Hindsight:
I mean, we did "soft tanking" all the years. 9,13,9. Where would we be with actual tanking?
2011: sell Ladd, Byfuglien, Enstrom at the draft, maybe get 3 first round picks out of it.
Best case mid-late first round with today's hindsight: J.T.Miller, Oscar Klefbom, Boone Jenner. Maybe Chevy does a homerun and picks Brandon Saad. Doesn't look like a deep draft today.
2012: pick top3, get Yakupov/Murray/Galchenyuk instead of Trouba
2013: good draft. Pick top5, get somebody like Barkov/Jones/Monahan instead of Morrissey.
2014: pick top5, get somebody like Draisaitl or Dal Colle instead of Ehlers.
Fail to attract any free agent in the process because we're a bottom5 team in the prairies. Would we be in a better position now?
Hindsight #2:
Chevy made one decision which actively hurt the franchise going forward: signing Pavelec. And then the Noel stuff.
Some argue that not using a compliance buyout was another one, but we can't look behind the scenes, maybe it was not an option.
Some swings and misses: a second round pick for Lukas Sutter, a second round pick for Devin Setoguchi. Both only did minor damage, as missing with a second round pick is pretty normal.
Not providing depth: well, every decent UFA found a franchise to play with. Maybe we just couldn't get good depth.
Hanging onto Kane: we don't know the offers.
Stuart/Thorburn contracts: that's really minor stuff. Every team has at least 4M locked up in "bad" players.
Why this offseason counts a lot: Chevy can make moves that hurt the franchise going forward. Handing out albatross contracts (Ladd, Byfuglien, even Stafford), or not clarifying the Byfuglien/Ladd situations, eventually losing them to UFA. Losing the newly found attractiveness for free agents (WPG=playoff team) by not being able to fill the forward holes appropriately. There's even the possibility of trying to win too hard, trading assets for 2 or 3 vets like Patrick Sharp.
We have every right to be nervous.