The Edmonton Oilers and the window to win

The last few days have seen an explosion of trade rumours (as well as some actual moves) and the expectation is that the Edmonton Oilers will be very busy over the next two weeks. Once again, they enter the NHL Entry Draft with a first overall pick, and once again the next two weeks project as critical in the long-term future of the franchise.

On thing that Steve Tambellini and the rest of the Oilers’ brain-trust should keep in mind throughout this period is the Oilers’ window to win.

Two trades stand out to me over the last few years, trades where the Oilers got really good value but still didn’t clearly win the day. We talked about the Chris Pronger trade late last month, and the collection of assets the Oilers walked away from that deal with was impressive. In terms of value, the Oilers got a lot of it from the Ducks. The Dustin Penner trade is a similar story, though to a lesser extent.

When Steve Tambellini dealt Dustin Penner at the 2011 trade deadline, he got fair value in return. He got the first round pick that turned into Oscar Klefbom, defenseive prospect Colten Teubert, as well as the third round pick in this year’s draft (note: that third-round pick would have been a second-round selection had the Kings won the Stanley Cup in 2011, but because they won in 2012 it remains a third rounder).

That’s a fair package in exchange for Penner, in terms of value. The only problem with a deal like that is what it means for a team’s window to win – the package Edmonton received had no major impact in 2010-11, no major impact in 2011-12 (Teubert played some games in the NHL but was clearly overmatched) and is unlikely to have a major impact in 2012-13. So, the value will eventually be good but the immediate impact is minimal.

That’s why rebuilding teams make those sorts of trades: pain now in exchange for benefit later.

As a team exits the teardown phase of a conventional NHL rebuild, that’s a harder trade to make, for a few reasons. The first is that the rebuilding club is now trying to take strides forward – a team that perpetually trades assets now for assets later never gets anywhere, and all rebuilds need to have a timeframe for transitioning from a terrible team to a competitive team.

The second reason is that the assets accumulated at the start of the rebuilding window start getting a) expensive and b) antsy for wins. The Oilers have one more season in which Jordan Eberle and Taylor Hall will be in their entry-level deals. The year after that, Ryan Nugent-Hopkins will be on his second contract. A team doesn’t need their best players to be on entry-level deals, but it makes it easier to put a winner together – Chicago, for example, won five playoff series in the last two years of Kane and Toews’ entry-level deals. They haven’t won a playoff series since those players started getting paid full value, in no small part because they have had to jettison strong supporting pieces like Dustin Byfuglien, Andrew Ladd, Brian Campbell and Antti Niemi.

The Oilers have a short period of time to make the jump from rebuilding to being competitive. At this point it seems likely that they won’t make the playoffs during the Hall and Eberle entry-level contracts; they need to improve greatly to manage a playoff appearance during the Nugent-Hopkins deal.

It is of course worth remembering that these sorts of teams can rise in a hurry if things are done right – Chicago went from missing the playoffs in 2007-08 to losing in the conference finals in 2008-09 to winning it all in 2009-10; Pittsburgh went from 58 points in 2005-06 to 105 points in 2006-07 to the Finals in 2007-08 to a Cup win in 2008-09. The talent available at the top of the draft can trigger a rapid and dramatic turnaround.

To manage such a turnaround, however, teams need to stop tearing down and start building up.

A case in point is the current Sam Gagner rumour making the rounds. According to the rumour, the Carolina Hurricanes would trade Edmonton the eighth overall pick straight across for Gagner.

That eighth overall pick is a valuable piece; a piece I would argue represents fair value for Gagner. Additionally, it would allow the Oilers to pick Nail Yakupov at the top of the draft and supplement him with either a strong centre (perhaps Mikahial Grigorenko) or to land one of the draft’s top defenders – not Ryan Murray, but a Reinhart or a Dumba or a Rielly or a Trouba. The appeal to that deal is obvious.

The problem is what it does to the Oilers’ window to win. For all the criticism he gets, right now Sam Gagner is a very useful centre of a secondary scoring line. He contributes at a high level in the NHL right now – and his two-way game has improved leaps and bounds since he entered the league after being the sixth overall selection the summer before. If Grigorenko were to fall to eighth and the Oilers made that trade, maybe the impact isn’t that bad, but if the Oilers opt to address their defense how long is it until that defender contributes?

The point is that somewhere along the line, the Oilers have to shift their primary focus from the future to the present. I’d argue the time to do that is now.

This week by Jonathan Willis

  • Quicksilver ballet

    If Trouba is around at 8- I’m making that deal every day of the week. This Oil has to many smallish similar forward group. Sorry Gagner is a great kid but picking his seat off the ice way to many times, if this team wants to get serious about being a real hockey team we need to get bigger and tougher.
    Jacob Trouba would add some grit to our D size and decent puck moving ability.

  • DSF

    Keep Yakupov to play on his right or left side, hemsky at the other wing and we have two high flying beautiful scoring lines..
    Gags and Yak would be perfectly complimented by a hemmer.

  • Come Join The Park Parade:

    We all know we can’t win with Gagner?

    I disagree with that, and I have been pushing for them to draft bigger grittier players for years. If he has 2 small soft wingers then I would tend to agree. If he was between Hall and Yak who both play bigger than they are, I think he would be fine and see him eclipsing 60 points.

    If Galchenyuk is available I do this trade today. If Grigorenko is available I would probably still do it if after the interview I believed the reason for his falloff was the injury and mono. I do not trade Gagner unless it nets me a bigger centre that I feel has more potential and can play 2nd line centre next in the next 2 years and be as effective or more effective at that time.

    The hole we would have using Horcoff as our 2nd line centre is much bigger than our holes at D.

  • Quicksilver ballet

    @ Cody

    Can’t win with Gagner as a second line center Cody. If the Oilers 1st and 2nd line centers are out of this world, then, maybe they could carry Sam most nights. Can’t win with him as a second liner though. There’s plenty left, still better than Gags if both Grigs or Galy are gone by that 8 spot. There are 3 tough decisions to make. One at a time in the next 12 months, they’ll all be dealt with.(10,83,89)

  • oilers2k12: If Hemsky is on Gagner line then I would tend to agree that line is too small and soft to play against.

    I would be looking to move Hemmer at the very first opportunity.

    Yak and Eberle are obviously ahead of him on the depth chart and the last thing we need is a soft, skilled player who has been accused of trying to do too much, playing with no scoring support on the 3rd line and making 5 million a year.

    If you move him to the left as suggested then one of the 2 lines is super soft. No way you would want him Nuge and Eberle on the ice together.

    Package Hemsky plus magic beans to get the best Dman you can get, or the highest draft pick you can get.

  • @ Come join the Dark parade:

    So you see gags as a 3rd line centre? In that role I see him Failing the same way Pajjarvi did. He is a smaller skilled player that needs to play with other skilled players to be successful.

    • DSF

      I think Hopkins is a fine player but, if the Oilers had drafted differently in previous years, they wouldn’t find themselves in the pickle they are now.

      Imagine having the first overall pick 3 years in a row and being almost forced to take another winger (the easiest players to find in free agency or in trade).

      Let me tell you a story.

      Last summer I was in Osoyoos and happened to walk into a bar and started chatting with the guy next to me. Total serendipity.

      As it turns out, he happened to be the former GM of the Kitchener Rangers and the former head scout for Hockey Canada.

      We discussed virtually every Oiler player and the draft which was coming up in a few days.

      He was very, very familiar with Sam Gagner who he characterized as a very entitled player who would walk into the coaches office and demand more PP time.

      We discussed Gilbert, Petry and Chorney and he was adamant at that no winning team would have ANY of them on the roster because they are too soft.

      We discussed the upcoming draft and he was adamant that, when all is said and done, Huberdeau will be the best player in that draft because of his big game ability and competitiveness. He did say Huberdeau likely needed more time to develop but that he will be the best player in that draft.

      In discussing Paajarvi, he actually laughed out loud and suggested the Oilers blew it big time taking him at 10th overall.

      Take from it what you will but the guy knows hockey and believes the Oilers don’t have a clue what they’re doing.

      The results would seem to indicate he may be on to something.

      • Quicksilver ballet

        As I was about to dismiss this as typical DSF self aggrandizing and self promoting claptrap, filled, as always, with idle speculation stated as bald fact (“Huberdeau will be the best player in that draft”), drive- by smears( gossip about Gagner demanding more pp time 6 years ago in London?) and recycled hindsight(yes, we all know about your MPS-Kulikov hobbyhorse…enough, already!), I did notice something that made me think there might be tiny kernel of truth in this tale. DSF and his mythical friend said the Oilers would never be a winning team with Gilbert, Chorney and Petry on their roster, and in the same breath, that the Oilers don’t have a clue what they are doing. Yet, DSF, Gilbert has been traded for a steadier hand on the tiller in Schultz, Chorney is buried in the minors, leaving only Petry, who has made significant strides since that momentous conversation in the bar in Osoyoos last summer, as the surviving member of that trio. Amazing! DSF actually complimenting Oiler brass for getting something right.

      • Wax Man Riley

        Cool story bro….

        …actually though…

        It’s kinda cool. Was it Steve Spott?

        Thing is, that is one hockey mind. Craig Button sees Grigorenko being chosen a #20. I am not the hockey mind Button is, and I can tell you he will be picked well ahead of 20.

        Just another hockey mind.

        Not that I think Tambo knows what he is doing, mind you. I have some faith in K-Lowe, since he has proven he can build a winner, but after the ’06 exodus, it feels like they put Tambo in that position in order to fail and get some high draft picks. Do an actual rebuild.

  • You dont trade a #6 first rounder with 5 years of NHL experience, scoring a steady 45-50 points and is only 22 yrs of age.. for a # 8 first rounder .Let me assure you that Gregerenko and Gaylenchuk will not be there at No. 8.Yes Gagner has his faults, and he might be what you see., but at least you can see it. If you move Gagner,[ Pkg.] it should be for someone like Staal.Gagner biggest fault is that he has learned to play a tough game.. and his face offs are week… he gets thrown out more often then he faces off.

  • Quicksilver ballet

    @ Blacque Jacque [Oh, that guy? Yeah, my eyes seem to automatically glaze over when I see his name by posts. Such an unbelievable font of negativity.]

    If you feel there’s anything positive about 30th,30th and 29th place finishes, please pass whatever it is you’re smoking around and share. Is it really negative, or perhaps a little closer to reality?

  • Quicksilver ballet


    I don’t disagree with you, their drafting has been horrendous for the last 20 years. And 2009 may go down as one of their worst drafts of all time, which is a major reason as to why there is no support structure behind the #1’s.

    I’m just saying, RNH possesses characteristics that could have him winning scoring titles and in your little hypothetical, you only have them drafting ONE center. You seem to know your hockey, I don’t know how you missed that…

    So maybe instead a guy could say Voracek, Eberle, Kulikov, Seguin, RNH, Yakupov.

    In: Voracek, Kulikov, Seguin
    Out: Gagner, Paajarvi, Hall

    I make that trade.

  • Spydyr

    Gotta have all your ducks facing the same direction before you can put your ducks in a row. This was the vortex the franchise was in post-2006. They were trying to get back to the Stanley Cup Finals, yet, they kept dealing their players for futures. Chris Pronger for Lupul, Smid and a pair of 1sts. Ryan Smyth for Nilsson, O’Marra and a 1st, etc, etc. Smid is paying dividends now as is Eberle. But that’s 5 years later. The time in between was a struggle and I’m not interested in seeing this team do that again any time soon. Dealing a current roster player for a pick…maybe it would be a good trade for 3-5 years down the road, but it won’t help the Oilers make the playoffs next year. Now, if TSN got you excited with swapping 1st round picks with Montreal with PK Subban coming here, that’s a trade you could make. If you have to move a roster player out, that’s fine because you’re bringing one back and addressing need with PK Subban.

  • Spydyr

    While I’m on the PK Subban thread…I love his talent and it’s exactly what the Oilers lack on their blue line. But he continues to have issues with positioning. Not the best student of the game, has more of a tendency to wander. I could also see him being a polarizing figure in the dressing room. Think Dion Phaneuf here.

    I like the character in the Oilers dressing room. I think the leadership will transition to Hall and the youngs guys very soon. I’m not sure what adding PK to this lockerroom would do to that.

  • Bucknuck

    Perfect analysis…the focus has changed now that we’ve drafted #1 three times.
    The focus is filling in the team with the missing pieces and moving into contention!