Chicago and Pittsburgh and Edmonton

Photo: Andy/Wikimedia

With the Oilers all but eliminated from the post-season – their fourth consecutive regulation loss dropped their chances to 1-in-40 – and the outcome of this campaign nearly in the books, it seemed a good time to compare the progress of the Oilers’ rebuild to successful ones in Pittsburgh and Chicago

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A lot goes into building a team beyond selecting early in the draft; these are by necessity abbreviated timelines.


  • 2005-06: Finished 14th in the West. Drafted Jonathan Toews
  • 2006-07: Finished 13th in the West, won draft lottery. Selected Patrick Kane.
  • 2007-08: Rookie seasons for Toews and Kane. Chicago finishes in a three-way tie for ninth in the West.
  • 2008-09: Second year of Kane/Toews deals. Chicago goes to the Conference Finals. General manager Dale Tallon demoted.
  • 2009-10: Final year of Kane/Toews entry-level deals. Chicago wins the Stanley Cup.
  • Summer 2010: Entry-level deals of Kane/Toews end; Chicago dumps a bunch of talent and the franchise regresses. Still a power in the West, but has lost in the first round each of the past two seasons.

Thanks to some poor management decisions along the way, new contracts for Kane and Toews triggered a series of trades that saw talent and money sent out of town – significant players like Andrew Ladd, Dustin Byfuglien, Brian Campbell and others would be purged from the roster and it’s taken two years for the team to recover.


  • 2002-03: Finished 14th in the West. Drafted Marc-Andre Fleury 1st overall.
  • 2003-04: First year of Fleury’s entry-level deal. Pittsburgh finishes 15th in the East, drafts Evgeni Malkin second overall.
  • 2004-05: Lockout. A year of Fleury’s entry-level deal burned. Pittsburgh wins lottery, drafts Sidney Crosby first overall.
  • 2005-06: Final year of Fleury’s entry-level deal, Crosby’s starts. Pittsburgh finishes 15th in the East, drafts Jordan Staal. General manager Craig Patrick replaced. Fleury signs a two-year deal with a $1.295 million cap hit.
  • 2006-07: Second year of Crosby’s entry-level deal, first year of Malkin’s, first year of Fleury’s cheap two-year contract. Pittsburgh eliminated in the first round of the playoffs.
  • 2007-08: Final year of Crosby’s entry-level deal and Fleury’s cheap two-year contract. Second year of Malkin’s entry-level deal. Pittsburgh eliminated in the Stanley cup Finals.
  • 2008-09: Pittsburgh wins the Stanley Cup.

Pittsburgh remains a power in the East, though shaky goaltending and defence has been a problem the last two years in first-round exits.


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  • 2009-10: Finished 15th in the West. Drafted Taylor Hall first overall.
  • 2010-11: First year of Hall’s entry-level deal. Oilers finish 15th in the West, draft Ryan Nugent-Hopkins first overall.
  • 2011-12: Second year of Hall’s entry-level deal, first of Nugent-Hopkins’. Oilers finish 14th in the West, draft Nail Yakupov first overall.
  • 2013: Present day. Final year of Hall’s entry-level deal, second of Nugent-Hopkins’, first of Yakupov’s.

Where are the Oilers – in terms of on-ice performance – today? Somewhere shy of Chicago in 2007-08, somewhere north of Pittsburgh in 2005-06? Chicago was two seasons out from the Stanley Cup in 2007-08, Pittsburgh two from a finals appearance.

One thing both Pittsburgh and Chicago had in common was that neither paid big money for their key pieces until they’d had some playoff success – Chicago’s top picks were still on entry-level deals when they won the Cup, Crosby and Malkin were both still on entry-level deals when Pittsburgh went to the Finals and Fleury was on a cheap bridge contract. The Oilers, on the other hand, are about to see Taylor Hall (and Jordan Eberle) graduate to the ranks of paid NHL stars.

Another thing Pittsburgh and Chicago had in common around this time was a change at the top. Craig Patrick, owing to the failures of his team, was dismissed around this time. Dale Tallon, owing less to failures of the team and more to salary problems (including that famous RFA incident), had just a year left in the top job at this point in the Chicago timeline. The safety of the Oilers’ management group is an unknown, though nothing in the team’s on-ice performance should make Kevin Lowe, Steve Tambellini and the rest feel comfortable.

As Pittsburgh shows, a lack of playoff hockey at this point doesn’t necessarily mean that the rebuild has failed or will fail – the Penguins recovered nicely in the years following their miserable 2005-06 campaign. Whether similar progression lies in the Oilers’ future remains to be seen.

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  • GVBlackhawk

    One important item that you overlooked with respect to Chicago’s rebuild was that they were drafting defensemen Keith and Seabrook years before Toews and Kane were drafted. These two, in particular, had time to develop and were good NHL defensemen when the young star forwards entered the league.

    The Oilers moved out their NHL defensemen and replaced them with AHL’ers and Cam Barker. And the Oilers have Barbaro, too. Going into next year, the situation on defense appears sketchy once again.

  • vetinari

    Good article Jonathon for comparison purposes.

    I think that the key is that both Chicago and Pittsburgh replaced their “caretaker” GMs who primarily mined the draft system with GMs who were active players on the trade market and could sell their teams to UFA’s– and I just haven’t seen that in the Lowe/Tambellini dynamic yet.

    In fact, short of enticing one college player, J. Schultz, we’ve lost out on Heatley, Nylander, and almost everyone else who could have helped this team before it reached rock bottom. Either our management team can’t attract quality free agents or make consistent quality trades, or there is some other factor in play (players being averse to the Edmonton market, etc.).

    Management changing coaches every 18 months signals instability to players, and frankly, the solution to send a message that we are ready to win is to change our management team instead.

  • mr_nihilism

    I’m thinking Katz isn’t overly concerned with results. As long as tickets are sold and the beer is flowing, management can #$%^ up all it wants to.

    Management isn’t going to owe up to anything, it’s up to the owner to get out the guillotine. The fact that he hasn’t says it all.

  • DSF

    Since Hall is Crosby in that Pittsburgh scenario, the Oilers should be going to the cup finals this season.

    Of course Pittsburgh also had Marian Hossa and Sergei Gonchar in his prime on the roster.

    So not only are the Oilers missing players of that calibre but they also don’t have a Malkin or Jordan Staal.

    Considering how often they’ve drafted in the top 10 over the past few years, that’s pathetic.


    Crosby is listed at an $8.7M cap hit that year. Pittsburgh still won the Cup with a middling overall cap #, but with Crosby at $8.7M, and all of Whitney, Guerin, Gonchar, Satan, Kunitz, Orpik, Fleury, and even Malkin’s cap hits at >$3.5M, many of their players were getting paid real dollars. Malkin remains a bargain at his rookie max cap hit and there are a handful of useful players making


    Crosby is listed at an $8.7M cap hit that year. Pittsburgh still won the Cup with a middling overall cap #, but with Crosby at $8.7M, and all of Whitney, Guerin, Gonchar, Satan, Kunitz, Orpik, Fleury, and even Malkin’s cap hits at >$3.5M, many of their players were getting paid real dollars. Malkin remains a bargain at his rookie max cap hit and there are a handful of useful players making

  • Ogie Oilthorpe

    Good article, puts the rebuild in a little better perspective. I know the D situation is unstable at best, but I think with Klefbom coming over next year, and one free agent signing or trade in the offseason that can be taken care of to a decent degree. Not a contender next year, but at least a play-off berth to give the fans some hope.

    Offensively, I won’t re-hash what everyone seems to agree on. But management has to change. That seems to be a theme with the aforementioned teams as well, and frankly ours doesn’t have the sack to make the moves needed to complete the rebuild.

  • Death Metal Nightmare

    i love the “look at these two teams that won cups. when is Edmonton getting theirs?” model of analysis.

    its bad.

    this team has its own highly unique problems, and highly unique player makeup / roster.

    go over teams that were awesome that never won. Ottawa through the early 2000s with Chara, Redden, Hossa, Havlat, Alfredsson, Bonk, etc?

    how about TBL once Stamkos/Hedman arrived?

    Sidney Crosby put up 102 and 120 points his first two years. Hall looked like that player for about 5 games. the rest of the team can barely execute a breakout or get out of the zone fast enough. most of the team looks like they fit better on inline hockey teams where over passing and fancy garbage works.

    id be worried.

  • Why doesn’t someone write a fire the management blog. These tiptoe articals is all we get. We need to be fired up.

    I look at New York this season and feel envy. They are competing and they have 3 top fight prospects sitting in the minors or junior in Strome, Reinhardt, Neidereider. The abondoned this overpriced mentorship program and letting the horses run, sink or swim. Right now their swimming and their future looks pretty good. If Snow and Wanger perenial abomination makes the playoff, I’m going to eat some crow.and dust off the Captain Highliner Jersey.

  • outdoorzguy

    I think the Chicago 2003-04 season should be included, because they finished with 59pts and it was the 5th time they missed the playoffs in 6 years. A much more painful rebuild than the Oilers.

  • outdoorzguy

    It truly appears as though whoever is managing this team in a year or two will have to do a major overhaul on the rebuild. Bottom six, blueline etc. But the biggest problem is that you can’t fix scared. Save for a few guys, this is a group of p*ssies. Flat out. No intestinal fortitude whatsover. Explains the generally non competitive nature of the club.

    Good luck fixing that problem new gm.

  • Eddie Shore

    2 key moments in the season:

    1) the triple C injury just prior to the 9 game road trip – no help delivered by mgmt.

    2) 5 game win streak prior to deadline: St.L, steal by Khabby, close win after being outshot by CBJ, caught Van. napping and then 2W against an awful Flames team to get team back into the playoff race. – mgmt. delivers Smithson for a 4th, receives not a single asset for any of its UFA instead continues to ignore deficiencies and team is unable to beat a Phoenix squad that traded away Torres and Lombardi.

    Enough games have been played to confirm that the players and coaches have exacted every point they can based on their ability. The failure to reach the playoffs, again, rests squarely at the feet of mgmt. and ultimately ownership. The team needs are the same ones that existed in April 2012.

    This has been a wasted year.

  • Clyde Frog

    Yeah Hall and Eberle’s EL contracts are up. But there isn’t much of a team beyond them, and I think that’s the key. Hall and Eberle, while being key peices to build around, but unfortunately they’re not the ones that are going to win the cup. They might score all the goals and get the cup winning goal…but it’s going to be the rest of the team that wins it…ie: the Oilers are doing this a bit backwards where they get an elite core and now they need to get the appropriate filler around them, where Chicago already had Keith/Seabrook, and the rest of the team was growing up already together – ie: Kane and Toews were the stars that elevated the team to the next level. Hall and Eberle raised this team to the next level, that level being a step up from teh very bottom of the league. What’s the rest of the team got to say for itself? Hopefully Yakupov’s contract will just be coming up when we win a cup, that’s the only way I see this as a comparable year. Unless we win the draft lotto and Jones’ contract is the one we can wait for…ugh.

  • A-Mc

    I’m not ready to fire management yet. Over the last 2-3 seasons, their mandate has been to draft some guys and develop them. No where in that process is there room for attempting block buster trades to bring in good guys to surround the young hot shots; and unfortunately, even if they wanted a block buster trade, they didn’t have any pieces to make a deal!

    As others have said, the oilers are essentially an AHL team with a few Vets on their way out and 3-4 top end NHL players. When it comes to making trades to fill holes, No one wants the old farts that cannot skate and you can’t flip AHL’ers into Keith Yandle’s. The only pieces of value that this team has are the pieces we need to keep for ourselves.

    So what does this mean? We’re still stuck bringing in talent via draft (ie: Waiting). Quality UFA’s wont sign here because we’re not winning a cup anytime soon. Rental Pending UFA’s are an option you explore when you’re already a contender; otherwise the consequence of repeated rentals is that you sell out your future. And as previously statd, hockey trades aren’t going to flip Linus Omark for Sidney Crosby.

    Given the circumstances, i dont think there is much choice for management but to build and acquire pieces slowly and bank on the fact that your core is developing into a well rounded bunch of young chaps that might get you close to the playoffs. At some point you’ll have enough newly drafted talent outside of the core that are trad bait for a brand name guy. Once the Oilers get to that point, then we’ll see some changes.

  • This question is in no way a defense of where the Oilers currently sit in their development but; does it make a difference that neither Chicago nor Pittsburgh (Chicago more so) were intentionally rebuilding during their suckiest years?

    In my opinion when discussing timelines that puts the Oilers well behind either of those two teams.

  • Dangerous Neil

    Even though the Oilers have missed the playoffs for seven straight years, for the first three of those we were legitimately trying to make the playoffs (see the Souray or Penner signings). The rebuild is only 4 years old. At that point the Penguins had yet to make the playoffs, with the two best players in the world on their team. It is tough to preach patience after so many years with little to cheer for, but anyone who expected this rebuild to be finished and the Oilers to be contenders in less than 5 years was dreaming. We are still a couple of seasons away from being able to call the rebuild a success or failure.

  • Randaman

    Enough with these comparisons that only serve to keep you in the good books with Oilers management (if you can call it that). Call a spade a spade when appropriate and now is the time. Tambi has failed miserably finding pieces to compliment the extreme talent and speed in our top 6. He has drafted poorly beyond the first round. Lowe, who everybody knows is actually pulling the strings should also be down the road. He should have been gone years ago. There, I feel better…

  • Knowing the short sighted fickle nature of posters on this blog, myself included, I am still going to hold off judgement until next year. As stated, Chicago and even Pittsburgh already had some key pieces before they started the rebuild. Who are our key pieces? Hemsky? Horcoff?

    The Oilers rebuild model truly was to blow it all up, ship practically the entire old team out and start over.

    I am hoping we have drafted the talent to build around, and this summer the actual building can begin. I think we all know what needs to happen, so now we will see if our management is capable of going out and getting a top 2 D, a bigger two way 2nd line centre, a good sized LW, and a retool of our bottom six.

      • Dangerous Neil

        I suppose I would ask who had trade value last year? Hemsky was not high on the value list, and Gagner would have left a big hole at centre.

        Dubnyk was in my mind as well, and though I really like Smid and Petry, I don’t think they are in the same area as Keith and Seebrook.

        How did Chicago get Sharp? Was that another draft choice as well?

        It could be that Magnus and Harti and Klefbomb work out and become our “key pieces”, but who’s to say right now.

        I suppose what I’m getting at is I think we had a different situation in Edmonton that required a different approach. It would be hard to look at our forward talent and say we didn’t accomplish anything.

        Like I said, I think we have something incredibly special to build around, we even have enough players that could be traded to build around the talent in town, but it remains to be seen whether or not we’ll do that. I could see them drafting a decent centre with some size and skill, then saying, once this player develops, we’ll have it. I mean, have any of the above mentioned rebuilds hinged so much on so many players developing?

        Dubnyk, Hall, Ebs, Nuge, Yak, J Schultz, Gagner… and to a lesser extent, Klefbomb, Harti, Magnus, Lander, maybe even another D prospect ? That seems like a lot.

        • DSF

          By the time your suggested approach could work out, all of Hall, Eberle, Hopkins, Yakupov and Schultz will have burned through their ELC’s and the Oilers won’t be able to keep them all.

          As JW points out in his article, the key to being able to win is to do it with important pieces on affordable contracts otherwise you don’t have the cap room to add the other pieces you need to win a cup.

          • DSF

            I’m not really proposing anything, just answering two of Willis’ comments and questions about one of my earlier posts.

            I understand one of the main points in getting to the cup during a rebuild is to have your emerging stars still in their ELC, that way you can buy some more expensive players to help make the run. I agree with that. Having Hall and Ebs off their ELC is not so bad considering the rest of the salary we have coming off next year, and hopefully a buy out or two.

            I think the trouble is going to be having all the wunderkids off their entry level deals. But maybe by then they will be so dominant it won’t really matter. I mean, just look at the Burgh, or Chicago. All those guys are off their ELC and they are still powerhouses in the league.

            More than any other Whitney’s injury hurt this team so much. If he was in top 2 form, everyone else on our depth chart would have been pushed down one. Whose to say if we would have gotten the pieces we have now, but still getting a top 2 guy this summer is going to be really hard.

            I still say see what it takes to get Coutier and Yandle. Combine that with a Klefbomb, and one year older Shultz, Yak, Hall, Ebs, and Nuge, and maybe that’s enough.

            I would think our fourth line is what any fourth line should be (can win a draw, has some energy players that can play a little hockey, and maybe even contribute every once in a blue moon). Our third line is a real mess though. I really don’t know, it’s all just speculation which is really fun to discuss, but not very productive I guess.

  • Pitts, and Chicg., are used to draw comparisons to the Oilers, because of the draft positions these teams were afforded.

    These teams won he cup because the support staff was overhwhelming and players like Guerin, Hossa, Ladd, Campbell, Buffylgen,Sharp. Chicago already had three studs on the backend.

    In todays market its alot more difficult to shore up your roster’ The Oilers need two No. 1 pairing D men, a backup goalie, a stud Center man, and complete thrid and fourth lines, for the most part. You cannot assemble that in one , even two summers. Tambellini did nothing in the last two yeas to start that process, thats why they are in deep doo doo.

  • In an abbreviated season like this one, there has been little time for practicing between games. I believe this is critical when you have a new coach with a new system and young players, along with new additions, including rookies, as talented as they are. Did I read somewhere that individual coaching has been provided to players through the use of video? That would likely have been done on the airplane a lot of the time. But what about practicing team play? Krueger had optional skates, allowing players to rest between games, and I agree with that. But had this been a regular season, with time for the players to rest, reflect and practice between games, could the result have been different?

  • Quicksilver ballet

    I’m almost afraid to find out what managements agenda is for next yr. Is it going to be Blind Eye management yet again, or are they finally going to make an effort to give the fans their moneys worth.

    It’s inappropriate to compare whats happened in Edmonton to Chicago or Pittsburgh. With Taylor Hall locking in his income for the next 7 yrs. I’m starting to wonder if he’s frustrated to the point where he may want to earn most of that wearing a different jersey. That would add some discomfort to the chairs management are seated in.

  • Oilfred

    I don’t buy these comparisons at all. They both had superior assets when you the process began IMO.

    As for it taking Chicago taking two years to recover they have been a very good team that came within a whisker beating the Vancouver team that very nearly won the cup.

  • DSF

    You know what analysis I would like to see? A breakdown of the non-draft personel moves (Trades, UFA’s) that the rebuilding teams made in during their rebuilds. Compare PIT, CHI, CBJ, NYI, ATL and EDM. It is obvious that you cannot build through the draft alone, but I want to see the other moves these teams made and what leads to success of failure.