The Toronto Maple Leafs began the tear down and rebuilding of the sad-sack National Hockey League team by starting from the top – jettisoning star sniper Phil Kessel.

In a blockbuster deal Wednesday, the Leafs ended a tumultuous six-year marriage with the introverted Kessel by trading essentially the face of the franchise to the powerhouse Pittsburgh Penguins.

In return, the Leafs received only a collection of draft picks and prospects that they hope will help them begin the long road to respectability.

Just over a year ago, the Leafs brought in Hall of Famer Brendan Shanahan as president to shake up a team that has not won the Stanley Cup since 1967. And in May of this year, well-regarded Detroit Red Wing coach Mike Babcock was hired as Leaf head coach to expedite the rebuilding process.

After the Kessel trade, all that remains as an ugly reminder of his massive long-term contract is the 15 per cent – or $1.2-million a season – that the Leafs are on the hook for over the next seven years.

“The group that we assembled here wasn’t getting the job done,” Shanahan explained, a reference to Toronto’s 27th-place finish, its ninth season out of the playoffs in the past 10 years. “It wasn’t good enough. We’re here to build a team that’s capable of winning a Stanley Cup. There are no shortcuts to go around doing that.”

Trading Kessel for 18-year-old winger Kasperi Kapanen, 22-year-old defenceman Scott Harrington and a first-round pick on Wednesday didn’t make the Leafs better. Kessel has become one of the more dynamic offensive players in the NHL in Toronto, scoring more goals in his six years in the city than all but four other players in the league, using terrific speed and a lethal shot to beat goalies again and again.

But the Leafs’ brutal finish to the season – 11 wins in their final 51 games – soured Shanahan on the winger. Kessel struggled late in the year, scoring only twice in 21 games, and drew considerable criticism for everything from his attitude, work ethic and an unwillingness to interact with the media.

Shanahan believed he had to make the deal in order to both change the culture of a losing franchise and to cashout a soon-to-be 28-year-old for younger assets to build around.

It’s a process that could take three to five years – if it works at all – prolonging the agony for a fan base that is now accustomed to the abuse.

The Kessel trade was by far the biggest news in what is typically one of the busiest days in the hockey world. Hundreds of players become available every July 1 when their contracts end, which creates bidding wars and complex salary-cap manoeuvrings across the NHL beginning at noon EDT.

The 2015 class of free agents was one of the weakest in the past decade, however, and few stars found new homes. The two Alberta teams made a couple of the day’s biggest signings, with the Edmonton Oilers adding much needed defenceman Andrej Sekera for five years at $33-million and the Calgary Flames adding Michael Frolik on a five-year, $21.5-million deal.

The free-agent class was weak primarily because teams have made considerable effort to lock up their stars on long-term deals in recent years, something that should have made Kessel a desirable commodity as one of the few high-end scorers available.

But his poor season combined with the seven years and $50-million remaining on his contract made the deal a tougher sell than Shanahan had hoped. Several teams asked the Leafs to keep more salary than 15 per cent, and Toronto had to absorb the contract of an unwanted player (Nick Spaling) in order to make the Pittsburgh deal work.

They also paid Kessel a $4-million bonus right before the deal was completed.

“This was the best deal we had,” Shanahan said. “This was really about us saying that we’ve got to build this thing the right away, through the draft with prospects.”

For Pittsburgh, the acquisition was a no-brainer. Kessel joins two of the premier talents in the league in Sidney Crosby and Evgeni Malkin and can fade into the background as more of a support player, both on the ice and off it.

“He doesn’t have to be the guy here,” Penguins general manager Jim Rutherford said. “We’ve got a bunch of them.”

The Penguins superstars are also a similar age and have similar long contracts. Their window to win a Stanley Cup is also in the immediate future, which is why they could afford to move a promising player such as Kapanen (last year’s first-round pick) and mortgage some of their future.

But the Leaf window remains on the distant horizon, years down the road, when all of the prospects and picks they have been accumulating become NHL players.

It’s unlikely any will be as productive as Kessel, who ended his tenure in Toronto with 181 goals in 446 games, a 33-goal pace per season.

The Globe and Mail
Published Wednesday, Jul. 01, 2015 1:01PM EDT
Last updated Thursday, Jul. 02, 2015 5:21AM EDT