On May 2nd of this year, it will mark the 50th anniversary of when the Toronto Maple Leafs last won a Stanley Cup in 1967. In the last fifty years, the team has had many ups and downs. While they might not have won another Stanley Cup, they have come pretty close on multiple occasions. They wouldn’t have got as close to winning Lord Stanley if it wasn’t for some of the amazing players who have donned a Maple Leafs uniform throughout the years. They might not have achieved the ultimate goal, but they did pretty much everything else.
As many good seasons that the Leafs have had in the past fifty years, they may have even more poor ones. The 1980s was not a particularly strong decade for the team as they found themselves near the bottom of the standings more often than not. The last ten years have also not been so kind to the Leafs, as they have only made the playoffs once since 2005. While there were some good players that suited up for Toronto during these struggling years, there were definitely some players who didn’t even belong in the NHL to being with.
Here are the 15 best and the 15 worst Toronto Maple Leafs since their last Stanley Cup win in 1967.
41 Best: Tiger Williams
Dave "Tiger" Williams was one of the most charismatic players to ever play the game. He was best known for all his time spent in the penalty box. By the time his career was finished in 1988, he was the NHL's all-time leader with 3966 penalty minutes. Williams got his first taste of the penalty box in the NHL while as a member of the Maple Leafs. He played his rookie season with the Leafs in 1974-75 and stayed with the team until the 1979-80 season.
While it wasn't a super long stay in Toronto, Williams still made a long lasting impression with the fans in Toronto. While the fans loved seeing him dish out hits to opposing players, they also love to see him score. Williams may have been a tough guy, but he also had a decent scoring ability. While he scored double-digit goals in each of his seasons with the Leafs, he scored more than 20 goals on two different occasions.
40 29.Worst: Mike Craig
Mike Craig was a prolific scorer in junior while playing for the OHL’s Oshawa Generals. In his final season with the team in 1989-90, he scored 36 goals in just 43 games played. The Minnesota North Stars thought they might be getting the steal of the draft when Craig fell to them with 28th overall selection in the 1989 NHL Draft. Unfortunately for Craig and the Stars, he failed to live up to the lofty expectations. He played for four seasons with the franchise, never scoring more than 15 goals in a season.
The Maple Leafs still believed that Craig could still live up to the potential he once showed, so they signed him to a sizeable four-year contract. Craig had also stated that he had more to give and that he was being held back in his time with the Stars. He ended up lasting just three years with Toronto where his numbers regressed every year. While he had a couple of 15 goal seasons with the North Stars, he barely averaged 15 points a season while playing in Toronto.
39 Best: Ron Ellis
Ron Ellis (Pictured Waving) played 16 NHL seasons during his career, all as a member of the Toronto Maple Leafs. Although he got his start in the league, before the league expansion in 1964, his best years career took place during the 1970s. Ellis was known as one of the best two-way players in the game. When he was defending, he always made sure he did it in a clean way. This play style got him respect from players and coaches throughout the league.
While Ellis was great at keeping goals out of his own team's net, he was more than capable of putting pucks in the opposing team's net. He had nine straight season's where he scored at least twenty goals. His best offensive season of his career came in 1974-75 when he scored 32 goals and had a career-high 61 points.
37 Worst: Colton Orr
Throughout his entire hockey career, Colton Orr was nothing more than an enforcer. Even during his time in junior, he racked up the penalty minutes while never scoring more than nine points in a season. When Orr entered the NHL in 2005, the role of the tough guy was still something every team in the NHL had on their rosters. After a cup of tea with the Boston Bruins, Orr joined the New York Rangers in 2005. He would play four seasons with the Rangers where he gained the reputation of being one of the toughest guys in the league.
In 2009, the Maple Leafs made Orr one of the highest paid enforcers in the league when they signed him to a four-year, $4 million contract. His first season with the Leafs went as good as it probably could for a guy in his role. He recorded a career-high six points while finishing second in the league with 239 penalty minutes. After that season it went downhill for Orr and his time in Toronto. He failed to earn a full-time roster spot with the Leafs, and when he was in the lineup he was not at all effective. The role of the enforcer was dying out in the NHL, as you needed scoring on all four of your lines if you wanted to win. Orr had zero offensive upside, his zero points in 54 games in 2013-14 is evident of that.
36 Best: Phil Kessel
Phill Kessel's time in Toronto didn't go without some controversy. That is to be expected considering how much they gave up to acquire him. In 2009 the Leafs got Kesse from the Boston Bruins in exchange for two first round and one second round draft picks. One of those draft picks end up being a second overall pick, which Boston used to select the very talented Tyler Seguin.
With all the pressure on Kessel, he performed fantastically for the Leafs. In each of his six seasons with Toronto, he led the team in scoring. He also scored more than 30 goals in four seasons, including a career-high 37 goals during the 2013-14 season. While it's true that the Leafs only made the playoffs once during Kessel's tenure, it's safe to say the team would have been way worse without him.
34 Worst: Aki Berg
Aki Berg was a highly touted defenseman while playing junior hockey in his home country of Finland. Scouts loved his size as well as his big shot from the point. The Los Angeles Kings loved him too, and they took him with the third overall pick of the 1995 draft. He would last just four seasons with the Kings, where his play was only good enough to be a bottom pairing defenseman.
The Leafs would acquire Berg in a 2001 trade with the Kings. They were hoping they could get more out of the player who once was described as being a combination of Scott Stevens and Paul Coffey. The Leafs were never able to get anything more out of Berg in his four-plus seasons with the team. While Berg was not absolutely terrible, the fact that he was so mediocre after being so hyped up entering the league, earns him a spot on this list.
33 Best: Dave Andreychuk
Dave Andreychuk was one the best goal scorers to ever play the game, finishing his NHL career with an impressive 640 goals. He scored a good chunk of his goals as a Maple Leaf. While his tenure in Toronto was fairly brief, lasting just parts of four seasons, he made a big impact in his short time there. After he was traded to Toronto from Buffalo in 1993, he immediately made a big bang with the team. In just 31 games for the Leafs that season, he scored an incredible 25 goals. He also added another 19 points in the playoffs, helping the team reach the Conference finals.
Andreychuk's first full season with the Maple Leafs in 1993-94 was by far his best in Toronto. He led the team with 53 goals and tied a career high with 99 points. Although he remained one of Toronto's top point producers for the next couple of seasons, the team was struggling so they shipped him off to New Jersey in 1996.
32 Worst: Staffan Kronwall
Staffan Kronwall is the younger brother of long-time Detroit Red Wing's defenseman Niklas Kronwall. While Niklas has gone on to have a tremendous NHL career, Staffan has not been as fortunate. The younger Kronwall was a late round draft choice of the Maple Leafs back in 2002.
Kronwall spent four seasons with the Maple Leaf's organization, where he found himself mostly in the AHL. His performance in the AHL wasn't groundbreaking, but he showed a little bit of offensive flair while still being an opposing defenseman. His decent play in the minors allowed him to get into a 52 NHL games during his time with the Leafs. Kronwall contributed practically zero offense, just one assist, and played soft on defense. He was a big man at 6'5", 225 lbs, but he never used his size to his advantage. He ended up being nothing more than a liability with the Leafs.
31 Best: Curtis Joseph
Curtis Joeseph wasn't supposed to have much of a hockey career after not being drafted. However, he went on to have an amazing NHL career that spanned 19 seasons. Joesph first established himself a number one goalie in the NHL during his time with the St. Louis Blues in the early 1990s. When he was traded to the Edmonton Oilers in 1995, Joseph proved that he was an elite NHL goaltender.
In 1998, the Maple Leafs signed Joseph and he took his game to a whole other level. He recorded at least thirty wins in his first three seasons with Leafs and he was a runner-up for the Vezina Trophy in 1999 and 2000. What made Joseph such a great goalie was his ability to step up his game in the playoffs. Without "CuJo" in goal, Toronto would not have had the long playoffs runs that they had in the early 2000s.
29 21.Worst: Ryan Hollweg
A year after being drafted in the eigth round by the Rangers, Ryan Hollweg's offensive game was showing signs of improvement. In 2001-02, he had the most productive season of his career scoring 30 goals and 70 points. However, once Hollweg turned pro, his offensive game went out the window. Instead, he found a role on the Rangers as an enforcer.
After playing two full seasons in New York, Hollweg was traded to a terrible Leafs team. It was hard for the team to get any worse but with the acquisition of Hollweg they just that. He would play just 25 games with the team where he provided almost nothing. To make matters worse, Hollweg gave the team a bad reputation after he was twice suspended for dirty plays.
28 Best: Rick Vaive
Growing up, Rick Vaive's dream was to one day play for the Maple Leafs and win the Stanley Cup. While he never got a chance to lift Lord Stanley over his head, he did get a chance to play for Toronto and he made sure to make the most of his opportunity. After playing his first NHL season with the Vancouver Canucks, the power forward was traded to the Leafs in 1980.
After scoring 33 goals in his first season with the Leafs, Vaive would become the first ever Maple Leaf to score 50 goals in a season when he notched 54 goals in 1981-82. He would go on to score at least 50 goals in three consecutive seasons. In 1981 he was named the team captain, a position he held until he was traded the Chicago Blackhawks in 1987.
26 Worst: Andrew Raycroft
After playing in a handful of games in the NHL, Andrew Raycroft came out ready to play for his official rookie season in 2003-04. He posted some absolutely stellar numbers for the Boston Bruins, which included a 2.05 GAA, and a sparkling .926 save percentage. Raycroft was an easy decision to be named the NHL's rookie of the year. However, the following season, he struggled mightily with the Bruins, to the point where he actually found himself third on the depth chart.
In 2006, the Maple Leafs were in the market for a starting goalie, so they acquired Raycroft from Boston for future elite NHL goaltender Tuukka Rask. The Leafs were hoping that Raycroft would able to regain his rookie form. Although he would set a Maple Leafs record with 37 wins in his first season with Toronto, that stat was a bit misleading. Raycroft actually struggled, finishing 49th in goals against average and 56th in save percentage. Raycroft lasted just one more season with the Leafs before he was bought out, as his numbers were even worse than the year before.
25 Best: Lanny McDonald
The image that first comes to mind when most hockey fans think of Lanny Mcdonald, is the image of him with his trademark mustache lifting up the Stanley Cup in 1989 with Calgary Flames. However, McDonald arguably had the best years of his career as a member of the Maple Leafs. Toronto originally drafted McDonald with the 4th overall selection in the 1974 Amateur Draft.
Although Lanny got off to a bit of a slow start in first two seasons, his third season in the league was a breakout year for him. He finished second on the team with a career-high 93 points. He would go on to score at least forty goals and eighty points for his last three seasons as a Leaf. The highlight of McDonald's tenure in Toronto occurred in the 1978 playoffs when he scored the game-winning overtime goal to help the Leafs defeat the Islanders on their way to the Stanley Cup semi-finals.
23 Worst: Mike Komisarek
Mike Komisarek made a name for himself in the NHL as a member of the Montreal Canadiens, where he was known as a rugged stay-at-home defenseman. He became a fan favorite in Montreal because he wasn't afraid of blocking shots or sticking up for his teammates. He was so popular in Montreal that fans actually voted him into the 2009 NHL All-Star game.
In the 2010 offseason, the Maple Leafs were looking to stabilize their blueline and they thought Mike Komisarek was the perfect man for the job. They signed him to a hefty five-year contract worth $4.5 million per season. His run in Toronto ended up being disastrous for the most part. In his first season in Toronto, he missed half the season with a shoulder injury. When he was in the lineup, he wasn't the steady force the team had hoped, as he had a minus-nine rating. Komisarek's play never got any better with the Leafs, and in 2013 the team bought out the rest of his contract.
22 Best: Felix Potvin
Felix Potvin had success everywhere he played, at every level. He was one top the goalies in junior while playing for the QMJHL's Chicoutimi Sagueneens, winning goaltender of the year in 1991. In his very first pro season with the Maple Leafs AHL farm team, he won the goalie of the year and was also named the rookie of the year. When he joined the Maple Leafs full-time in the 1992-93 season, he took no time get acclimated the NHL game. Not only did he lead all rookie in wins with 25, he absolutely stood on his head in the playoffs.
While Potvin and Toronto came up short in Conference finals, it was looking like they had found their goalie of the future. Potvin's second season with the Leafs was just as good as his first. He won a career-high 34 games while once again helping Toronto with a deep playoff run. Potvin would play parts of eight seasons with the Leafs, and by the end of his tenure in 1999, his stats ranked up there with some of the greatest goalies in team history.
20 Worst: Rick St. Croix
Rick St.Croix was originally drafted by the Philadelphia Flyers in the 1975 NHL Draft. He would spend years plying his craft in the minors before finally becoming a full-time NHL goalie during the 1980-81 season. After couple decent seasons as a backup with the Flyers, St.Croix thought he was in line to become the new number one goalie in Philly. The starting job ended up going to Pelle Lindbergh instead. St.Croix publicly displayed his displeasure about not getting that starting job, and one year later the team traded the angry goaltender to Toronto.
St.Croix never got the starting job in Toronto either, mostly because in the games he did get into, he was terrible. He played in 48 games during his three seasons with the Leafs, posting a dismal 11-28-2 record with an ugly 4.67 GAA, and a .858 save percentage. After his time in Toronto was done in 1985, so was his career.
19 Best: Tomas Kaberle
Tomas Kaberle was originally an eighth round draft choice of Toronto back in 1996. The fact that he was such late round draft pick, meant it was going to take a lot of hard work for Kaberle to one day make the NHL. Not only did he make it the NHL at a very young age, but he went on to become of greatest defenseman in Maple Leafs history.
With each passing season, Kaberle seemed to get better and better. After just a few years in the league not only was Kaberle one of the best offensive defensemen on Toronto, he was one of the best in the entire league. While Kaberle had the unfortunate pleasure of playing on some poor Maple Leaf teams, he was always a bright spot. His best offensive year of his career came in 2005-06 when he finished 4th in the league in scoring by a defenseman with a career-high 67 points.
17 14.Worst: Frazer McLaren
Frazer McLaren is a big man at 6'5", 230 lbs. The San Jose Sharks were attracted by that size as well as his grit and took him in the seventh round of the 2007 draft. McLaren would play parts of five seasons with Shark organization where he found himself mostly playing in the minors. Although he had a decent run with San Jose in 2009-10 when he recorded 6 points in 17 games, he was mostly ineffective whenever he got inserted into the Sharks lineup.
In 2013, the Leafs were looking to add some toughness to their lineup. So when Frazer McLaren was put on waivers by the Sharks, they scooped him up. McLaren would play 35 games for the Leafs that season where he played well enough to earn a two-year contract extension. It ended up being a terrible decision by the Leafs, as MacLaren only played 27 more games for the team, failing to register a single point. Toronto had a bunch of useless plugs in their lineup during the 2013-14 season, and Frazer McLaren might have been the most useless of all.
16 Best: Dave Keon
Some people will argue that Dave Keon is the greatest Toronto Maple Leaf of all-time, and they wouldn't be wrong. He entered the league during the 1960-61 season, and made an immediate impact by winning the rookie of the year. He would go on to have six straight seasons of twenty goals or more. He also played a role in helping the Maple Leafs win their very last Stanley Cup in 1967. It is because of the fact that Keon played half of his career before 1967, that he isn't higher on this list.
The second half of Keon's hockey career was arguably better than the first half. He may not have won another Stanley Cup, but he did have some of the most productive years of his career. The best offensive season of his career came in 1972-73, when he finished second on the team with a career-high 76 points. By the time he played his last game as a Maple Leaf in 1975, he was the franchise's all-time leading scorer.
14 Worst: Philippe Dupuis
Phillippe Dupuis was a prolific scorer in junior, scoring 108 points during his final season with the Moncton Wildcats of the QMJHL. Unfortunately for him, his offensive skill never translated to the NHL. After putting up decent numbers at the AHL level, Dupuis finally got a full-time roster spot with the Colorado Avalanche during the 2010-11 season. He recorded a respectable six goals and 17 points.
The Maple Leafs were looking to add some depth to their forwards, so they signed Dupuis to a contract in 2011. They were hoping Dupuis could build on his first full NHL season, but he actually regressed. The Leafs were a terrible team in 2011-12, and Dupuis did absolutely nothing to help them. He suited up for thirty games for the team and produced a grand total of zero points. While fellow Leaf Jay Rosehill also produced zero points in 31 games, at least he had a role as an enforcer. Dupuis was just a complete waste of ice time.
13 Best: Wendel Clark
There might not be a more popular player in the history of the Toronto Maple Leafs than Wendel Clark. The Leafs took Clark with the very first pick of the 1985 NHL draft. He was actually a defenseman in junior but the Leafs thought he would make an even better forward. The position change turned out to be a great move as Clark became a dominant power forward. As good as he was at laying out hits, he might have been an even better goal scorer.
In 1992-93, the Leafs made a run all the way to the Conference finals, and Clark played a huge role in that. He finished second on the team with 20 playoff points. The 1993-94 season would be a career year for Clark as he scored a career-high 46 goals in just 64 games. Wendel Clark had a terrific NHL career but it could have been so much better had numerous injuries not derailed his production.
12 Worst: Jim Rutherford
Jim Rutherford may be best known today as a two-time Stanley Cup winning general manager with Carolina and Pittsburgh, but he actually first had a lengthy NHL career as a goaltender. Rutherford played 14 NHL seasons, with ten of them being as a member of the Detroit Red Wings. While his numbers in Detroit were nothing spectacular, he was at least consistently average.
During the 1980-81 season, Rutherford had seen himself get pushed farther and farther down the Red Wings depth chart. With the team no longer needing him, he was shipped off to the Maple Leafs. His stay in Toronto lasted just 18 games where he posted some of the worst numbers of his career. The one stat that particularly stood out in a bad way was his ugly 5.12 GAA.
11 Best: Doug Gilmour
By the time Doug Gilmour joined the Maple Leafs midway through the 1991-92 season, he was already a well established NHL player. He began his career with the St.Louis Blues where he topped the 100 point mark during the 1986-87 season. In 1988 he joined the Calgary Flames, where he helped the team capture the Stanley Cup in 1989.
Despite all the previous success in his career, Gilmour took his game to another level in Toronto. While remaining a solid defensive forward, Gilmour set a Maple Leafs record by scoring 127 points during the 1992-93 season. He was even better in the playoffs as he led the league with 25 assists while helping the team reach within one game of the Stanley Cup finals. Gilmour followed up that season with another 100 point plus campaign. He would go on to have another three great seasons in Toronto before he was traded to New Jersey in 1997.
9 Worst: David Clarkson
David Clarkson first entered the NHL as undrafted free agent with the New Jersey Devils in 2006. In his first few seasons in the league, he proved to be one of the most agonizing players to play against, while also showing a bit of a goal scoring touch. The 2011-12 season was extra special for Clarkson when it came to goal scoring, as he scored a career-high thirty goals.
After scoring 12 goals in 48 games the following season, Clarkson was ready to test free agency. The Maple Leafs were desperate for offense, so they signed him to a massive seven-year contract worth $36.75 million. That is a great deal of money for a player who only really had one outstanding season. As most people expected, the signing of Clarkson turned out to be a complete disaster. He scored just a combined 15 goals over two seasons for the Leafs. Toronto was able to pull off a minor miracle by trading Clarkson to Columbus in 2015.
8 Best: Borje Salming
If it wasn't for a bit of luck and being at the right place at the right time, Borje Salming would have never even been a member of the Maple Leafs. In 1973, Toronto went to Sweden to scout a different player they liked. That is when the scouts got a chance to see Salming play, and they were too impressed by him not to sign him. Salming would go on to not only to be one of the first Swedish superstars in the NHL, but he would become the greatest defenseman in Maple Leafs history.
While there was no doubt that Salming loved contributing offensively, having four seasons where he recorded seventy-plus points, he was actually such a well-rounded defenseman. He took pride being a human shield in front of the Leafs net. He was also relied on to play huge minutes for the team, even when he was nearing the age of forty. By the time he left the organization in 1989, he ranked first in all-time assists (622), and ranked third in team history with 1099 games played.
6 Worst: Carter Ashton
There was a time where Carter Ashton was a highly touted prospect. The former 2009 first round draft pick of the Tampa Bay Lighting even had a chance to represent Canada at the World Junior Championships. Ashton started out his professional career in 2011-12 with the AHL's Norfolk Admirals. He had a very productive rookie season putting up 35 points in just 56 games.
In 2012 the Leafs acquired Ashton in a trade with the Lighting for Keith Aulie. After his solid rookie AHL season, the Leafs had every right to be excited about what Ashton could bring to the table. As it would turn out, he pretty much brought absolutely nothing. Ashton lasted three seasons with the Leafs organization where he only recorded three assists in a combined 54 games with the team. To makes matters worse, Ashton's time with the Leafs was marred by the fact that he was suspended twenty games for substance abuse.
5 Best: Mats Sundin
Playing in a hockey crazy city like Toronto comes with a ton of pressure. When Mats Sundin arrived in Toronto in 1994, the pressure was tenfold. This was because in order to acquire the talented Swede from the Quebec Nordiques, the Leafs traded away one of the most popular players in team history in Wendel Clark. The trade ended up being one of the best ever in franchise history. For over a decade, Mats Sundin was the Toronto Maple Leafs.
Sundin would go on to lead the team in points in all but one of his 13 seasons in a Maple Leafs jersey. Although Sundin was never was able to bring another Stanley Cup to the city of Toronto, he put his heart and soul into every shift he played with the team. When he left Toronto in 2008, he ranked first in Maple Leafs history with 420 goals and 987 points.
3 Worst: Don Edwards
Don Edwards began his NHL career in the late 1970s as a member of the Buffalo Sabres. The former fifth round draft pick defied the odds by making the Sabres roster in his very first pro season. After a solid rookie season, he played an incredible 72 games in his sophomore year. For the next few seasons, Edwards became one of the top goalies in the entire league.
By the time Don Edwards had joined Toronto in 1985, his play had been in decline in recent seasons. He had spent the previous three seasons with the Calgary Flames where his numbers were nowhere near as good as they were in Buffalo. Despite his recent struggles, the Leafs signed him to a three-year contract. Edwards would last just one season, where he posted the worst numbers of his career which included 4.78 GAA, and a .860 save percentage. Toronto bought out the remaining years of his contract, and at the only the age of 31, Edwards was out of the game.
2 Best: Darryl Sittler
Darryl Sittler (Pictured Center) had a slow start to his NHL career with the Maple Leafs, recording just a combined fifty points in his first two seasons. However, his third season in 1972-73 was a breakout year for him as he led the team with 77 points. From that point on, Sittler only got better as a player. He would go on to play parts of 12 seasons with the Leafs where he recorded at least ninety points in five different seasons.
Sittler had some great offensive achievements with the Toronto, but everything pales in comparison to what he did on the night of February 7, 1976. In a game against the Boston Bruins, the Leafs would win the game by a final score of 11-4. Sittler would end up setting an NHL record with ten points that night, a record that most likely will never be broken. Darryl Sittler would go on to have many special performances throughout his time in Toronto, including once scoring five goals in a single playoff game. It was moments like these that solidified Sittler as not only the greatest Toronto Maple Leaf since 1967 but possibly the greatest of all-time.
1 Worst: Brett Lebda
Brett Lebda had a solid college career at Notre Dame before signing with the Detroit Red Wings as an undrafted free agent in 2004. After spending just one season in the minors, the defenseman became a regular in the Red Wings lineup. While his play was nothing fancy, he was a solid bottom pairing defenseman for Detroit.
After playing parts of five seasons and winning a Stanley Cup with the Red Wings, Lebda signed a free agent with the Leafs in 2010. Although he signed a two-year contract with Toronto, his stay just lasted one miserable season. He only managed to get into 41 games with the team, and registered a measly four points. His most embarrassing stat of all was when he somehow managed to finish with a minus three rating, in a Leafs 9-3 win over the Atlanta Thrashers.
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