Top 15 Toronto Maple Leafs Who Had To Leave To Chase A Stanley Cup

For the Toronto Maple Leafs and the franchise's fan-base, it's been a long and painful drought since the club won its' last Stanley Cup championship (1967). Since that time, the Original Six franchise has proceeded to draft and acquire a number of notable all-star and Hockey Hall Of Fame caliber skaters. However, as noted above, that flashy list of players that have donned the iconic Leafs sweater in recent memory never hoisted Lord Stanley with Toronto.

Still, that's not to say that those notable names didn't win a Stanley Cup before arriving in Toronto or won a ring after departing from the Maple Leafs. Nothing could be more agitating to all Toronto fans than watching a handful of former top Maple Leafs players of all-time go on and win a cup with another NHL club, nonetheless a rival too.

Then, there's another unique list of former and noteworthy Leafs' players, who from Toronto's sake, luckily didn't end up winning a Stanley Cup championship after leaving one of the NHL's most popular hockey cities.

TheSportster lists the Top Five Toronto Maple Leafs Who Won A Stanley Cup With A Different Team, & 10 Who Tried But Failed.

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17 Won: Tomas Kaberle

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For almost a decade, the Toronto Maple Leafs’ blue line entailed one of the best offensive talented defenseman any NHL club could ask for. That skater for the Maple Leafs was, Tomas Kaberle. The Czech Republic native was surprisingly a late-round draft-pick (eighth-round) in 1996, but as soon as Kaberle hit the ice in 1999 with the Big Club – his impact was known from the get-go.

The six-foot-one and 216lbs D’man played a major role with the club during a number of Stanley Cup Playoff runs and appearances, especially in the early 2000’s. However, Kaberle and Toronto eventually had to go their separate ways…and the Czech ended up winning a Stanley Cup with one of the Leafs’ top rivals, which happened to be the Boston Bruins in 2011.

16 Tried: Sergei Berezin

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Yes, former Toronto Maple Leafs playmaker Sergei Berezin had what could be labeled as a short NHL career, but the Russian forward is remembered as one of the top skaters to don a Leafs’ sweater. Berezin spent five seasons with Toronto, while finding the back of the net at least 20 times or more in four of those campaigns.

After the 2001 season, the five-foot-ten forward left the Maple Leafs and signed a contract with the (then) Phoenix Coyotes. At the time, the Yotes were Stanley Cup contenders, yet Berezin was later traded that same season to the Montreal Canadiens. The Habs would run into a hot Carolina Hurricanes club during the 2002 playoffs and were eliminated in six games during the Eastern Conference Semi Finals.

15 Won: Dave Andreychuk

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Former Tampa Bay Lightning forward and team captain, Dave Andreychuk, played over two decades in the NHL and while dressing for six different clubs. The Hamilton, Ontario native also played in Toronto with the Maple Leafs for parts of four seasons from 1993-1996. Andreychuk earned 214 career regular season points with the Blue and White, and also recorded 34 career points in three separate Stanley Cup Playoff appearances with Toronto.

While Andreychuk spent parts of the next six seasons playing for the New Jersey Devils, Colorado Avalanche, Buffalo Sabres and Boston Bruins, it was with the Lightning in 2004 when the six-foot-four skater finally hoisted Lord Stanley for the first time. Keep in mind, the Leafs and Andreychuk reached the (then) NHL Conference Finals back-to-back seasons (1993 & 1994), but lost each time.

14 Tried: Darcy Tucker

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Former Montreal Canadiens’ draft-pick (1993), Darcy Tucker, played parts of seven seasons with the Toronto Maple Leafs from 2000-2008, and became a fan-favorite from the get-go. There were heartbreaking losses in the Stanley Cup Playoffs during that duration mentioned above for both Tucker and the Leafs, which also included losing in the Conference Finals to the Carolina Hurricanes in 2002.

After the 2008 season, Tucker left the Leafs and signed a contract with the Western Conference’s Colorado Avalanche. There was potential in Colorado for the team to get back to its Stanley Cup caliber play, however the Avs were eliminated in the second-round of the 2010 playoffs to the San Jose Sharks and in six games. Tucker would retire that same offseason, and goes down as one of the top players to don a Leafs’ sweater.

13 Won: Vincent Damphousse

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In 1986, the Toronto Maple Leafs selected forward Vincent Damphousse with the sixth-overall-selection at the NHL Entry Draft. After spending five seasons donning the Blue and White’s classic hockey sweater, the Montreal, Quebec native had totaled 329 career points. Yet, Damphousse was eventually acquired by the Leafs’ biggest rival, the Montreal Canadiens in 1992.

Damphousse prospered with a stacked Habs squad during the 1992-93 campaign. He recorded career highs of 97 points during the regular season and 23 points during the Canadiens’ Stanley Cup Finals run that same season. And, the Toronto faithful witnessed another all-time great hoist Lord Stanley after leaving Toronto for another club. While that was the only Stanley Cup ring he received as an NHL player, it still stings the Leafs to date.

12 Tried: Dmitri Yushkevich

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Russian defenseman Dmitri Yushkevich spent five seasons playing for the Toronto Maple Leafs, and was a key member for a number of Leafs’ teams that clinched a string of Stanley Cup Playoff appearances in the early 2000s. Yet, the stay-at-home defenseman ended up leaving those same successful Toronto teams, and was acquired by the Philadelphia Flyers towards the latter half of the 2002-03 regular season.

The Flyers were in a position to make a legitimate Stanley Cup run, but ran into a hot Ottawa Senators club during the 2003 Eastern Conference Semi Finals. The Flyers lost in six games, and Yushkevich’s dream of hoisting Lord Stanley came to an end that spring. The five-foot-eleven skater retired from the NHL that same offseason and continued to play Professional Hockey overseas in Russia.

11 Won: Phil Kessel

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Since NHL forward Phil Kessel entered the league in 2006-07, there’s always been some sort of drama cloud that hovers over the six-foot winger. Kessel, now age 29, spent six seasons donning (2009-2015) that of a Toronto Maple Leafs jersey, but the Toronto media and new front office management eventually drove the former first-round draft-pick (Boston Bruins – 2006) out of town.

The sniper found the back of the net 181 times and totaled 394 career regular season points in Toronto during the duration mentioned above. And, just when things couldn’t have stung Leafs fans anymore – Kessel was not only traded to the Pittsburgh Penguins to join two of the best players in the World (Sidney Crosby and Evgeni Malkin), but Kessel won a Stanley Cup with the Pens in his first season with the club. Fans across the NHL still argue that Kessel should’ve won the Conn Smythe Trophy over Crosby, too.

10 Won: Lanny McDonald

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Hockey Hall Of Famer and Toronto Maple Leafs legend Lanny McDonald ended up winning one Stanley Cup during his 15-year NHL career, but it was not with his beloved Leafs. After spending parts of six seasons with Toronto, the Alberta native was traded to the Colorado Rockies during the middle of the 1979-80 regular season; and by the unpopular (then) Leafs’ General Manager, Punch Imlach.

McDonald was eventually acquired by the Calgary Flames during the early stages of the 1981-82 regular season, and the former first-round draft-pick (1973) won a Stanley Cup with the Flames during his final NHL season (1989). McDonald help lead Calgary past a powerhouse club in the Montreal Canadiens during the Finals, as the Flames won the series in a surprising six games.



7 Tried: Ian Turnbull

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In 1977, Toronto Maple Leafs defenseman Ian Turnbull set an NHL record (that still stands to date), as Turnbull scored five goals in one game and on just five shots against the Detroit Red Wings. The six-foot and 200-pound skater goes down as one of the best Maple Leaf players of all-time, but unfortunately also joins a list of Greats that failed to bring a Stanley Cup back home to Toronto.

After spending parts of nine seasons in Toronto, Turnbull was acquired by the Los Angeles Kings during the early stages of the 1981-82 campaign. There was hope that the Maple Leafs’ former stud D’man would have a shot at winning a Stanley Cup in City of Angels, but the Kings fell just shy – losing in the (then) Division Finals to the likes of the Vancouver Canucks in five games.

6 Tried: Todd Gill

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From 1984 until the end of the 1996 NHL season, defenseman Todd Gill donned that of a blue and white Toronto Maple Leafs sweater. Gill goes down as one of the top skaters in the franchise’s history, yet the former second-round draft-pick (1984) never hoisted Lord Stanley with the Original Six Franchise in the Leafs.

After the 1996 campaign, Gill left the Leafs and went on to play for six different Western Conference teams; all whom were Stanley Cup Playoff contenders (San Jose Sharks, St. Louis Blues, Detroit Red Wings, Colorado Avalanche and (then) Phoenix Coyotes. At the time, the Red Wings were a powerhouse and Cup favorite each season (1999-2001). Still, timing is everything is sports, and it just so happened those were three years the Wings were unable to reach the Stanley Cup Finals (Had won three Cups from 1997-2002).

5 Tried: Rick Vaive

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The Toronto Maple Leafs clinched a handful of Stanley Cup Playoff appearances throughout the 1980s, and one top player from those Toronot teams was forward Rick Vaive. The Ottawa, Ontario native recorded 537 career points as a Maple Leaf, but Toronto came up short in each of its’ playoff appearances during that decade.

After eight seasons in Toronto, Vaive left the Leafs and joined a strong Chicago Blackhawks team for the 1987-1988 season. But, the Hawks were eliminated by the St. Louis Blues that postseason and the winger found himself eventually trying to win a Stanley Cup with a different organization yet again. Vaive spent his final three NHL seasons with the Buffalo Sabres (making the playoffs in each), but the Sabres lost in the (then) Division Semi Finals during all three appearances.

4 Tried: Doug Gilmour

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Yes, Doug Gilmore did win a Stanley Cup prior to joining the Maple Leafs in 1991-92 with the 1989 Calgary Flames. But, after consecutive losses in the NHL’s Conference Finals in the early-to-mid 90s, Gilmour left Toronto for a Cup contending New Jersey Devils team in 1997.

The ideal wedding between the Devils and Gilmour lasted only one season after the trade, and Jersey’s Team finished as one of the league’s best clubs in 1998. It appeared Gilmour was on his way to winning another Stanley Cup championship and with a team other than the Leafs; but the Devils were upset during the Eastern Conference’s first-round of the playoffs and by the likes of the eighth-seeded Ottawa Senators. Gilmour eventually left the Devils for the Chicago Blackhawks the following season and was unable to hoist Lord Stanley post-Toronto playing days.

3 Tried: Wendel Clark

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Former NHL forward Wendel Clark laced up the skates with the Toronto Maple Leafs on three separate occasions throughout his 15-year NHL career. While Wendel dressed for five other clubs during that time frame (1985-2000), the former first-overall-pick (1985) never won a Stanley Cup championship.

Wendel was reacquired by the Leafs at the 1996 NHL Trade Deadline, after being traded to the Quebec Nordiques (Mats Sundin trade) in 1995, but still came up empty handed with Toronto for parts of the next three seasons. And, Wendel found himself acquired by the defending Stanley Cup champion Detroit Red Wings in 1999 – but Wendel and the Wings lost in the second-round of the Stanley Cup Playoffs to the Colorado Avalanche. Wendel finished his career in 2000 with the Maple Leafs, who were then bested by the New Jersey Devils in six games during the second-round of the playoffs.

2 Tried: Curtis Joseph

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Canadian born netminder Curtis Joseph made his presence known between the pipes for 20 years in the NHL, which also included playing for five different teams. Still, “Cujo,” is more than likely remembered most as a Toronto Maple Leaf. Joseph helped guide the Leafs to the Stanley Cup Playoffs for four consecutive years (1999-2002), and had established himself as one of the league’s best goaltenders at the time.

However, after failing to actually reach the Stanley Cup Finals in each of those four memorable seasons, Joseph decided to leave Toronto. During the 2002 offseason, the Leafs’ beloved Cujo addressed the Toronto media and emotionally announced that he would be leaving Toronto to join a team that had a better opportunity at a winning a Stanley Cup. That team happened to be the (then) defending Stanley Cup champion, Detroit Red Wings. Yet, Joseph only lasted two seasons in Hockeytown, and came up short on getting his Stanley Cup ring.

1 Tried: Mats Sundin

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Swedish native Mats Sundin could potentially go down in history as the Toronto Maple Leafs most popular skater in retrospect to Leafs fans. Sundin was acquired by Toronto during the 1994 offseason and the club (most) notably traded away fan-favorite, Wendal Clark, to the (then) Quebec Nordiques as a part of the deal.

Sundin progressed as not only an all-star caliber NHL player with Toronto, but a Hockey Hall Of Famer. To date, Sundin is the club’s all-time leading scorer with 987 points. However, Sundin like other past players from the mid-1990s to early 2000s, including Curtis Joseph, never made it past the Eastern Conference Finals with Toronto. The former first-overall-pick (1989) chose to leave the Maple Leafs as an unrestricted-free-agent during the 2008 offseason, and in favor of a Cup contending Vancouver Canucks squad. However, the Canucks were upset in the second-round of the playoffs that season (2009) by the Chicago Blackhawks. Sundin then retired after the second-round playoff exit.

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