8 Players The Maple Leafs Kept Way Too Long (And 7 They Should Have Never Let Go)

Life is pretty good for those that inhabit Leafs Nation these days. A recent and sudden surge back into Stanley Cup contention on the backs of young talents Auston Matthews, Mitch Marner and William Nylander has brought about a bright future even amidst a dodgy past. Recent odds in Las Vegas even projected the Leafs, less than two years removed from owning the league's worst record, to be the prohibitive Cup favourite at this early stage of the season.

While Leaf fans undoubtedly want to focus on the plentiful good news surrounding the club, they haven't achieved anything beyond last spring's first round playoff loss to the Washington Capitals yet. Plus, to truly appreciate their lofty present standing, it is worth remembering some of the lowlights that plague a franchise still trapped in a 50-year Cup drought.

And so it is my duty to play the buzzkill role of identifying 15 costly personnel decisions made by the club. These include players that were kept in blue and white too long, as well as others who didn't stick around long enough. Bear in mind that these must be players who donned a Leafs jersey rather than prospects or draft picks who debuted elsewhere. In other words, it's the rare Leafs list that won't bemoan the trading away of Tuukka Rask or the pick that would become Scott Niedermayer.

17 Stayed Too Long: Bryan McCabe

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The story of Bryan McCabe in Toronto is a familiar one to Leafs fans. The blue liner became a fan favourite as a high energy player who would dish out big hits and chip in on offence from time to time. But popularity soon gave way to greater attention and heightened expectations, with McCabe's flaws coming under scrutiny while unrealistically being viewed as a top pairing d-man.

Expecting someone to be what they're not rarely ever ends well. Making things even worse for McCabe was the reality of being a mobility-challenged defenceman in an increasingly fast, wide open NHL. After years spent revelling in his hard-nosed play, fans soon grew tired of seeing speedy forwards blow by him. McCabe wound up spending seven seasons with the Leafs, although he probably would just as soon like to forget a few of them.

16 Left Too Soon: Darryl Sittler

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No, the Maple Leafs organization didn't exactly get short-changed on the production extracted from Darryl Sittler. Sittler ranks second in franchise history in both goals and assists, remaining one of the most celebrated Leaf greats to this day. When Sittler did leave Toronto, he was 31 and would only have another peak season or two left in him. So what places him in the "left too soon" camp?

The fact is, Sittler probably should have never left. It was the toxic atmosphere around the club, anchored by miser owner Harold Ballard that pushed him out. An increasingly sour relationship with Ballard and then-GM Punch Imlach prompted the long-time captain to rip the C off of his sweater when management traded his best friend Lanny McDonald to spite him. Later, the proud Leaf was made so miserable that he agreed to waive his no-trade clause in search of a fresh start elsewhere.

15 Stayed Too Long: Tomas Kaberle

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Tomas Kaberle was the rare homegrown success story in Leafs Nation during the late 1990's and 2000's as a late draft pick who blossomed upon arrival from the Czech Republic. The smooth-skating puck mover remained a stalwart on the Toronto blue line for 12 seasons, climbing all the way up to eighth in career games played for the franchise. In the end, however, he may have played a few too many.

In 2008, less than three years before he would ultimately be moved to Boston for Joe Colborne and draft picks, Kaberle was set to be shipped out in an agreed upon trade with the Philadelphia Flyers for Jeff Carter and a first round draft pick. Then-interim GM Cliff Fletcher had a steal on his hands to nab a 23-year-old sniper, but Kaberle exercised his no-trade clause to scuttle the deal.

14 Left Too Soon: Alex Steen

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The early goings of the 2008-09 NHL season were not a period of notable optimism for the blue and white. The Leafs had missed the postseason by 11 points the previous season and had opened the new campaign with an underwhelming 7-8-5 record. For some reason, interim GM Cliff Fletcher saw this as an opportune time to swap out two former first round picks for a veteran forward.

Suffice to say, Lee Stempniak's two-year career in Toronto was not particularly distinguished. The right winger netted 25 goals over two years, but failed to move the needle much before being shipped out again to Phoenix. Going the other way were Alex Steen and Carlo Colaiacovo. The 33-year-old Steen is now in his 10th season with the St. Louis Blues, where he has surpassed 400 points while serving as a two-way mainstay for the perennial playoff contenders.

13 Stayed Too Long: Shayne Corson

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From a purely emotional standpoint, it was hard to dislike Shayne Corson's arrival in Toronto. After signing a three-year contract in 2000, the Barrie, Ontario native was fulfilling a childhood dream, not to mention that of his late father, by suiting up for the blue and white. Personal stories aside, the cold reality of Corson's arrival was that the gritty forward was a 34-year-old without much left in the tank.

The one-time 30-goal scorer would only pot 27 total over his three years in Toronto. For a guy prone to bouts of anxiety and panic attacks, the pressure cooker of Leafs Nation proved tough to handle, particularly as fans grew frustrated with Corson's lack of production. He didn't exactly endear himself to the Toronto faithful upon exit, as he responded to being a healthy scratch during a 2003 playoff series by 'resigning' from the club.

12 Left Too Soon: Steve Sullivan

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Toronto Maple Leafs management has a long and rather ugly history of practicing poor asset management, not the least of which was demonstrated in the handling of Steve Sullivan. The small, speedy forward was a significant part of the return in the Doug Gilmour trade and then enjoyed a breakout 1998-99 campaign with 20 goals and 40 points in 63 games. Seven games into the following season, however, and he was cut by the team.

Then just 25, Sullivan would land in Chicago and score 103 goals over the next four seasons of what would be a 16-year career. In fact, during a 1999 to 2003 stretch in which he averaged 65 points per year for the Blackhawks, only one Leaf not named Mats Sundin (Alex Mogilny) reached the 65-point plateau.

11 Stayed Too Long: Aki Berg

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A perennial whipping boy in Toronto, Aki Berg was unfairly burdened by the expectations associated with being the third overall pick in the 1995 NHL Draft. While never living up to his lofty draft slot, the veteran blue liner of over 600 NHL games was perfectly adequate as a fifth or sixth defenceman, albeit playing in a market that expected more.

Even so, Berg was never going to find his way back into the good graces of Leafs fans, which is why it was a little perplexing to see him stick around as long as he did. His 325 games played as a Leaf outnumbered those of more celebrated teammates like Gary Roberts and Curtis Joseph, and doesn't trail Doug Gilmour by much. Once his lengthy tenure in Toronto came to an end, so too did his NHL career, as he returned to Finland.

10 Left Too Soon: Rick Kehoe

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It is hard to lash out too harshly against a club that lost a talented player on account of a trade request, but it's equally difficult to ignore the fact that the Maple Leafs got rid of a player who scored 33 goals at age 21 while getting next to nothing back. In his first full NHL season, Rick Kehoe was the Leafs' second-leading goal scorer while averaging nearly a point per game. Even more exciting for Leafs fans, he looked poised to form a potent one-two combination with 22-year-old Darryl Sittler.

Instead, Kehoe grew disenchanted taking a back seat to new arrivals Lanny McDonald and Inge Hammarstrom on the depth chart and asked for a trade. He was traded to Pittsburgh in exchange for draft bust Trevor Johansen and Blaine Stoughton, who would only go on to big things when he left Toronto. Kehoe, meanwhile, enjoyed nine consecutive seasons in Pittsburgh of 27 goals or better, including a 55-goal outburst in 1980-81.

9 Stayed Too Long: Jonas Hoglund

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A popular joke amongst Leaf fans in the early 2000's focused on the team's inability to flank star centre Mats Sundin with any capable wing help. More often than not, Jonas Hoglund was the punch line to those jokes. While Sundin's countryman produced four perfectly adequate seasons in Toronto, a first line winger he simply wasn't.

For Hoglund, a 29-goal debut season in Toronto may have proven more of a curse than a blessing. Nothing excited Leafs fans more than seeing a player toil in Montreal, only to become an instant success in Toronto. That production, however, would not be matched in any of the three following seasons, with Hoglund being accused of failing to take advantage of Sundin's elite passing and play-making. Perhaps he was a decent player who was never meant for such a prime role.

8 Left Too Soon: Randy Carlyle

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For most Leaf fans, Randy Carlyle was the coach who engineered their team's unlikely playoff trip - and collapse - against the Boston Bruins in 2013 before his "my way or the highway" approach alienated players and expedited his departure out of town. Many years before his coaching career began however Carlyle was a talented blue liner drafted by the Maple Leafs.

As a player, Carlyle would go on to play over 1,000 NHL games, winning a Norris trophy and appearing in an All-Star Game along the way - just not with the Leafs. Toronto opted to package him with George Ferguson for veteran blue line help in the form of Dave Burrows. Carlyle would record 21 goals and 62 points over the following two seasons in Pittsburgh, or more than double what Burrows would produce during his Toronto tenure.

7 Stayed Too Long: Wendel Clark

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The notion that Wendel Clark stuck around too long is technically untrue. After all, Leaf fans were stunned by his initial departure from the Buds as part of the blockbuster trade that landed Mats Sundin. But to put sentimentality aside for a moment, the Leaf legend's second go-around with the club - one that came less than two years after the Nordiques trade - might have been a mistake.

Clark did post 30 goals in his first full season back, but unfortunately it marked the same amount of wins that the struggling Leafs managed that year. Unable to really help the team, his production dwindled to just 12 goals in 1997-98 before leaving once again as a free agent. The cost of the Clark reunion? The former No. 1 overall pick was acquired from the Islanders for a package that included young, talented defenseman Kenny Jonsson and the first round pick that would be used to land Roberto Luongo.

6 Left Too Soon: Russ Courtnall

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Mention the name John Kordic to Leaf fans of a certain age and it will invariably bring to mind less than pleasant memories of the rather one-sided trade that saw a 23-year-old Russ Courtnall shipped to Montreal. Although small at 5'11", Courtnall had already proven himself to be a bona fide scorer at the NHL level, recording three 20-goal seasons in his first four full campaigns as a Leaf. Then Toronto opted to ship him out for an enforcer.

Quite simply, Courtnall went on to big things and Kordic did not. A well-traveled player who suited up for six different franchises during a 16-year career, Courtnall would produce six 20-goal campaigns after the trade, including a 36-goal season with the Minnesota North Stars. Two years later, he would go from North Star to All-Star.



3 Stayed Too Long: Joffrey Lupul

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Joffrey Lupul remains a Toronto Maple Leaf in only the most technical of senses at this point. The oft-injured veteran forward last suited up for the blue and white on February 6, 2016 and has since been cast away to a strange netherworld where he is being paid to stay far away from the club and, evidently, let his contract expire.

It wasn't always this way. The one-time first line scorer, who arrived from Anaheim in a steal of a trade that also brought Jake Gardiner in exchange for Francois Beauchemin, managed 147 points over his first 179 games in Toronto. Over his last 101 games with the club, however, Lupul only recorded 35 points. Even if the 34-year-old enjoyed a complete return to health, it isn't easy to see where he fits within a stacked roster that has moved on without him.

2 Left Too Soon: Bernie Parent

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It's tough for most old time NHL fans to picture Hall of Fame goaltender Bernie Parent in anything but Philadelphia Flyer orange. But Parent actually spent a season and a half - on the cusp of his prime, no less - with the Maple Leafs in between stints in Philadelphia. The Montreal native posted some impressive numbers between the pipes, albeit with underwhelming win/loss numbers on pretty bad Leafs teams. But that wasn't where his story ended.

Though his talent was clear, Parent angered Leafs management by openly flirting with the NHL rival WHA. As a result, he was traded back to the Flyers just two years after being acquired from the same team. The rest, as they say, is history. Parent's second tour of duty in Philly would bring two Stanley Cups, two Conn Smythe playoff MVP awards and two Vezina trophies awarded to the league's top goaltender.

1 Stayed Too Long: Mats Sundin

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He never grew into the cult hero and fan favorite that Doug Gilmour and Wendel Clark were, but Mats Sundin still holds a special place in the annals of Maple Leaf lore and his legacy with the club cannot be tarnished. The Swedish center remains the franchise leader for goals scored and total points while playing 981 games in blue and white. But did he really need to stick around for all of those 981 games?

Towards the end of his Leafs tenure, Sundin was an ill-fitting holdover as a veteran on a team that needed to turn the page and get younger to move forward. However, as a member of the so-called 'Muskoka Five', a quintet of no-trade clause-bearing Leafs who were content to stick it out in Toronto rather than chasing a ring, he wasn't anxious to leave. This made for a long and awkward goodbye, finally culminating in a free agency decision to sign in Vancouver, leaving the Leafs with no assets coming out of his exit.

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