Analysis: Kessel trade begins Maple Leafs' rebuild

Brendan Shanahan made his first major mark on the Toronto Maple Leafs roster on Wednesday, opening the door to the long-term, sometimes painful rebuild he knows the franchise needs to go through in order to once again become relevant in the chase for the Stanley Cup.

After spending months wielding his power mostly to build Toronto's front office and coaching staff, Shanahan, the Maple Leafs president, went to work on his roster rebuild by trading forward Phil Kessel to the Pittsburgh Penguins.

In trading Kessel, Shanahan opened $6.8 million in salary-cap space for the next seven seasons. The Maple Leafs retained 15 percent ($1.2 million) of Kessel's $8 million cap charge.

Kessel was the best trade chip Shanahan could play to start his rebuild if Toronto does not want to be in a win-now frame of mind, even after bringing in Mike Babcock as coach.

Pittsburgh, absolutely in win-now mode, was the perfect trade partner. The Penguins were desperate for a top-six scoring wing to pair with either Sidney Crosby or Evgeni Malkin. Kessel is a five-time 30-goal scorer who went through a slump at the end of last season, when he scored eight goals in his final 51 games. He finished with 25 goals.

The Penguins don't want to waste the rest of Crosby’s and Malkin’s best years as a perennial Stanley Cup Playoff failure. Kessel gives them a chance to make the most of those years, and that's why this trade works for Pittsburgh.

It works for the Maple Leafs because the return included prospects and the potential for a first-round pick.

Toronto landed forward Kasperi Kapanen, 18, who was Pittsburgh's first-round pick in the 2014 NHL Draft, defenseman Scott Harrington, who was Pittsburgh's third-round draft pick in 2011, and a conditional pick that could be Pittsburgh's first-round pick in either 2016 or 2017. Veteran forward Nick Spaling also is going to the Maple Leafs as part of the trade.

Defenseman Tim Erixon, forward Tyler Biggs and a conditional draft pick that could be Toronto's second-round pick in 2016 or 2017 went to Pittsburgh in the trade with Kessel.

Toronto used some of the immediate cap savings from the trade to sign forward PA Parenteau to a one-year contract that TSN reported is worth $1.5 million.

Parenteau is likely seen inside Maple Leafs headquarters as a either a short-term replacement for Kessel or trade bait for more picks and prospects before the 2016 NHL Trade Deadline.

In fact, he's probably both. So is Spaling, to a lesser degree. He is signed only through the 2015-16 season. It's hard to imagine his future in Toronto extending beyond that, or even through all of next season.

If nothing else, the Kessel trade from Toronto's perspective is about the cap room and flexibility it gains.

The Maple Leafs need flexibility more than they need Kessel at this point, because this trade is about way more than the 2015-16 season; it's about the six seasons to follow as well.

Meanwhile, Kapanen joins forwards William Nylander, Mitchell Marner and Brendan Leipsic in Toronto's growing pool of top forward prospects.

Kapanen came to North America at the end of last season and played in the Calder Cup Playoffs with Wilkes-Barre/Scranton of the American Hockey League.

Harrington gives the Maple Leafs more depth on defense, an important asset in any rebuild because depth allows them to A) improve and B) make trades to improve quicker.

Look at the Columbus Blue Jackets as an example. The Blue Jackets have been adding to their depth of picks and prospects for years. They used some of it Tuesday to acquire Brandon Saad from the Chicago Blackhawks.

Giving up a conditional second-round draft pick and retaining 15 percent of Kessel's salary are necessary evils in order to make the trade happen. Nothing is perfect.

Shanahan's hope has to be that the $1.2 million retained on Kessel won't matter in three years because the cap will be higher and the Maple Leafs roster will be more balanced with younger players (Kapanen, Nylander, Marner, Leipsic, future first-round picks) contributing on cheaper contracts.

It's possible that James van Riemsdyk and Nazem Kadri, who is a restricted free agent, could also still be around as the rebuild hits its stride. Van Riemsdyk is 26. Kadri will be 25 when the 2015-16 season starts.

It's also possible each could still be traded as Shanahan continues to frame his rebuild, because the Kessel trade should only be the start. There needs to be more dominoes to fall.

Defenseman Dion Phaneuf ($7 million cap charge for six more seasons), left wing Joffrey Lupul ($5.25 million cap charge for three more seasons) and center Tyler Bozak ($4.2 million cap charge for three more seasons) are definite trade candidates.

It's not that they're bad players; it's that they're on contracts that are unnecessary to Toronto during a rebuild. If Shanahan can get prospects or high draft picks for them either now or before the trade deadline, consider it a win for the Maple Leafs.

Shanahan has finally convinced the organization to relent on win-now expectations, allowing this deal to happen. But more trades like the one Shanahan made Wednesday will go a long way toward making the Maple Leafs good again.

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