Quoting: OilersJeff
Barrie is absolutely awful. He's horrible defensively and Bouchard easily replaces him as a better 5v5 point producer on the right side who, if given the chance, could likely produce at the same rate on the PP. Barrie gives up way more than he produces and it's not even close. As far as not going all in this year, when is it that you're going to do it then? The Oilers are backed up against a wall in terms of cap space for next season. If they can get solid goaltending I don't see any reason to not go all in.
Pretty much common sense you don’t go for it all unless you’ve shown you can actually make a run. Once the Oilers show they are consistently going beyond the 1st round; then those 1st pick rentals make sense.
When you have the two best hockey players in the planet on your team, you aren’t thinking about winning one cup. They want to win a few. I get that you gotta win one before you can string some together, but if you put yourself in a position where you don’t have the 1st round talent in your prospect pool coming up once you’re already at the cap limit and your rentals have moved on, that’s not exactly good news. You don’t go trading all future picks when you’ve made it past the 1st round once in the McDavid era.
Pretty much exactly what Tampa did. After a few years of being a top team in the league but not winning it all, they made the moves using their 1sts to push them over the top. Not to mention, they got cheap, high impact players with term left.
Moving the picks like you suggested is nothing short of reckless.