to rewrite its narrative. His gritty style and vision on the ice earned him a beloved spot in Leafs history and among fans.
10. Mats Sundin
Mats Sundin #13 skates in the Hockey Hall of Fame Legends Classic Game at the Air Canada Centre on November 16, 2014. (Source: Bruce Bennett/Getty Images)
Mats Sundin embodied consistency and class as Toronto’s first-ever European captain, a role he embraced from 1997 to 2008. His towering presence on ice and smooth, strategic play helped lift the franchise through a challenging era.
His 420 goals and nearly 987 points remain franchise records, a testament to his relentless scoring and playmaking ability. Beyond numbers, his leadership in the locker room and respect around the league set a high standard for future Maple Leafs, bridging eras and styles with grace.
9. Darryl Sittler
Darryl Sittler waves to fans during pre-game ceremonies before the game between the Toronto Maple Leafs and the Montreal Canadiens at the Bell Centre on January 08, 2009. (Source: Richard Wolowicz/Getty Images)
When it comes to Maple Leafs legends, Darryl Sittler’s name resonates as the ultimate scoring machine. Known for his blend of skill and grit, he exploded onto the scene in the 1970s, famously setting the NHL record with 10 points in a single game in 1976—a mark that still stands.
His leadership as captain was undeniable, steering Toronto through tumultuous seasons with a fierce competitive spirit. His offensive prowess earned him a place among the franchise’s all-time leaders, and his impact still echoes in the Leafs’ pursuit of glory.
8. Börje Salming
Borje Salming #21 skates during the Hockey Hall of Fame Legends Classic Game at the Air Canada Centre on November 16, 2014. (Source: Bruce Bennett/Getty Images)
A true pioneer, Börje Salming broke icebergs and barriers alike. The first European-trained player to make a major impact in the NHL, he arrived in 1973 to join the Maple Leafs and stayed for 16 seasons—a remarkable run crowned by franchise records in assists and longevity.
His physical bravery—famously returning to play after a 250-stitch facial injury—only deepened his legend. Hall of Fame-bound since 1996, his name graces the rafters and a Courage Award keeps his spirit alive.
7. Tim Horton
Tim Horton (Source: @CraigBaird)
In an era of physical hockey, Tim Horton stood out less for aggression and more for pure, iron-clad strength. A stay-at-home defenseman with a surgeon’s shot, he anchored the Leafs’ blue line over nearly two decades, playing a record 486 straight games and winning four Cups.
Bobby Hull once quipped that Horton’s strength made him respect the man rather than fear dirty hits. Off the ice, his legacy grew sweeter: co-founder of Canada’s iconic coffee chain, turning his name into a national institution.
6. Frank Mahovlich
Frank Mahovlich attends the ceremony honoring Andy Bathgate and Harry Howell prior to the game between the Toronto Maple Leafs and the New York Rangers on February 22, 2009. (Source: Bruce Bennett/Getty Images)
There was no player whose arrival demanded more attention than “The Big M.” Towering, elegant, and unpredictable, Frank Mahovlich’s game unraveled defenders with a galloping stride more reminiscent of a horse on the loam than a skater on ice.
From the mid-50s through the verge of the 70s, he carried the Leafs on his broad shoulders, leading the club in goals and points in virtually every season of his prime and anchoring four of their last Stanley Cups in the Original‑Six era.
5. Johnny Bower
Johnny Bower walks onto the ice before NHL action at the Air Canada Centre January 21, 2013. (Source: Abelimages/Getty Images)
Every dynasty needs a wall—Johnny Bower was Toronto’s. Dubbed “The China Wall,” he arrived as a late-career revelation, anchoring the net for a Maple Leafs dynasty in the 1960s with uncanny resilience and positioning that made breakaways feel futile.
While some guessed his age as much as his secretive past, his results were undeniable: four Stanley Cups, two Vezina Trophies, and a league-best career as one of history’s greatest goaltenders.
A former soldier turned farm‑league legend, he mastered the poke check before it was cool, battled blurred vision, and emerged in his 40s as a guardian between pipes. Even long after retirement, his legacy persisted—in coin, stamp, and statue alike.
4. Teeder (Ted) Kennedy
Teeder Kennedy (Source: NHL)
Ted “Teeder” Keenedy might have sounded like childhood mispronunciation, but his leadership was no mistake. Signing with Toronto at just 17, he quickly became the heart of a dynasty, lifting five Stanley Cups and claiming the Hart Trophy in 1955.
Known as a relentless forechecker and clutch playoff presence, he still holds the franchise record for points in Stanley Cup Finals. Conn Smythe even regarded him as “the greatest competitor in hockey,” a testament to his drive and consistency. Named captain at just 22 in 1948, he embodied the Maple Leafs’ resilient spirit through a golden era.
3. Charlie Conacher
Charlie Conacher (Source: @MapleLeafs)
A hulking figure at 6-foot-1 and nearly 200 pounds, Charlie Conacher earned the nickname “The Big Bomber” for a cannon-like shot that rattled nets long before the slap-shot era was even born. In the early 1930s, he formed the famed “Kid Line” alongside Joe Primeau and Busher Jackson—a combination that powered Toronto to the 1932 Stanley Cup and turned heads across the NHL.
Over five seasons from 1930 to 1936, he led the league in goals five times and in scoring twice. His legacy lives on in the Hall of Fame and in the memories of fans who still recall the earth-shaking slap of his shot.
2. Syl Apps
Syl Apps (Source: NHL)
Before Syl Apps skated onto NHL ice, he soared over vaulting bars. A Commonwealth gold medalist and Olympic pole vaulter in 1936, his rare mix of athleticism and dignity caught Conn Smythe’s eye.
With Toronto, he was an immediate force: Calder winner, Lady Byng recipient, and the anchor of three Stanley Cups. He captained the Leafs through the war years with steely calm, recording over 400 points while amassing just 56 penalty minutes. A national hero both on and off the ice, he later served in politics, embodying the kind of leadership that transcended sport.
1. Dave Keon
Dave Keon (Source: NHL)
Grace on skates, precision without noise—Dave Keon wasn’t just a Maple Leaf, he was the pulse of an era. Standing 5’9″, he built a career on speed, balance, and defensive brilliance. After debuting in 1960, he won the Calder Trophy and never looked back.
Four Stanley Cups followed, and in 1967 he silenced Jean Béliveau en route to the Conn Smythe Trophy—still the only Leaf ever to win it. Over 1,000 games in blue and white, he became a master of the penalty kill and a poster child for fair play, collecting two Lady Byngs. His quiet dominance didn’t demand attention—it earned respect.
