The mistakes Burke made
1. Overrating how good his team was
Burke will tell you otherwise, but had the Leafs' brass known this team would struggle as much as it has this season, they never would have dealt two first-round picks and a second-rounder for Kessel.
Last fall, Leafs management believed that, with their off-season additions, they could win enough games to crawl into a playoff race, or at the very least, finish ahead of five other teams in the standings and out of the lottery.
However, since the lockout, the NHL has been a volatile league, with little separating the good from the great and the bad from the horrible. (The Colorado Avalanche are a perfect example given their crash and unlikely rebirth in the past 12 months.) While it was reasonable to project in September that the Leafs could repeat their mediocre 2008-09 campaign and finish about 24th overall, it was always a gamble that a team with little offensive production and questionable goaltending wouldn't hit a rut and bottom out.
They did, almost immediately, with a 3-11-6 start, and while he can't admit to it now, dealing that pick was a bet Burke lost.
2. Sticking with Vesa Toskala in goal
The Leafs were dead last in team save percentage (.885) in Burke's first season, posting one of the worst marks of any team in the past decade, and the GM had a good, long look at Toskala's continued struggles between the pipes.
With an overabundance of cheap options in goal in free agency last summer, however, Burke kept Toskala and signed a green rookie in Jonas Gustavsson as his backup.
By the time the Leafs finally threw in the towel on Toskala in January, the damage was done, and Toronto will end the year in a familiar spot: last in the NHL in team save percentage (.892). Goalies they could have signed for less than $2-million (all currency U.S.) a season, like Colorado's Craig Anderson, are among the league leaders.
Alternatively, the deal for Jean-Sébastien Giguère from the Anaheim Ducks had been discussed as far back as last summer and would have made a big difference had it been made earlier in the year. Goaltending has gone from a weakness to a strength the past two months, and Toronto's record has improved considerably with Giguère (12-10-3).
3. Trading all those picks
If Burke was hell-bent on moving a first-round pick or two to fast-track his rebuild, he had better options than what he chose.
For one, the Leafs could have landed Kessel via an offer sheet for $5.4-million a season, his current salary. Compensation would have been three picks - a first-rounder, a second-rounder and a third-rounder - and Toronto would have kept its 2011 first-round pick.
(Burke has an aversion to offer sheets stemming from the time the Edmonton Oilers snatched Dustin Penner from his Anaheim Ducks, and that likely prevented him from pursuing that course.)
Burke could have alternatively made this year's first-round pick conditional - or "lottery protected," as is often the case in the NBA. The condition could have been as follows: If Toronto finishes in lottery position, instead of giving up the 2010 and 2011 first-rounders, make it 2011 and 2012.
If Boston wouldn't sign on those terms, go the offer-sheet route, or don't make the deal.
4. Dedicating big dollars to Mike Komisarek
Burke spent roughly $11-million in free agency last summer, with the bulk of that dedicated to Komisarek, a defensive defenceman coming off a shoulder injury who had never had more than 19 points in a season.
Despite the fact players with similar skill sets signed deals in the $1.9-million to $3.4-million range (think Greg Zanon and Rob Scuderi, among others), Burke gave Komisarek $4.5-million a season for five years on July 1, making him one of the 25 highest paid blueliners in the league this season.
5. Keeping Tomas Kaberle
The long, sorry saga of trying to trade Kaberle is a couple of years on, but it's unlikely his value has ever been lower. While he produced offensively earlier in the year, he has also been a liability on defence with one of the worst plus-minus ratings in the league (minus-18) despite not facing opponents' top lines.
While it's widely accepted Burke will deal Kaberle this summer with one year remaining on his contract, his profile around the league has been hurt by his play this season. The Leafs may no longer be able to command the type of draft pick and/or top-six forward they had hoped for in a deal.