Bruins GM, Peter Chiarelli traded Phil Kessel to the Toronto Maple Leafs on September 19th, 2009 for a first and second round pick in 2010 and a first rounder in 2011. This past June he used those picks to select Tyler Seguin and London Knight centre, Jared Knight, but it seems Chiarelli wants to trade this year’s pick for someone who can help the Bruins right now.

Chiarelli was asked on WEEI radio in Boston if he’d consider trading Toronto’s first round pick in 2011?

"Yeah, I’d look at it, sure. I’ve had discussions involving that pick. I certainly would look at it. We’ve got a lot of assets, so that alone allows us to be creative also … there’s been one [deal] that we’ve thrown around here internally, I don’t know that I would do it but it’s something that warrants further discussion."

The last sentance is absolute brilliance on Chiarelli’s behalf.

How often have fans lamented that their GM could have gotten more in return had he waited longer when trading away an elite asset. Oiler fans, and even Kevin Lowe himself, have wondered if he could have received more for Chris Pronger in the summer of 2006. (Back then he got Joffrey Lupul, Ladislav Smid and two first rounders and a 2nd. Today the trade has evolved into Jim Vandermeer, Smid, Jordan Eberle, Martin Marincin and Cam Abney).

Opposing GMs and Bruins’ supporters wondered why then-GM, Mike O’Connell didn’t let the rest of the league know he was shopping Joe Thornton. The Bruins got fleeced in that deal getting only Wayne Primeau, Brad Stuart and Marco Sturm.

Clearly Chiarelli wants everyone to know where he stands with his "bonus" pick.

Chiarelli’s comments make it clear the Leafs’ pick is in play, but the subtle hint that he is close to a trade will surely get every other GM’s attention. Right now the pick would be the 5th choice, and at the very least it will be in the top-eight. Chiarelli is in a great position. His team is competitive, they already have a potential star in the system, Seguin, from the original deal, and now by going public he has increased his chances of maiximizing his return.

With 20 days until the trade deadline, this simple quote will have fans in every market looking at potential deals that could help their team.


While every team would love a shot at a top-five pick, the reality is there might only be a handful of teams who are willing, and able, to offer up a fair package.

Ottawa, Toronto, Florida, New Jersey, the Islanders and Edmonton are either completely out of the playoff race or hanging by a thread like Buffalo, Columbus and St. Louis. There are many teams currently in the hunt for the postseason, but would any of their GMs be willing to sacrifice this season for a potential top-five pick?

According to Capgeek  the Bruins can "currently" only acquire a max cap hit of $2.9 million, so I’m assuming any trade they make will see Michael Ryder, and his $4 million cap hit, as part of the package going the other way.

EDMONTON: The Oilers are currently 30th, and Steve Tambellini would be willing to part with a proven player to secure a second top-five pick in June. Ales Hemsky and Dustin Penner are the only Oiler veterans that would grab Chiarelli’s attention. Chiarelli acquired Nathan Horton and Gregory Campbell for Dennis Wideman and the 15th pick last summer, so it might take more than just Hemsky or Penner to get the pick. I suspect Chiarelli will want some sort of young prospect to be added to any deal.

OTTAWA: I know it would be within the division, but Chiarelli had no problem making the original deal with Toronto, so I don’t see him shying away if the Sens put a good deal on the table. Chris Phillips is the obvious name to be part of the package, but the Sens would need to add much more. Would Mike Fisher entice Chiarelli? I don’t think so, because he has two years left at $4.2 million, but Bryan Murray should be trying to save his job by securing another top-five pick.

New Jersey: Despite their recent hot streak, they aren’t going anywhere, and you wonder if Lou Lamoriello wants to break up his team rather than see them drop out of the bottom five. Lamoriello’s problem is he doesn’t have anyone who financially fits with the Bruins. Elias and Rolston are too expensive, and past their prime. Would Lou gamble and move Travis Zajak and David Clarkson? Zach Parise is up for a big raise, so the Devils need to make some room.

FLORIDA: Chiarelli and Dale Tallon made a deal at the draft, but I’m not sure they can come up with another one. The Panthers only have veterans Weiss, Booth, Olesz, Wideman, Kulikov, Clemmensen and Bryan Allen under contract for next season. Bryan McCabe, Cory Stillman, Radek Dvorak and Chris Higgins won’t get you a top-five pick. I don’t see Florida being a partner.

NY ISLANDERS: Garth Snow wouldn’t move John Tavares, and after that he doesn’t have anyone who could help the Bruins playoff push. Marc Streit and Trent Hunter are hurt, and the rest of the lineup is too inexperienced.

TORONTO: You know that Brian Burke will call Chiarelli and see if he is interested in making another deal, and if I’m Chiarelli I’d be all ears. I loved the deal he pulled off in 2009, but this time Burke’s cupboard is a tad bare. I’m sure Tomas Kaberle’s name will be first out of the gate, like it has been for the past two years. Would Kris Versteeg and Kaberle be enough?

BUFFALO: Sabres new owner, Terry Pegula, has a reputation of being very aggressive, but Darcy Regier hasn’t been that way in his tenure in Buffalo. The Sabres, after their win Tuesday, are only four points out with two games in hand. I’ll bet Pegula would rather make the playoffs this year, and if they stay close in the next few weeks, I think they’ll be more of a buyer than a seller.

ST. LOUIS: Most of the Blues best players are young, and moving one of them for another top-five pick would seem like a lateral move. The Erik Johnson trade rumblings don’t make sense, especially for a draft pick. I don’t think Andy MacDonald and Eric Brewer would entice Chiarelli and I doubt the Blues would move one of Oshie, Perron or Backes.

COLUMBUS: The Jackets have won three straight and are only four points behind 8th place Calgary with two games in hand. GM, Scott Howson’s job is on the line if he misses the playoffs, so I don’t see him trying to build a future that he won’t be a part of. I see Howson as a buyer, especially if the Jackets are within four points or less.


CALGARY: The Flames are 11-3-4 since Darryl Sutter resigned got fired, and suddenly in the playoff picture. Would Jay Feaster roll the dice and trade Robyn Regehr, and hope his team could still make the playoffs and get a top pick? The Flames are in a tough spot. They don’t have much depth in the farm, but would Feaster, or more specifically the owners, be willing to sacrifice a few home playoff dates for a potential franchise player? Tough call.

MINNESOTA: The Wild haven’t had a first round pick pan out since they took Brent Burns 20th in 2003. Since Burns they’ve drafte AJ Thelan (12th, 2004), Benoit Pouliot (4th, 2005), James Sheppard (9th, 2006), Colton Gillies (16th, 2007), Tyler Cuma (23rd, 2008), Nick Leddy (17th, 2009) and Michael Granlund (9th, 2010). Granlund and Leddy are too young to judge yet, but the rest are more suspects than prospect at this point. Chuck Fletcher needs to make a splash, and I wonder if Nick Schultz and Matt Cullen would get Chiarelli’s attention.

I’m sure many other GMs will contact Chiarelli to find out his asking price, and after yesterday’s comments I’m sure Chiarelli’s phone will be ringing frequently.

Letting the entire league know that  a potential top-five pick is on the market was a savvy move by Chiarelli, and I won’t be surprised if he ends up getting more than the supposed offer that is currently on the table. The only negative might be that the current GM that he is dealing with gets annoyed and backs out.

Chiarelli likely weighed the options and realized, that in this case, a public auction will garner a higher price than what he would have got in a silent one.

Brilliant move.

  • Ogden Brother Jr. - Team Strudwick for coach

    So what exactly happens when that pick ends up being closer to a top 10 pick than a top 5 pick? Not sure I really want to give up either Hemsky or Penner for a top 10. Too much risk. I do however think if we have any intention at moving either guy, that we do it this year.

    Very few guys around this year for trade and I really don’t want to risk Hemsky going down next season and getting nothing for him.

    • Jason Gregor

      Do you think Magnus Paajarvi has more upside than Penner or Hemsky? He was a 10th pick.
      Sure it might be a gamble, but if Penner or Hemsky don’t want to be here past next season, you need to get something for them.

      • That’s the crux of it really.

        Tambo needs to figure out before the deadline if Penner and Hemsky will sign extensions on July 1.

        If they will, they’re off the table baring a massive overpay.

        If they won’t, now is the time to move them, and you need to make sure you get a lot more than a deal centered around Nilsson or Lupul….

      • OB1 Team Yakopov - F.S.T.N.F

        Magnus might have more offensive upside then Penner, but I doubt he has more offensive upside then Hemsky.

        A quick scan of 5-10 picks however shows your odds of getting a player superior to Hemsky/Penner in those slots really isn’t that good.

        Of course your last sentence is key though, if they aren’t planning on sticking around (for a resonable price) then the team needs to get something for them… if a 5-10 pick is the best we can do, then so be it.

      • Ogden Brother Jr. - Team Strudwick for coach

        While I somewhat agree, I rather wait til the draft then when we know where everybody stands.

        We are in a very good position this year. There are very few UFA’s that are top 6 players, which generally means less players moved at the deadline and more teams desparate when their budgets are released after the season.

        By no means should we feel rushed the next few weeks in making a deal.

        • The Real Scuba Steve

          Waiting till the draft to trade Penner or Hemsky is a bad idea.
          On draft day, draft picks are over valued on trade deadline player are over valued.

          In other words you will be paying big amount to get a top 5 draft pick. Meaning Penner or Hemsky won’t get you too much in return.

          If our GM is done evaluating, make the trade before trade deadline.

  • It would be really nice if we could get more out of the Bruins if we have to bring Ryder back here. Jordan Caron could be big body RW, Adam McQuaid a big stay at home defender, or even Colborne for our big center.

    It might be asking too much, but I think we are dealing from a position of strength when our 2 players we are moving both have a year left on their deals. We haven’t been in the driver’s seat on many deals in the past.

  • Ender

    Interesting article, but I’d say Toronto is not really a trade possibility. The optics simply wouldn’t allow it.

    If the Leafs re-acquired their own 2011 pick for the package Gregor mentions, then the entire deal boils down to:

    To Toronto: Kessel
    To Boston: Seguin, Knight, Versteeg, Kaberle

    Even though both separate transactions might have looked somewhat plausable as individual deals at the time they were made, when you put them together (and every MSM and fan in North America will do just that) and look at them in hindsight, it’s just so lopsided as to be laughable.

    Burkie has to deal with the fact that this one didn’t swing his way. Trying to ‘fix’ it now will only make it worse and could cost him his job.

  • Jason Gregor

    I think Burke only made that deal because he wanted to sign Kessel as an RFA but couldn’t because of the optics, given his ridiculous reaction to Lowe signing Penner, the old cutting off the nose to spite the face.

    While Hemsky and Penner may be better than most 5th overall picks, the simple fact is that they may not be here when it’s finally time for the Oilers to compete. Trading them at their maximum value, whether that value is less than their current abilities (i.e. a 5th overall pick), is a good move, especially since at this time, their skills aren’t helping the Oilers make the playoffs.

  • Jason Gregor

    A lot of bad ideas in this thread.

    Hemsky/Penner is worth more than this pick. This is bad trade straight up. If the Oilers trade one of them to the Bruins Seguin has to be coming back.

    Something like Hemsky + our first round pick for Seguin + their first round pick. That’s the floor of a trade for the Oilers.

    Hemsky + Penner for Schenn is another massive overpay. One of those guys for Schenn is closer to fair value.

  • When did this become an Edmonton Oilers discussion board?

    I for one hope that they trade Penner, Hemsky, Gagner, Paajarvi, and Eberle for Toronto’s 1st and whatever other junk Boston is willing to throw in. Bottom of the heap now, bottom of the heap in the future.

    …love ya Shelbyvillians.

    • Probably since it was posted on All OF THE NATION WEBSITES! Seeing how OUR website seems to have more traffic, & more discussions, you will have to deal with Oiler talk. Because our team has a future….

      • Ogden Brother Jr. - Team Strudwick for coach

        Your team has a future alright… A future of being near the bottom of the league for the next 5 years in the HOPE that they could contend for a stanley cup 6+ years from now…

        Alot of speculation and hope goes into a rebuild, hopefully nothing bad happens in the next five years (injuries or CBA revisementts) that could delay this rebuild another 2+ years… Just ask Atlanta, Florida, Columbus how there rebuilds went.

        Good luck to you on that one…

  • hoil

    I thought George Costanza was with the Yankees?

    Seriously, though, I think the addition of Ryder into the equation cancels out any expectation of a Penner/Hemsky PLUS a significant prospect happening.

    Ryder’s cap hit is roughly equal to Penner/Hemsky, but I believe it is done after this season so the tab for keeping him for only a portion of the season wouldn’t be too limiting.

    While he is paid the same, Ryder’s production isn’t close to what Penner or Hemsky provide. Penner and Hemsky also provide another year of contract at what many consider reasonable to good value.

    Boston gets rid of an unproductive Ryder (+3 for Bruins), gains a productive scorer (27/83)who can handle tough competition and is signed for another season (+7), and gives up one of their two first round draft choices (-6 to -9, depending on Leaf’s finish). I don’t know if a player outside the top 5 is worth losing either of those players.

    As always, it all boils down to what the Penner and/or Hemsky agents are telling the Oilers. If either of them really want to stay and don’t have outrageous demands, why would you give them up unless you are getting a winning deal?

    • Hemmercules

      Ryders numbers are not that far behind Penner and Hemsky’e for this season 14/15/29. Don’t forget it is a contract year for him so his numbers always seem to be better then!
      Ryder would be able to be flipped to a playoff team looking for additional scoring.

      Long term Penner is better for the B’s than Ryder and taking back his salary only to flip him somewhere else is to the Oiler’s benefit.

  • Hemmercules

    @ Gregor

    I always hear Jones as a possible tradeable player in rumors lately. Is there any truth to that?? I really like Jones. He works hard, looks like he’s always having fun and he gets a goal here and there. I’m thinking they can keep him for cheap but sadly I feel like he will simply be let go or traded for a 5th rounder. I realise he’s just bottom end player for this team but they never seem to keep the ones they should. Glencross, Broadziak, Reasoner… Jones next??

  • Quicksilver ballet

    Peter would make a fine politician, we all knew this pick was in play if the Bruins figured they had a shot at glory this season. He’s just driving the price up, looking for a Kings ransom for it i’m sure. Tambellini should sit tight and let Chiarelli come to the Oilers, Edmonton has what Boston desires.

    Penner Brule and Smid for Ryder and that pick… or perhaps even Ryder and Seguin.

    Had to laugh on monday when Sather said Souray is too slow and no longer an asset. Is it at all possible Glen is just peeing in the toilet water so no other GM’s will be interested? Watch for Souray to go on re entries next week, we all know how Glen loves his reclamation projects.

  • Ogden Brother Jr. - Team Strudwick for coach

    Penner, Horcoff, Souray and Hemsky to Burke for Kessel , Phaneuf , Versteeg and TO’s first round pick next year -2012 .

  • Kodiak

    I don’t understand those not wanting to trade Hemsky or Penner. They are only under contract for 1 more year and then gone. If you can’t sign them before the trade deadline, move them.
    In two years when we are starting to be competitive, I would rather have a Dougie Hamilton, Ryan Strome or Ryan Murphy picked up with the TO pick in the system challenging to make the club than the nothing we would have for keeping Hemsky.
    Hemsky is averaging 52 points/season the last 4 1/2 yrs. If his replacement on the roster scores 30 pts, is Hemsky’s extra 22 points worth not having another solid up and coming prospect in the fold? I don’t think so. Thanks for the memories Hemmer. Don’t let the door hit you on the way out!

    • hoil

      I am not a expert on the CBA, but I am fairly certain that you cannot sign a player to a contract extension at this point in their contract (27/83), which kind of mucks up your deadline.

      I don’t think there would be anything prohibiting asking the players their intentions, though. If 27/83 buy into the rebuild you have two real NHL players to work with instead of kids playing with more kids. The Oilers have few enough legitimate players as it is without selling them short.

  • Mouse

    Looks like Burke fleeced Anaheim for Beauchemin. LUpul, a good D prospect and a conditional 4th round pick for Beachemin. That looks like an overpayment. I would have thought Lupul & the pick would have been enough.

  • Rogue


    If the Oil did make a trade for the Leafs draft pick, who is rated in the 5-10 slot among Junior players right now? Is there any one of those that MB may have the hots for, or sees as a steal in that drafting position?

    • Ender

      I’ll let Jason comment on who the Oilers might like, but it’s noteworthy that there are two other centers available around the top 10 besides RNH and Couturier. Ryan Strome is posting good numbers in the OHL and Jonathan Huberdeau is second in overall scoring in the Q. Either could contribute offensively in the Oilers top-6 at some point, although neither of them could be considered big; Strome is currently 6′ 183lb while Huberdeau is a beanpole at 6’1″ 168lb. They both still have awhile to fill out. Brandon Saad is a big LW in the OHL that could be a nice power-forward down the road. At 6’1″ and 208lb currently, he might turn into one of the elusive ‘big guys’ the Oilers have been missing over the past few seasons.

  • Reality Check to the head

    Oilers need only to get rid of Penner. Penner and a propect say: maybe one of our smaller wingers/centres goes. Penner is not coming back to the org when his contract is up. I don’t blame, many have thrown the big man under the bus (including myself) and he will have many suitors once he does enter free agency.

    I hate getting smaller, but what can you do. Harsh reality.

  • 5cups7years

    DO you see a possibility of getting Staal out of pitts? They are deep at center( with makin and crosby healthy that is)Penner and Crosby are both high skilled wingers which pitts has been hurting for years, not to mention they need some scoring to hold onto a playoff position.

    Staal is big, wins f/o can play both sides, and could probabaly score alot more if slotted into a offensive position.

  • stevezie

    This is probably a dumb idea but since they’re en vogue here I’m throwing it out: What about our 1st this year/Penner/Brule for Toronto 1st/Seguin? For argument sake that moves them up five spots this year and gives them a better chance to win now. This only works for the Oilers if we think that Seguin is way better than anything the 2011 top 5 has to offer, which seems to be the case.
    Mock away, I haven’t thought this out.

  • stevezie

    And another thing! I’d say Burke traded something he can spare-a defenceman- to get something he needsan offensive forward. Even if Lupul doesn’t work out this is still not a bad trade because the Leafs had an extra top 4 guy anyway. Good deal for all.

  • Burke should try swapping their pick next year to get their pick this year back. Something like…

    To BOS: Tomas Kaberle, Kris Versteeg, Leafs 2012 1st

    To TOR: Mark Stuart, Blake Wheeler, Leafs 2011 1st