If you can get past the fact that he's an Edmonton guy, Tyler Dellow is maybe the best single hockey blogger in this country right now and he tackled this topic yesterday.
Quote:
Originally Posted by Tyler Dellow
 Looking at the guys on whom teams went long right away, it’s hard to find any cases where the team would be unhappy with how the contract worked out. The Ovechkin deal has some potential to be a stinker but Washington could have done a deal for half that length and Ovechkin would probably have a lot of value in a trade right now if they had, what with just having won the Hart Trophy.
[...] My hope is that they go to eight years with him and that if he’s trying to do a shorter deal that they don’t bite. Look back at that list of high draft picks who did five or six or seven years and ask yourself: in how many of these cases would the team have wanted to be able to extend the deal for the same money? I’d suggest that the answer is: all of them.
Anyway, my basic points are these: bridge deals with top five draft pick forwards who’ve produced aren’t really the way that the NHL has gone, regardless of what you might hear. If we can learn anything from the surprisingly reasonable Duchene extension, it’s that you might be able to get a very reasonable third contract even if you do the bridge deal. That said, the Oiler die are kind of cast on this with Hall and Eberle having been paid and getting a third guy into that structure hopefully makes things a bit easier with Yakupov when the time comes. If the Oilers get RNH and Yakupov onto the same sort of deal as Hall and the three of them produce like first overall draft picks, there’s a better than average chance that they’ll end up with a three year window towards the end of Hall’s contract in which they’re paying $18MM for talent that would cost a combined $30MM on the open market.
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http://www.mc79hockey.com/?p=6281