Originally published in 2012

February 11, 2012 was a bittersweet night for Toronto Maple Leafs fans. Mats Sundin, the classy and consummate captain, was honoured with his #13 raised to the rafters. A familiar face in Tomas Kaberle took the ceremonial face-off. The Maple Leafs squad was horribly overmatched on the night, losing 5-0 to the Montreal Canadiens.

A number of Maple Leafs had poor nights, and the loss only served to heighten speculation that trades could be made at the deadline to bolster the team’s playoff chances. But with Sundin and Kaberle (and other former Maple Leafs) in the building, the minds of some fans turned back to February 2008 and the legacy of The Muskoka Five.

Things were different then. As much as fans wanted playoff hockey, a growing number saw an aging squad with little young talent in the organization. At the February 26, 2008 trade deadline, the team was 27-28-9 and some felt trades could net some good, young players to begin a rebuild. It was not to be.

The Maple Leafs made only three deals… Hal Gill, Wade Belak and Chad Kilger traded for three draft picks in 2008 (rounds two, three and five) and a fifth round 2009 pick. The team went 9-7-2 to close the season, missing the playoffs again. The focus fell onto five players who had no-trade clauses, given by former general manager John Ferguson Jr., and had refused to waive them. These players were thought of as the Maple Leafs’ most valuable commodities – trading one or all could potentially restock Toronto for the future. Mats Sundin, Tomas Kaberle, Darcy Tucker, Bryan McCabe and Pavel Kubina. They had come to be known as The Muskoka Five.

The District Municipality of Muskoka is a well-known as cottage country, a few hours north of Toronto. Huntsville and Gravenhurst are only two of the towns surrounded by innumerable lakes and waterways, forests and rocky shorelines. The moniker ‘Muskoka 5’ implied that veteran players in Toronto were too comfortable, content to play out the season and spend summers by the lake. No one could figure why anyone would pass up a chance to be playing for the Stanley Cup to stick around the Maple Leafs.

LeafsNation holds Sundin in the highest regard. There isn’t any lingering feeling that refusing a trade was disloyal. Sundin, as well as the other four veterans, had negotiated their deals in good faith, and were by no means obligated to accept a trade, no matter how the organization rationalized the request. Yet, looking at how these players eventually left Toronto, one wonders what may have been.

Darcy Tucker

Darcy Tucker had seen his production drop from 28 goals and 61 points in 2005-06 to 18 goals and 34 points for 2007-08. Still, his grit and experience could have proved valuable to a playoff team. He was bought out during Cliff Fletcher’s tenure as interim GM, and signed as a free agent with Colorado on July 1, 2008. After two seasons in Colorado, he retired. The Maple Leafs dealt with a $1 million cap hit from the buyout until the end of 2013-14.

Bryan McCabe

Bryan McCabe had been an offensive force, scoring 19 goals and 68 points in 2005-06, which netted him a five-year, $28.75 million deal. But, in the post-lockout NHL, McCabe had lost his physical effectiveness, and had difficulty adapting to the new obstruction rules. He posted 57 points in 2006-07, but in 54 games in 2007-08, he scored just five goals and 23 points with 81 penalty minutes.

On Sept. 1, 2008, Toronto paid McCabe a contractually-obligated $2 million bonus. On Sept. 2, he waived his no-movement clause and was traded to the Florida Panthers, along with a fourth round pick (Sam Brittain) in exchange for Mike Van Ryn. Unfortunate for the Maple Leafs, Van Ryn played only 27 games before retiring due to injury and surgery.

Mats Sundin

The Maple Leafs decided Sundin would not be in their plans going forward, and offered the Canadiens and New York Rangers the chance to acquire him before the trade deadline. Sundin made it clear he believed the Maple Leafs would make the playoffs, and would not accept a trade.

He became a free agent, and turned down a $20 million offer from the Vancouver Canucks as he contemplated retirement. He eventually signed with Vancouver on Dec. 18, 2008, and retired following the 2008-09 season.

Pavel Kubina

Pavel Kubina Signed as a free agent in 2006 for four years and $20 million – some felt too much for his 40 point contributions. Kubina, a powerplay specialist, was misused in Toronto, stuck behind the first powerplay pair of Kaberle and McCabe. Brian Burke eventually traded him to clear cap space, sending the defender to the Atlanta Thrashers with Tim Stapleton for Garnet Exelby and Colin Stuart on July 1, 2009. Exelby and Stuart were not factors with the Maple Leafs, though Burke used the cap room in part to sign Mike Komisarek and Francois Beauchemin. Kubina went on to play for the Tampa Bay Lightning.

Tomas Kaberle

The Tomas Kaberle saga played out over a few years in Toronto. Finally, on Feb. 18, 2011, Burke and Peter Chiarelli made a deal sending him to the Boston Bruins in return for Joe Colborne, a first round pick in 2011, and second round choice in 2012.

It was exactly the kind of deadline deal hoped for back in 2008. Toronto got a big centre who may lack a mean, physical presence, but has shown decent offense. Burke was able to package Boston’s first round pick and his own second to move up, selectng Tyler Biggs, another big forward who, it was hoped, would help solve some of Toronto’s ‘size up front’ issues. Boston’s second round pick was sent to Colorado for Kaberle’s replacement in John-Michael Liles. Kaberle won a Stanley Cup with Boston, signed a free agent contract with Carolina and was traded to Montreal.

It’s pure speculation as to what the Maple Leafs might have received if all five of these players were traded at the deadline in 2008. There weren’t many blockbuster deals that season, though some were significant. San Jose acquired Brian Campbell and a seventh round pick from the Buffalo Sabres for Steve Bernier and a first round pick. The Pittsburgh Penguins sent Colby Armstrong, Erik Christiansen, prospect Angelo Esposito and a first round pick to Atlanta for Marian Hossa and Pascal Dupuis. Colorado re-acquired Adam Foote in return for sending a first and fourth to the Columbus Blue Jackets.

Could the Maple Leafs have received similar returns for trades involving Tucker, McCabe, Sundin, Kubina and Kaberle? Quite possibly. It’s not as simple as saying if the player had waived his no-trade, the Maple Leafs would have made deals. True, Tucker and Sundin were nearing retirement, and McCabe seemed on the decline. Yet, as veterans with playoff experience, any one of them could have played a role for a team hoping to win the Stanley Cup. Perhaps no deals were offered because it was widely known the players would not make themselves available. Still, it’s reasonable to think a package of two players could have brought a prospect and a high draft pick, or that Sundin may have been worth a top-nine forward and a first-round pick.

Had Fletcher had the ability to make deals, the Maple Leafs may have been that much closer to building a playoff team. Interestingly enough, two of Burke’s major transactions saw the Maple Leafs acquire two players from the 2008 first round in Colborne (BOS – 16th) and Jake Gardiner (ANA – 17th). In the grand scheme, no amount of speculating will change the events of the 2008 trade deadline. Maple Leafs fans are long past holding grudges against these players. Still, some wonder what could have been if things had gone a little differently in the late winter of 2008.

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