Toronto Maple Leafs v Boston Bruins

Judging a trade can be tricky business. It’s especially difficult to gauge winners and losers in a trade when the parameters involved offer varying degrees of benefit to the parties involved.

Personally, when it comes to measuring trade value in the immediate versus the longrun, I like to think about the Todd Van Poppel rookie card I swapped back in 1991. Van Poppel was supposed to be some kind of pitching phenom. I was too young at the time to understand or investigate why such sentiment was so popular, but I bought in. I scored a Van Poppel rookie card in a pack of Score baseball cards one afternoon. Knowing that such a card was a valuable commodity at the time, I used it to complete my set of 1990-91 Upper Deck hockey cards. Jeremy Roenick’s rookie card was featured in said set, and it just so happened to be the final piece of cardboard I required to complete my collection.

One afternoon, at the age of 11, I wandered in to my local card shop and presented the owner with my Todd Van Poppel rookie card. I told the man at the counter that all I wanted was the 1990-91 Jeremy Roenick card. I can’t recall what the value of these cards were at the time, but I know that this older gentleman looked at me and didn’t think twice about ripping me off. We had a deal. I had my Roenick rookie card to finish off my inaugural Upper Deck hockey set, and card store guy had his 25th Van Poppel rookie to add to his collection for the purpose of cashing in at the end of Van Poppel’s illustrious career.

Todd Van Poppel flamed out famously in the Majors. My 1990-91 Upper Deck hockey collection sits in a Rubbermaid container in my parents’ basement and I’ve seen its current sale value as low as $3.99 and as high as $19.99. Whatever the case, I won that trade, but it wasn’t a certain victory until four or five years after the fact.

This may not seem relevant at all here on Backhand Shelf, but it’s remotely relevant when we consider the Phil Kessel-for-Maple Leafs draft picks trade. Brian Burke gambled when he shipped three draft picks to the Boston Bruins in exchange for Phil Kessel back in 2009. He gambled that the pieces already existing on the Maple Leafs roster before he took over, combined with the free agents he had brought in, would make for a legitimate contender with the addition of Kessel. It didn’t work out right away, but here we are looking at a Game 7 between these two teams nearly five years after the fact. Brian Burke is no longer present in this picture, but his finger prints are smeared all over it.

Below is a timeline of the Kessel trade and the events that took place in its aftermath, complete with facetious judgment on who held the upper hand at the time.

September 18, 2009: The Toronto Maple Leafs acquire Phil Kessel from the Boston Bruins in exchange for a 2010 and 2011 first round draft selection and a 2010 second round draft selection. Kessel, along with Brian Burke’s offseason acquistions Mike Komisarek, Garnet Exelby, Jonas Gustavsson, and Colton Orr, immediately vault the Maple Leafs into contender status in the Eastern Conference. Advantage: Leafs

October 24, 2009: With Kessel beginning the season on injury reserve, the Maple Leafs get off to a horrendous 0-7-1. The Bruins’ impending first round draft selection suddenly looks like it may fall into the top 15. Advantage: Bruins

November 3, 2009: Kessel makes his season debut with the Leafs. Toronto loses to Tampa Bay in overtime by a final score of 2-1. Kessel is healthy and it’s still early enough to salvage the team’s season. Advantage: Leafs

January 14, 2010: The Toronto Maple Leafs hold a 15-23-9 record, the first round pick flipped to Boston is beginning to look like it could end up being high enough to land Taylor Hall or Tyler Seguin. Brian Burke meets the media, via the Globe and Mail:

“We said ‘what if, okay so what if it’s Tyler Seguin or Taylor Hall?’ What if it is?

We were prepared to make that [trade] We got a 21-year-old who scored 36 goals in the NHL last year. I’ll make that trade again today. If it turns out it’s the end of the year and it’s a lottery pick, I’ll still make that trade.”

Burke and co. may have said ‘what if’, but this is hardly where anyone envisioned the team sitting halfway through the season. Advantage: Bruins

April 10, 2010: The Boston Bruins finish the season as the sixth seed in the Eastern Conference. The Toronto Maple Leafs are dead last in the East. Phil Kessel registers his second straight 30-goal season; the draft lottery results await. Advantage: Push

April 13, 2010: The Edmonton Oilers win the NHL draft lottery, the Boston Bruins land the second overall selection via the Toronto Maple Leafs. The Taylor vs. Tyler debate rages on. Advantage: Bruins

June 25, 2010: The Bruins select Tyler Seguin second overall and Jared Knight with the Leafs first and second round picks . The Maple Leafs have a burgeoning elite scorer in Phil Kessel. Advantage: Push

October 15, 2010: The Maple Leafs are off to a 4-0 start, parade planning jokes run rampant. Kessel registers four goals and six points, Seguin logs approximately 12 minutes a night as a 19-year old. Advantage: Leafs

November 13, 2010: The Maple Leafs have lost 11 of their last 12 games and Kessel has cooled off considerably. The Bruins are winning, but Seguin appears lost on the ice most nights. Advantage: Push

December 9, 2010: Seguin is still adjusting to life in the NHL, to mostly underwhelming results. Still, he’s just 19. The Bruins are among the Eastern Conference’s hottest teams with 16-8-3 record. The Maple Leafs are 10-14-4 and Kessel has reached his second 7-game goalless streak of the season. A “streaky scorer” narrative is born. Advantage: Bruins

January 29, 2011: Phil Kessel is selected last in the inaugural NHL All-Star draft. Morons and idiots everywhere think this somehow reflects negatively on one of the league’s best goal scorers. Advantage: No one

February 12, 2011: The Leafs, trying to recover from November and December, watch Phil Kessel reach 14 games without a goal. The Bruins are 31-7-7 with a very talented, yet still wet behind the ears, Tyler Seguin developing on some carefully matched minutes. The Toronto media collapses in on itself. Advantage: Bruins

February 15, 2011: Kessel scores two goals versus the Bruins in Boston to help the Leafs to a 4-3 win. A hot finish could still propel the club to the playoffs, and deny the Bruins a second straight lottery pick gift. Advantage: Leafs

February 18, 2011: The Leafs traded Tomas Kaberle to the Boston Bruins for Joe Colborne, a first-round draft pick in 2011 and a conditional draft pick in 2012. The impact of sending all those picks to Boston for Kessel is lessened. Advantage: Leafs

April 9, 2011: The Maple Leafs finish the season on the outside looking in once again. Kessel notches his third consecutive 30-goal season with 32 goals and 64 points in 82 games played. Tyler Seguin doesn’t play a major role in the Bruins’ 46-25-11 finish atop the Northeast Division, and he figures to be a scratch heading into the post-season. Advantage: Leafs

April 12, 2011: The Bruins will select 9th overall at the draft in June with the Leafs pick to complete the trade. Advantage: Bruins

May 14, 2011: Seguin, after sitting out the first two rounds, makes his NHL Playoffs debut. He registers a goal and an assist in a loss versus Tampa Bay. Advantage: Bruins

May 17, 2011: Seguin carries the Bruins to a 6-5 win over the Lighting with two goals and two assits. Advantage: Bruins (Leafs fans are left with a terrible feeling in their stomachs)

June 15, 2011: Seguin hoists the Stanley Cup with the Bruins as a rookie. He failed to score again in the post-season following his four-point game. Advantage: Bruins (Leafs fans have regained their wits, yet it still stings)

June 24, 2011: The Boston Bruins select Dougie Hamilton with the ninth overall pick. If there were ever a name that would fit into Toronto Maple Leafs folklore, it’s gotta be Dougie Hamilton. Advantage: Bruins

2011 NHL Entry Draft - Portraits


Members of Canadian sports television’s hockey panels stoke the “who won the Kessel trade?” fire for the entire 2011-12 season. Kessel has a few good games in a row the Leafs won. Seguin is establishing himself as a solid NHLer, the Bruins won. Toronto media questions whenever Kessel goes a two games or more without a goal, the Leafs won. Seguin won a Cup as a rookie and the narrative-clenching types rejoice, the Bruins won. Kessel hangs in the NHL’s scoring race for most of the season, the Leafs won. Is there any end to this?

January 26, 2012: Phil Kessel is selected in the eighth round of the NHL All-Star Draft.

April 7, 2012: The Bruins finish first in the Northeast Division once again while the Maple Leafs miss the playoffs for the eighth straight year. Phil Kessel scores 37 goals and finishes with 82 points in 82 games. Tyler Seguin scores 29 goals and registers 67 points in his sophomore campaign. Kessel is clearly one of the most consistent goal scorers in the NHL, while Seguin’s possession stats add a coat of polish to his young career. Dougie Hamilton’s 72-point season in the OHL, although it’s junior, are a tough pill to swallow. Advantage: Bruins, ever so slightly


January 9, 2013: Brian Burke is relieved of his duties as general manager of the Maple Leafs. Many, rather lazily, point to the Kessel trade as his undoing. Advantage: Burke’s detractors (for the time being)

April 28, 2013: Phil Kessel leads the Maple Leafs back to the playoffs for the first time in nine years. The 25-year old winger brushes aside local media clowns suggesting that Dave Nonis should trade him and scores 20 goals and 52 points in 48 games. Seguin’s counting stats (16 goals and 32 points in 48 games) don’t take the leap that many had predicted/hoped for. Despite a step backwards on the scoresheet, Seguin’s possession totals are impressive once again. Dougie Hamilton has been anointed a Hall of Fame defenseman at the age of 19. Advantage: Leafs, ever so slightly

May 12, 2013: Phil Kessel scored what would eventually be the game-winning goal to stave off elimination in Game 6 of the Eastern Conference Quarterfinals versus the Bruins. Seguin, while playing very well, remains pointless through six games. Advantage: Leafs

May 13, 2013 (present day): Game 7 goes tonight in Boston. The next chapter of the Kessel trade debate looms.

Tyler Seguin is four years younger than Phil Kessel, and we probably haven’t watched his best hockey yet. Kessel, while it can be argued that his scoring peak is passing as we read this, is a fantastic NHL talent who ought to be in the conversation of the game’s top ten players. It’s far too early to pass definitive judgment on Dougie Hamilton, regardless of some NHL media types premature declaration. It’s almost as if judging this trade on the fly has been counterproductive. Whatever the case, it’s fun and it ain’t going away anytime soon.

At this point, it looks like both sides benefitted from this trade. The Bruins eschewed scoring ability when they were flush with it in favour of salary cap space. The Maple Leafs added a prodigious goal scorer when they were in a transition period. It very well could be another four or five years down the road before anyone can look back and say there was a definitive winner in this transaction. Yet here we are, declaring one with each passing goal, prolonged slump, run-in with a hot goaltender, and manufactured media spat.