Why would they have traded him? For the majority of the season Boston was the best team in the league. They missed the President's Trophy by 5 points. They were going for another cup and had a great chance at it.
They are a little paper tiger right now. Maybe that improves with Lindholm but they really have two elite players in Pasta and McAvoy.
They are a bit in that limbo stage that the Wings were post Lidstrom. I think they have some better young players than we did at that point though and its easier to stay in the playoffs with defensive depth/goaltending than it is when your strength is forward.
I think Boston has 2 seasons where they can play around and see if they can find the youth/free agents to build a real contender around Pasta/McAvoy but if they can't do it and hold out longer then that you probably end up with the Wings style rebuild. In 2 years at 29 (Mc) and 30 (Pasta) you still have highly tradeable assets that will be worth a ton and really give you a jump on a rebuild. I don't think you lose a ton of assets by hanging onto them for a couple of years and seeing if you can retool.
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As for Ray I would lean towards just locking him up for 8 now. That takes him to 30 and gives us his prime years. His game isn't reliant on any one physical skill so his potential for regressing is less. The Wings have no other star contracts that they have to manage around except Seiders. Like I could advocate around Ed maybe getting a bridge deal in a few years if Ray and Seider already have large contracts. I don't hate a bridge deal for him, but I feel like the only way to justify it is if the Wings had used that extra cap space to improve other areas already this off season. If the Wings enter the season as is, there is no reason to not lock him into a longer term deal.