When discussing the future of the
Oilers I am often confronted with the idea that the team should hold back on making big moves or mortgaging the future until their “Window to Win” opens. That
sounds very conservative. That sounds very safe. To me, it also sounds very

I have always been astounded by the sheer volume of people
who believe a window to win will magically appear for the Oilers, as if perhaps
the hockey gods will decide that now is their turn. It has not been my
experience in life, sporting or otherwise, that good things come to those who
wait. It’s a nice thing we tell kids so they can be quiet, but in practice they
are terrible words to live by.

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The last six seasons of Oiler hockey have been predicated on
the belief that if you are terrible long enough that eventually you will be
good. They drafted first overall three years in a row (!) and nothing got
better. They sat back, providing about as much care to the roster as I do my
lawn, and waited for the magic to happen.

“No guys, for real. It’s happening soon!”

We waited. Oh, we waited. And waited. The club played a
little shell game with “when the rebuild started” that confused the issue but
they’ve been rebuilding since the 2009-2010 season. The rebuild has now totaled
six NHL seasons. Still, that damned window has not yet opened.

barred window

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Sometimes it felt like we were at a fancy art show and
everybody was staring at a bunch of squiggly crap exclaiming how it amazing and
evocative it is and we just nodded our heads in agreement despite thinking
everything in the gallery was complete garbage. The Oilers were a terrible team
but still we all agreed they had to win eventually.

I think even the players bought into the idea that pretty
quick they would be a good team by virtue of destiny alone for a while. It hasn’t
worked out so well. I should mention that I don’t think anybody on the Oilers
believes they will be good without massive changes or upgrades now. Those
lessons have (or should have) already been learned.

The Edmonton Oilers’ window to win is not something that
will come on its own.

They did not take a number like at the deli of a Sobey’s and
are waiting their turn.

There will not be a window to win unless they make one.

That is why it is imperative that they stop wasting years of
service from players in the primes of their careers. All three of their
previous first overall picks are now finished their ELCs. They already
blew the opportunity to win while they were cheap.

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Some random numbers granted Edmonton the best young player
in a decade. The team can’t afford to get caught up in the delusion that “their
window” is actually a real thing that they have absolutely no control over and
that exists in a mythical future.

The fact is that nobody is going to give Edmonton anything
they won’t take for themselves.

Everybody knows what the Oilers need.

They need a Goalie and at least one legitimate big minutes defenseman,
probably two.

It makes no sense to hold back and not go after these pieces
for the sake of an imaginary window of opportunity that hasn’t imaginarily
opened. There is no opportunity to win without these players on the roster.

Goddess Fortuna

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Safe is death and fortune favours the bold.

If the Oilers trade every single pick in the 2015 draft that
comes after Connor McDavid then I will be elated so long as the club finds at
least one goaltender with a reasonable chance of being their starter and a
legitimate 20+ minute a night defenseman.

Could that be Cam Talbot and Brent Seabrook? That sounds
like a pretty good “Best Case Scenario” to me but it could be countless other
combinations of an up and coming netminder and blueliner on a cap-strapped team.

If we can all agree that the Oilers need those things (two
defenders and a goalie) to win, then what
is going to happen over the course of this coming year or the following that
will change their needs?

The answer is nothing. There is nothing that waiting any
longer will do to fix the holes on the roster.

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There was a time when the Oilers had no high end talent at
all. None. That’s how this rebuild started. They had to just lose and be
patient until the draft provided them what they needed. Now they have several
forwards that could not have been acquired by any other means. But, they have
transitioned from having nothing of value in general to nothing of value in
very specific positions.

The Oilers do not have two impact right-shooting defensemen in
the system that just need time. They do not have a goaltender who looks like he
might be ready to take over as the starter. There is simply nothing immediately
wrong with the Oilers that time will assuredly take care of.

If waiting around isn’t the answer then that surely means
the time to act is now. The window to win is a nice delusion but there’s
nothing behind it except blind faith that the hockey gods will make the Oilers
better. I don’t think Peter Chiarelli should sit around and wait for more than
what the hockey gods have already provided. It starts with current and future draft picks and moves up from there in order of willingness to move. 

The real truth here is that window for waiting around is closed. Now is the time to act.

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  • Word to the Bird

    Completely agree! Good read!

    Now I wanna play a game. It’s called “would you trade McDavid for…”

    Would you trade McDavid for… Seth Jones, Aaron Ekblad, and Vaselivsky?

    • RandomScrub

      I’d consider trading the #1 (McDavid) to New Jersey for Schneider, Larsson, Severson, and their first rounder (#6). Flip the #6 plus whatever other picks needed to Boston for Dougie Hamilton and sign him.

      There you go, a proven but not too-too-old starting goaltender, and three young high-end potential defenders, at least one of which is already proven. Overpay for a short term UFA veteran defenseman (more cash, but only 2 or 3 year term) if you feel you need a bit more. Cup within 3 years? Eh? Ehh? 🙂

      • sportsjunkie007

        Not bad at all!

        Klefbom – Larsson
        Nurse – Hamilton


        Looks solid to me. Wonder what else boston would need for Hamilton. #6, 16 and I think jersey would have to give us there 1st next year and we could add that to the Hamilton deal. Ahh pipe dreams, they’re fun.

      • sportsjunkie007

        Lets get the leaf fans excited… How about McDavid to toronto for Morgan Reilly, pick #5, #24, Nylander and Bernier. Depending upon wether Boston would trade Hamilton for picks #5, #16 and 24.

        Klefbom – Hamilton

        Nurse – Reilly


        So basically McDavid for Hamilton, Reilly, Nylander and bernier. I don’t like it sorry leaf fans haha

  • Can’t disagree more! Edmonton needs to be cautious as in 3 years when Mcdavids contract is due he will need to be signed long term or match RFA offers! At that point other members of the core will have contracts that will be coming due, core will have to be traded to stay within cap! You will need up & coming draft picks or you will be modelling the present Penguins with no depth and traded away draft picks.

      • Cheap Shot Charlie

        In 3 years oilers won’t be at the point of winning the cup! Mcdavid will have to be signed before he becomes a RFA what will he be worth? Toews & Kane are both going to $10.5 each what will a generational talent (Mcdavids) be worth in 3 years? You will have to trade probably 2 members of the core to keep Mcjesus for probably future potential & draft picks in 3 years you better have some of this years draft ready to step in, it is a deep draft. Oilers will need many players on entry level deals as the cap situation only allows few star or core players of elite talent/team. They need to draft well & develop!

        • RandomScrub

          NOBODY successfully trades there way from being a loser to champion in cap era. Draft well, devevelop well, make it into to top half then trade and sign free agents if needed to take the last steps to win cup.

        • STR8 SHOOTER

          I have my doubts McDavid will get a 10+ million/ right of his ELC like you are stating. Toews and Kane got those contracts because they brought 2 cups to Chicago. They had a 5 year 6.3/ before. Crosby got a 5 year 8.7/ after his ELC. And Stamkos got 5 years 7.5/.

          • justDOit

            Mcdavid will be making $3.6 million this year in 3 years if he is the best player in the league he will be expected to paid as such at that time when Draisatle, Nurse Yakapov, Hall Eberle & Nugent-Hopkins plus the players you are trading all of your draft picks (for impact players) contracts are all due. Mcdavid if not signed will be worth whatever he wants! Burke as GM in Calgary would love to do it! Oilers would receive 5 first round draft picks. Draft wisely, develop and make shrewd trades. Oilers need to be conscious of there future as they will be capped out!

      • Cheap Shot Charlie

        I agree with Keeps on this one all the way. PC needs a season to settle in before he does anything huge. He needs the time to familiarize himself with the organization. I think rushing in to a new job and immediately being rushed because your ‘window’ is closing could be more disastrous than showing at least one season of patience.

  • Retsinnab5

    McWindows -McDavid ! Well i’m all in for opening those windows now . Like it or not , McDavid is that window , whether we trade him now or in 1-3 years from now if he proves his worth . Keeping him long term will be difficult . His current worth could make us an immediate contender no doubt for years to come I suspect , and fill all our holes with good talent . Trading him would leave us with all our other young talents basically intact with a fine core to compliment them and fit in to long term cap I would expect . Keeping McDavid is also a window of opportunity , so it’s a win win situation for Oiler fans .

  • sportsjunkie007

    The Oilers have a ticking time bomb that’s about to join the payroll, it’s name is Connor McDavid. We’ll get 3 years of his entry level contract, then he’s going to start to get very expensive. We need to find a way to start winning very soon, before the salary cap starts to rip apart our team.

  • Butters

    There is no way any team could afford 4 #1 overall a 3rd and 7th overall pick. Most team have 3 super elite players on their roster. Look at LA, Chicago and Pittsburgh. These teams have major problems and will all be in trouble this summer.

  • Word to the Bird

    The Oilers should do what the Cavs did once they got Lebron back, which is maximize their window now. Forget the future, Edmonton has youth in spades; they can afford to give up a little bit. Its time to load up and make a push

  • PEBOisONit

    Could Nurse and Klefbom be our Keith and Seabrook?
    Could McDavid be our Toews?
    Could (insert Hall, Eberle, Nuge, or Yak) be our Kane?

    The window is open, it’s just a matter of whether or not we wait too long to take any action before it closes. Nobody is untouchable except for McDavid.

  • BabyNugeMonitor

    Good thing you are not the GM, Mr. Henderson, because your willingness to trade an entire draft class sans #1 overall is lunacy.

    Concur with the premise of this article: that waiting for an opportunity will guarantee it never arrives. And that Edmonton should force the issue via trade to make their own luck. That said, the modus proposed is inherently flawed.

    Moving #16, #33, and #57 for immediate help is unwise. If ever there was a time to acquire quality on the cheap, it is this draft class. Paying a premium for a 30 y/o defenseman with 1 year term, who wants a new deal for 6-8 years (Seabrook) will absolutely handicap this burgeoning roster at the very time it cannot afford to have a lodestone tarried around its neck.

    Smart teams pay their own drafted & developed players to engender loyalty and reward performance. Paying free agents to fulfill prime roles has not worked, and will continue to be a fool’s errand. As a business model, paying for past performance is unsustainable and that is precisely what is rewarded with free agent contracts. Especially for players on the wrong side of 29. It is a young man’s game – don’t pay for the performance of someone who will only get worse.

    Sekera & Frandson. Combined, we could pay them as much as it would cost to sign Seabrook. Added bonus is the opportunity cost is only dollars – not assets. Chiarelli will get this right.

      • Cheap Shot Charlie

        Really? And that’s why they had to gamble on Vanek and Pominville? Dubnyk is the actual reason they even made the playoffs this year. I’d say Parise and Suter are NOT doing the trick for Minny.

      • BabyNugeMonitor

        Really? Best Parise has achieved since signing in MN is 62 points and the Wild have advanced out of the 1st round of playoffs twice.

        Suter’s influence is much greater as a 1D, but it’s a team sport and those two guys cannot win the cup without significant help.

        Exclude the performance factor (clearly an impossible separation) and for $98MM (each) their contracts run until 2025 when they are 39 years old. Parise is a liability in 3 years, if not sooner.

        The upside for both signings was the opportunity cost did not involve moving assets to acquire each player (outside of $ and cap space).

    • Dirtski

      Bump to this because it’s a good idea. Thanks Butters – now back to your room your supposed to be grounded.

      I agree, no more slow play. Though the eventual cap-hell we’ll face is a reality. Currently the core of hall-ebs-nuge are great contracts – kudo’s to past GM’s for securing that. Not to mention Lander and Yak – though for the sake of Yak the man and good hockey itself I sure do hope his value goes up – even if it means a tougher cap crunch in a few years.

      A great article if I could request would be a breakdown of the timelines of what our cap is expected to be with the additions of Nurse and Drai after their entry levels run out and a Mc D’ projection, along with the time remaining on the trios contracts – those 6 players alone…say with Ebs/Nuge/Hall making say… 8mill each after these contracts, Mc’d at 10, Nurse at 8, and Drai at 8 = north of 50 Million on 6 players! Even if the cap is at say 80mill at that point that leaves 30mill to fill a whole roster. I mean, who knows what will happen (besides a cup – that’s gotta be a coming) with all this young talent. All I know is….WOW…what a great problem to have if you really stop and think about it.

      • Retsinnab5

        That is why the Oilers need to trade one of the Nuge, Eberle, Yak for a top defenseman like Burns..

        Get on with it and start building a team and not a bunch of fancy forwards.

        You cant keep all the top forwards anyway


    Strike while the iron is hot.

    McDavid is BLESSing behold

    so excited for June 26. new lease on life as fan too

    be bold. get Seabrook and some heavy player PC

  • Kevwan

    Good things happen to those that wait, and we must wait one more year. Plug a hole this year with a second round pick, let a couple of contracts come off the books and evaluate exactly what we have, ie, Schultz, yak, Landers,even Mcdavid. The window opens next year when there will be even more cap room to go hard.
    I would like to see a number one D this year and see what we need by December.

  • Igor Ulanov 55

    Just to be clear, are we saying a projected 90million dollar cap is going to make problems for this team? That was projected at the lockout, and despite the cap not jumping huge this year, the projections are still in line.

    Nurse and Drat can be bridged cheaper as rfas, and we could lowball klef now. Yak will also probably be cheap. We could pay 56 million (probably could cut that down even) to our best 8 players, and still have 34 million for the other 15. The skill up front probably makes the 4line irrellevant.
    Hall, mcdavid, yak probably play 20ish min
    Pouliot RNH ebs probably play similar
    Draisaitl Lander xxx could play 15+
    4line won’t need that much time. We could pay league min for those bums

    If defence has Nurse and klef eating 25+ min a night, and a second pairing can play 20ish (say Marincin and 16OV or fayne), then you can have a largely irrelevant 3rd pair like chicago. Not to mention, 3rd pairing guys don’t cost 4million on regular teams (Grrr MacT).

    I agree that the time to win is fast approaching. Problem is we are coming from a long way back. There are contracts that are problems for this year, but come off the books next (scivens, nikitin, purcell, etc). McDavid, Draisaitl, nurse are all rookies. McDavid could reasonably be penciled in as the 2C we needed last year, but now we are short a winger (Perron). We also flushed Petry, which means we need two top pairing fill in type dmen instead of 1. Defence is waiting for Kbomb and Nurse to take that top pairing. Only way it is going to get fixed without destroying another part of the roster. We see this over and over again. Oilers desperately need what they just traded. Move Eberle, and all of a sudden, yak stuggles, and we have no top six RW. This is the problem with trades. Not to mention oilers players are drastically undervalues on the market.

    I would try to target Cam Talbot with the MTL 2nd (I would part with the 33 but not the 16). Run him and Sievens, so you can at least afford a dman (his cap still counts if he is sent down, and a ufa G would be paying two guys). Take a run at a Sekera or two. Maybe pick up oduya, or swipe someone cheap from a cap team.

    MacT left a lot of problems for Chiarelli, and it is going to take more than one offseason to address them. Luckily many can disappear by 2016. I don’t think of next year as more of the same, but it has to be trust in McLellan, and smaller bets that push us forward. It is still kind of a reloading year. We are waiting on Nurse and Klefbom more than anything. If you can trade ference, Nikitin and Jultz aren’t that bad (except when together). I’m saying just patch the holes, don’t try to fill them yet. 3 solid pieces could push this team to the playoffs, if we don’t subtract anything.

    Blowing our brains out will just limit the window we have. I believe the cap will be manageable at least until Nurse and Draisaitl hit UFA. The 90million is a realistic number by the time of the Hall extension.

    • BabyNugeMonitor

      Not to mention, McDavid might take a crosby discount, because of all the sponsors he has. Money won’t be as big of an issue to him as it is to other players. Buddy wants to win.

      • Cheap Shot Charlie

        McDavid to take a discount to stay on in Edmonton? HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA. That’s the stupidest thing I have ever heard. “I am the alleged best player in the World, but am happy to stay in this dump and keep playing and forego multi millions of dollars I could get in any other kick ass city in North America”
        What ever helps you sleep at night man, lol

  • Word to the Bird

    The Oilers have to get a top- pairing dman or it will be the same gong show as always. Even worse, if they don’t improve on the backend it will impact the development of Nurse and Klef. Hopefully they can get it done with this year’s 16th and next year’s first rounder. But if it requires trading one of the core players, let it be done. It would be great to have three real options at centre, but as of today they don’t even have a legit top-four dman, let alone a first pairing guy. Waiting and praying for our blueliners to develop is a fool’s game. People talk like Nurse and Klef are a slam dunk. Just ask Tuebert how that went. Or talk to Cowan in Ottawa. Just get a real dman.

  • RandomScrub

    Really? Two D and a goalie? that’s going to propel the Oil to Stardom? If it’s that simple, then every team can be Stanley cup contenders! Chiarelli has a plan, and I believed him! To make the team plays like a well oiled machine first, to play hard, to play smart hockey for 60 minutes; then, he’s going to assess what he need to add on to make the team go over the top; It could very well be 2 D and a goalie, it might not, but at least when the reinforcements come, it will be icing on the cake, for sure!

  • sportsjunkie007

    I understand Matt’s frustration as we all share it. I certainly agree that we should use all our top draft picks after McDavid to try and shore up the holes we all agree must be filled. The problem is that to do ALL of that we will likely have to trade a core player and the new people running the Oilers do not know those core players well enough to decide which one to move. I would rather they didn’t rely on the judgment of Lowe, MacTavish and Howson for that, although they have hopefully pumped Nelson about it. I believe Chiarelli and McLennan will be demanding more from these core players and will want to see how they respond before shipping one of them off. Besides, players such as Yak, the most logical core player to go, do not have much trade value at the moment.

  • Igor Ulanov 55

    The fear would be landing Seabrook now and getting two good years and then five bad ones and being trapped in cap hell. Look at Boston.

    If any team has embodies the “conservative” appoach it would be Detroit. They managed to put together a solid team through good contracts and didn’t have to rely on making big free agent deals.

    It’s not a case of the Oilers becoming “magically” good. Waiting will actually fill some holes in the current roster. Klefbom and Nurse are going to be developing for this season and Draisaitl and McDavid are going to come online and only get better while the current core is still under contract.

  • PEBOisONit

    Wow, with McDavid the oilers have been given a second lease on life, haven’t they? Unbelievable. Don’t get me wrong, I respect Hall, Nuge, Yak. But for years we could be ruing that we didn’t get one of the true generational number ones, that we just missed that boat due to sucking at the wrong time. Who could imagine that even after all these chances, they’d still get a player like this?

  • Kevwan

    There is a combination of key talent being too young and inexperienced and too many vets on bad contracts. As frustrating as this is, time will cure both problems. With a few moves this summer and more next year the window should start coming into view in ’16-17.

  • Zarny

    Outstanding article.

    I don’t think anyone who says the Oilers should hold back on big moves understands the concept of windows.

    I think you can argue a window to win appears once you have a few elite, skilled players.

    The problem is that windows are like doors. You have to open them to go through. That requires action.

    The fundamental problem with the Oilers was the complete inaction and lack of care to the roster for a few years. The time to add players like Fayne, Pouliot, Gordon etc was 4-5 years agp not 1-2.

    The Oilers’ young players aren’t behind schedule; everything else is because management took their foot off the gas.

    Eberle is 25. Hall is 23. Nuge is 22 and Yak is 21. The time is now. The supporting roster should be good enough to make the playoffs right now.

  • RandomScrub

    Hear hear!!! The rebuild ends this summer! Chiarelli can find those 3 peices and this team can move forward. The best thing about the management change is that the new guy has nothing to lose by trading players that previous GMs didn’t know how to rationally evaluate. Get it done!!!