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.