Among the names of the players and teams that the Stanley Cup consists of, is a black mark that reminds us of the very real greed and politics that influence professional sports. In between the cup wins of Tampa Bay and Carolina the words ‘2004-2005 SEASON NOT PLAYED’ can be found.

After that dreadful lockout season, a new system was born. No longer could the rich teams buy championship teams that would crush the lower payrolls among the league. Gary Bettman sought to create a system that would create parity around the league, thus giving birth to the Salary Cap Era.

The man behind the wheel at the time was no other than the much maligned John Ferguson Jr. To most hockey savvy Torontonians, the former general manager is known for some questionable trades (Raycroft for Rask for one), letting go pf some quality draft picks (two firsts and three seconds) and handing out some pretty ugly contracts (see the article that follows). More cringe worthy contracts would be found in the season that followed as GMs Cliff Fletcher, Brian Burke and Dave Nonis, also handed out some questionable deals.

Over the course of this article, you will notice the trend of the Leafs shooting themselves in the foot by awarding the wrong people with the wrong value and term of contract. This season, the Leafs are paying over $13 million in contracts for players either bought out, injured, or retained salary.

The ball now lies in the hands of Brendan Shanahan’s along with his crack team of Lou Lamoriello and Kyle Dubas. With a history of poor deals, trades and seasons to dwell on, Leaf fans are hopeful this is the team to right the ship and make the “centre of the hockey universe” a winner again.

Until then, here are some post lockout contracts that didn’t pan out for the Blue and White.

15. Eric Lindros 

via metronews.ca

via metronews.ca

Signed by John Ferguson Jr.

After the lockout, the Leafs brought the Big ‘E’ over from Free Agency. Being one of the greatest players not in the Hall of Fame, Lindros only managed to obtain a small one year deal worth $1.55 million. His history of dominance in the NHL coupled with a long history of concussions made it a low risk and high reward situation. Fans were skeptical that he would be able to play 82 games and were proven right after he only played 32 games that season. He retired the following season with the Dallas Stars after finishing another shortened season.

14. Joffrey Lupul 

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Signed by Dave Nonis

When Dave Nonis handed out a five year, $26,250,000 contract to Joffrey Lupul, he was seeing some very good success alongside Phil Kessel after coming over to Toronto during the 2010-2011 season. The next year, Lupul was scoring over a point a game, and in the truncated season that followed he would continue that pace. When you consider his history of poor health and the fact he missed 48 games over those two seasons however, there was a lot of risk in signing the aging winger. Now with three years left on his deal, his production is noticeably slowing as Mike Babcock has him relegated to third line duties… when he’s available.

13. Darcy Tucker 

via andrewgforbes.wordpress.com

via andrewgforbes.wordpress.com

Signed by John Ferguson Jr.

The feisty Leaf winger wore his heart on his sleeve and played the game with the grit that drew the love of Toronto fans. His numbers weren’t poor and his contract was arguably very solid, but in the second year of his four year, $12 million contract, Tucker was becoming prone to injury and was perceived to be losing a bit of his “it factor.” The team bought out the remaining years on his contract, but the memory of Darcy trying to fight the entire Senators bench would stay with fans longer than the $6 million the Leafs were on the hook for, over 6 years, after buying him out.

12. Phil Kessel 

Tom Szczerbowski-USA TODAY Sports

Tom Szczerbowski-USA TODAY Sports

Signed by Dave Nonis

When you sign an elite-scorer like Kessel for eight years, you hope he becomes the cornerstone of your franchise. Instead, he was branded (by a large portion of Toronto fans) as a ‘coach-killing, hotdog eating, one dimensional, disappointment’. As it stands now, the Leafs will be paying $8,400,000 over the next seven years for the winger to play for the Pittsburgh Penguins. You can’t blame Nonis for locking up a player with his type of elite skills and stats for the length and term that he did. Phil Kessel was, and still is, an elite force in the league, but the Toronto market and the team around him perhaps wasn’t the best fit for Phil.

11. Dion Phaneuf  

Kyle Terada-USA TODAY Sports

Kyle Terada-USA TODAY Sports

Signed by Dave Nonis

On the eve of the 2014 Winter Classic, Dave Nonis handed out his first seven year contract in his Toronto assignment. Perhaps in all of Leafs history, there is no captain who generates less cheers from the crowd and less respect among the fanbase. He is still a capable defenceman and appears to be winning over his head coach, Mike Babcock, but even Babs can see that he isn’t getting a seven million dollar performance most nights. With five years remaining on his deal (after this year), the Leaf’s would be hard pressed to move the D-man in a trade.

1o. Mikhail Grabovski 

via n1.by

via n1.by

Signed by Brian Burke

At $5.5 million a year, Grabovski would’ve been the highest paid Leafs forward in 2015 if they kept him around. Grabovski had some success with the Leafs before Brian Burke signed him to a five year, $27.5 million deal. After not meeting all of Burkey’s expectations in the years that followed, the Leafs exercised a compliance buy out for the speedy Russian centre. To say he left on bad terms would be an understatement as he made sure everyone knew Randy Carlyle was a “ F****** idiot” for not playing him on his top lines.

9. Colby Armstrong 

via hfboards.hockeysfuture.com

via hfboards.hockeysfuture.com

Signed by Brian Burke

Expected to be an elite third liner who could chip in on the offence, Brian Burke brought in Colby Armstrong with a three year, $9 million contract in July of 2010. He was to be somewhat of a posterboy for the grit and pugnacity Burke wanted his team to play with. When healthy, he seemed to jive well with the team, but he would soon fall victim to injury. Unfortunately, he never really fit in with the club and only managed to play in 79 games in his two seasons with the club, leading to a buy out before the last year of his deal.

8. Stephane Robidas 

John E. Sokolowski-USA TODAY Sports

John E. Sokolowski-USA TODAY Sports

Signed by Dave Nonis

The Leafs signed the veteran defenceman in the 2014 offseason after he suffered two broken legs and are now in the midst of suffering two more years of paying him $3 million per year. The hope was he would bring a veteran presence to a younger locker room, but his first season was met with sub par play and a season ending shoulder injury. After playing a few games in the pre-season, Robidas has yet to step on to the ice in the current Leaf season. Without a doubt, three years and three million dollars per is a lot of money for a veteran presence in the press box.

7. Bryan McCabe 

via rantsports.com

via rantsports.com

Signed by John Ferguson Jr.

Bryan McCabe had a big shot and the physical toughness that earned him a 5 year, $28.75 million contract after the 2005/2006 season with the club. He followed that season with a very decent 57 point season, but would decline fast in the years that followed. His perception of physical dominance was all but lost when he was rag-dolled in a fight with Zdeno Chara (not many can stand up to big Z) and his point production also declined. He only registered 23 points in 54 games in the second year of his deal that also saw him score a game winning goal for the Buffalo Sabres with three seconds left in a game… as a Maple Leaf. We all make mistakes. The Leafs traded him to the Florida Panthers where his numbers would get better, but the Leafs did not get much in return.

6. Jason Blake 

via dailyfaceoff.com

via dailyfaceoff.com

Signed by John Ferguson Jr.

After a 40 goal season with the New York Islanders, the Leafs pounced on the speedy 34-year-old, giving him a five year, $20 million contract. After a slow start with the club, he told the press that “the goals would come” and the Leafs fans waited. The only thing that came, however, was a 25 goal drop off from his All Star performance the previous year. Though he had some success, he only scored more than 20 goals in one of those years before being traded to the Anaheim Ducks, two and a half years into his contract.

5. Tim Connolly 

via windsorstar.com

via windsorstar.com

Signed by Brian Burke

An elite talent at times, but oft-injured and seen as a defensive liability. That was the Buffalo Sabre’s general perception of Tim Connolly before they let him go to Free Agency in 2011. It was clear Brian Burke didn’t share that perception as he decided to take out a flyer on him, offering him a 2 year, $9.5 million. Not even the Marlies could benefit from the 28 games he played in the second year of his deal. There. he would score 12 points which equates to him making $375,000 per point tallied with the Toronto farm team.

4. Mike Komisarek 

via cbc.ca

via cbc.ca

Signed by Brian Burke

Over his six years with the Montreal Canadiens, Mike Komisarek earned a lot of respect around the league as a solid, stay at home defenceman. He fit the Brian Burke mould of a shot-blocking, hard-hitting, tenacious defenceman and that earned him a five year deal, worth $4.5 million a season. Unfortunately his first season was cut short with a season ending shoulder injury and the rest of his tenure as a Maple Leaf wasn’t nearly as great as his time in Montreal. After making headlines on TMZ for allegedly punching a woman in a nightclub, the rest of his tenure with the club had him playing some games with the Marlies before getting bought out by the club.

3. Jeff Finger 

via mapleleafshotstove.com

via mapleleafshotstove.com

Signed by Cliff Fletcher

We all remember the joke. In the summer of 2008, Cliff Fletcher decided to give Toronto fans the ‘Finger’. After 94 games in the NHL, the Leafs brass decided his play was worth four years at $3.5 million. They wanted the shutdown defenceman to build upon his best seaso,n that saw him register 19 points and +12 with Colorado, but the only shutting down that would happen was to his NHL career. After two mediocre seasons with the squad, he became one of the highest paid players in the AHL.

2. David Clarkson 

Kim Klement-USA TODAY Sports

Kim Klement-USA TODAY Sports

Signed by Dave Nonis

When it came to the Free Agent Frenzy in 2013, David Clarkson was the Belle of the Ball. Leaf fans thought they were getting a gritty player with the ability to score thirty plus goals. He was the ‘Son of Clark’, put ‘71’ on the back of his jersey (A Wendel Clark reversal) and instantly drew the love of the fan base. who had been looking for the heart and soul that Wendel brought back in the 90’. He commanded a hefty 7 year, $36.25 million contract and the lofty expectations of the center of the hockey universe. His first season saw him generate more games missed due to suspension than points registered (11) with the Leafs. In the midst of his second disappointing season, he was then swapped for a player in Nathan Horton, who will likely never play hockey again.

1. Brian Burke, Dave Nonis, Cliff Fletcher and John Ferguson Jr. 

Bill Streicher-USA TODAY Sports

Bill Streicher-USA TODAY Sports

Since the salary cap came into effect, the Leafs have managed to make the playoffs only one time under the leadership of these four general managers. If these GMs did anything well (aside from a good trade here or there), it’s that they taught us all that big contracts and term aren’t to be handed out lightly, especially to players well in their thirties. They clog up your salary cap, become impossible to move and handcuff your development.

The Chicago Blackhawks and Detroit Red Wings have built contenders by drafting and drafting well, all while managing their cap situation well. It appears as though the Leafs could be on the right track with some great prospects coming down the pipe and a smart management team who will likely not make the same mistakes. It’s hard to predict what this club will look like in seven years, but knowing 2023 will be the last year they have to pay Phil Kessel $1.2 million, they have at least one thing to look forward to.

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