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.

Comments (53)

  1. honestly, this was stupid. it was a win for the Bruins period. Tyler Seguin and Dougie Hamilton are still on entry level contracts, while the Leafs are about to unload 7+ million a year to keep Kessel Toronto. Not to mention without Kessel the Leafs would have finished last, landed Taylor Hall and in a full fledged rebuild probably landed another top flight prospect or two to build around.

    • Still nobody knows who won the trade but right now leafs are winning. Kessels points per game have been going up every year since he has got here, he is turning into a two dimensional player rather than just a sniper. Hamilton and Seguin are still unknowns, they could both flop of turn out very good but we can’t really say who won until they are all retired and who contributed more

      • Yep, votes not in for the winner of this trade yet. It’ll really depend on how Hamilton and Seguin develop. The Leafs got what they wanted, which is a star player…they just paid a higher price than they expected because they took a few years to make that big leap forward. Seeing them play though, I’m not 100% convinced that they are “for real”. I could easily see them on the outside of the playoffs looking in again next year.

      • This is one of the 3 worst trades in NHL history, your rose coloured glasses are not only amazing but histarical.

    • how has that worked out for edmonton? i’m even an oilers fan and i think what you said was pretty pie-in-the-sky.

      • I think that’s more a reflection of the people running the oilers than on anything else. They don’t seem to think defense is a position worth investing in

  2. Leafs win three Round 1 games and they now “won” the trade? Bruins WON the Cup. Pretty sure that’s the only thing people measure “winning” by.

  3. Well, given almost the entirety of Kessel’s deal was spent while the Leafs weren’t competitive, it seems like an odd time to mortgage futures for the present, no?

    The trade was wrong because of its timing, not who they acquired.

    • I don’t think I stated otherwise.

    • I guess it could be argued that, at this point, we can now resign him whereas we never would have signed him as an FA away from another team.

      However, that ability also brings with it the risk that we overpay Bozak (anything over $3M) as a way of keeping Kessel happy here as well.

      Looking at all the ways these decisions interact over multiple years really makes one appreciate the GMs who are consistently icing good to great teams.

  4. The team that gets the best player wins the trade and the Leafs got the best player. Combine Seguin, Hamilton, and Knight all you want.

    Kessel ended the season 6th in goals, 6th on points and Seguin was 59th, and has ZERO points in the playoffs as Boston will probably get eliminated by a team for which Kessel scored 2 game winning goals so far.

    Kessel has the most skill of all the players involved in the trade.

    LEAFS WIN! Thank you Boston.

    • +100000000000000000000000

      Best player means you won the trade. The best player, is unquestionably, Kessel. If Doug Hamilton turns into a top defender on a good team, AND Seguin improves considerably, maybe this will change. But Kessel is the best player right now, and it’s not really close at all.

      • The Leafs, and any sane Leaf fan, would deal Kessel for Seguin in a heartbeat.

        Would the Bruins turn down a Kessel for Seguin deal? Without a doubt they would hang up the phone laughing.

        Leafs won the trade? I don’t think so.

    • If you want to make that comparison, you need to factor in that this is Kessel’s 7th season & Seguin’s 3rd season.

    • Way to be completely and totally wrong…… Typical leafs fan

  5. I agree with John that this was stupid, but for a different reason. Before the draft lottery it was ‘push’? How the hell does that make any sense? Can you somehow explain how you had it as ‘win Bruins’ before the draft, only to switch to ‘push’ after drafting Seguin and Knight?

    Seems really stupid, and it can’t even be passed off as a typo. If you wanted to get technical as well, Knight was rated as a late first rounder, which means the Bruins got even better value.

    I’m not a Bruins fan at all, but I am a fan of comedy and good writing. This was an example of neither.

  6. Whenever i think of this trade I like to think if we still had Seguin were would we be, and I come to the conclusion we would be the Edmonton Oilers of the East. Always getting the first overall pick but sucking every year. Kessel helped get us into the playoffs, Kessel helped keep us in the playoffs. Now do you think Seguin could have done the same thing?

  7. Bruins win this trade – @John makes the best points.
    As soon as I read this,” 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”…I immediately dis-valued the rest of the article – why? – because its obvious this is written by another “Leafs fan” therefore the player evaluation and assessment abilities are not offered. It happens with lots of Leafs fans (not all – but lots), they know how to “observe” the Maple Leafs team, but cannot show the form for fair and proper evaluation….and this article is more proof of that.
    How does a team (Boston) give up a 36 goal scorer and still make the play-offs as the sixth seed and hasn’t yet cashed in or even displayed the players they received in the deal while doing so…the other team (Toronto) gains a 36 game scorer, displaying the player they received in the trade and doesn’t make the play-offs – but, its a push!??…come on! Make me laugh!

    • and you would be wrong. It was written by an Oilers fan

      • @pep – whatever – an Oilers fan, even worse….the writer has still shown NO player evaluations or assessment skills and that is how you “judge” something…and that was the point, way to miss it you clumsy fool

  8. December 10th 2010

    Phil Kessel plays over 24 minutes against the Atlanta Thrashers and registers an assist. Bruin’s GM Peter Chiarelli spills coffee on his favorite shirt which is now ruined.

    Advantage: Leafs

  9. “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.”

    Really?!?! Top ten *players*? Maybe top 10 forwards, but even that’s a stretch….Kessel is good and is definitely a star player, but I don’t see him cracking the top 10.

    In no particular order, Kessel is not as good as:

    St. Louis

    I put Kessel more in the Kopitar/Staal/Gaborik/Thornton/Elias/Parise category of second tier stars, though I’d take someone like Kopitar or Parise on my team before I’d take Kessel because they are much less one dimensional.

    I don’t want to take anything away from Kessel, he’s a good player. He’s just not top 10, even among forwards. Plus, I suspect Kadri could be outscoring him in a couple years.

    • …and I haven’t even mentioned Giroux, Perry, Getzlaf, etc yet!

    • @Devils win – your dead on!

    • Only 3 players in the league have scored more than Kessel in the last 3 seasons.

      But no, you’re right, he isn’t top 10.

      • There’s more to hockey than scoring. Apparently, you also want to prevent the other team from scoring goals. I know it’s not the ideal metric, but Kessel is -33 over those three years. Not all his fault obviously, but man, that’s brutal.

        • Not crucial to your point, but why does no one ever remember Toews?

          • Because he’s not flashy, he comes as a set with Kane (who is) and the team behind him is so deep?

          • Toews should have been on that top tier list. He may not score quite as much as some of the others, but he’s one of the most complete players in the game.

    • And those are only forwards, would you rather Kessel over Chara/Karlsson/Weber/Suter heck, even Subban?

  10. ” It’s almost as if judging this trade on the fly has been counterproductive. ”

    Yeah, this. And most trades that include good talent going both ways it takes years to know who “won” the deal.

  11. Everyone also forgets that with the cap space saved by trading kessel how the bruins also were able to acquire Horton (who has more consistency as a scorer), Peverly, and Chris Kelly… yeah not even comparable in terms of the trade. Burke is the most overrated GM of the modern era. On top of that trading huge picks for an elite winger without a top tier center always comes down to a stupid decision… that’s what made the trade that much worse. Leafs lost the trade that’s that people need to just accept it and be happy Burke is gone and won’t be overpaying for D or getting people like Connolly who don’t fit the team with any logic…

    • The Leafs had further to go than the Bruins. Boston had to unload Kessel, and they got good value for him. Both teams benefitted. If Toronto had kept their picks, they aren’t in the playoffs with Seguin and Hamilton. I’d say this trade was more of a win/win with Toronto getting a known commodity and Boston gettinga ton of potential that will likely amount to two at least above average players.

  12. “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.” If you have to use another trade to justify the Kessel deal, you’ve clearly already lost.

  13. “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.”

    I missed the comedic intent of this piece, didnt I?

  14. It’s hard to argue against a recent Stanley Cup championship team.

  15. Guys. Burke DID NOT trade Hamilton, Seguin and Knight for Kessel. He traded picks. At the time of the trade, there was no way of knowing who those picks would turn into.

  16. Kessel score !!!

    Where is Seguin ??

  17. 4-1 TO !!
    What a meltdown by the Bruins. They were leading 3-1, and now on the verge of losing 3 in a row. Gutsy win by the Leafs if they win tonight.

  18. WOW ! Those Bruins don’t know how to die !!!
    Hard to believe Toronto can come back and win in OT now…

  19. Phil Kessel ought to be in the conversation of the game’s top ten players?! lmao. Not even a top 10 player in his own division.

    • Seriously! What world is Scott Lewis living in that Kessel is a top 10 player in the league? Lemme guess, he lives in Toronto and only reads the local media?

  20. The purpose of every trade is to improve the teams chance to win the Cup. Seguin played a huge role in moving Boston past Tampa Bay in 11 playoffs to help the Bruins win the Stanley Cup. So Bruins win the deal. Kessel must win two Cups for Toronto to move ahead.

    For those that think the career stats are the final arbitrator, which I believe is only relevant if neither teams wins a Cup with the traded players, then wait until next year. If Seguin moves to center and he picks up his offensive pace and Hamilton becomes a top four defenseman next year then I think the deal is weighted heavily in Boston’s favor.

    However, I think Kessel and Seguin are genuinely identical players. Seguin could end up with the same fate as offensive gifted players such as Kessel/Joe Thorton/Craig Janny before him and then become trade bait for more draft picks if he does not pick up the 3rd defenseman role Julian requires of his centermen in the defensive zone.

  21. What a joke this is. You want to know why kessel is picked last every time he’s in the all star game? Because he’s a whiny bitch and a locker room cancer. Dougie and Seguin, or this primadonna loser? Come on now. Not even a discussion. Maybe if you had something relevant to say you’d have a job at a real website.

  22. Can you imagine kessels numbers if he had teammates like the bruins?? look what he has been playing with, now imagine what seguins numbers might look like with the leafs. the leafs are leaps and bounds better this year, but still something to consider. individual talent is fantastic, but is multiplied exponentially with the right line mates. wonder how seguin would flourish with bozak…

  23. Kessell remains an overall minus. Watch the last 10 seconds of his season.

  24. Bruins win hands down. Even if the Bruins didn’t get Tyler Seguin and Dougie Hamilton (who both project to be studs longterm), it’s still addition by subtraction.

    I don’t care if Kessel scores 50 goals a year for the next 10 years. The guy is a complete douche who plays selfish hockey, doesn’t play defense, and ruins team chemistry. There’s no place for a guy like that on a team that wants to compete for championships.

    And as you can obviously tell from watching that 2011 All Star game draft, the other players in the league can’t stand the guy. Just look at their faces while this is all going on, it is clear as day. And the Bruins players basically said as much after he left for Toronto.

  25. Whether the Bruins where serious in shopping around Tyler Seguin as possi le trade bait, or whether they where just trying to motivate the kid, one thing is clear. It should be very disconcerting to the Bruins having to go to those lengths to motivate the kid at a time in his career where he should be the most willing. It appears to me that while Seguin sits with a smirk on his face during the ever classy ” thank you Kessel” chants eminating from the Boston crowd, Kessel is developing way beyond him!

Leave a Reply

Your email address will not be published. Required fields are marked *