a) The whole "we should have paid for extra retention" thing might be moot anyway. Iirc, Grier said there were two teams at the end, and the other wanted more retention, and they didn't want to do retention.
It is entirely possible that we could not have competed the move with more retention - that it would have let the other team outbid us. Or that San Jose's price would have been extortionate, or that they'd said no to Granlund... you get the idea.
50% is just not on the table. At every turn the words of the media and the Sharks have made it clear that wasn't on the table. And if it was, the amount of teams bidding for Erik Karlsson at 5.75m goes up drastically, as does the asset return possible, which is a losing proposition for us.
b)
Need that pick for what? We won't be ready to ramp it up for playoff entry again until like 2030, if not later. By that time the pick will be 25+ and nearing the end of the allowable ELC period, if not past it. He may not even be on the Penguins anymore.
Similarly, what do Yager and Pickering do for the Pittsburgh Penguins, and when?
What we need are like 2026, 2027 and 2028 picks, so their development matches our ascension timeline.
We're not tanking this year or next year IMO. That's just not happening with the big 3 and Dubas being new on the job. Summer 2025 at the earliest is when the dismantling starts.
There's two things you would like that '25 1st (and so on and so on) for.
The first is just good old you never know. You never know when a prospect is going to blow up. You never know when you're going to be crap sooner than you expected, or get lucky in the lottery. Or decide to put trade protection on a pick, trigger it, and find yourself handing over the '26 1st instead. There's already 276 posts on Gavin McKenna. Or you never know when you're going to be better than you expected sooner either. Both Ottawa's and Buffalo's rebuild accelerated suddenly due to unexpected circs.
Obviously you can't just sit there doing nothing because of "what if" but teams that don't enter jackpots don't win prizes.
Second, and more certain, is that prolonged rebuilds are really hard to come out of. The instilled losing habits, the lack of talent with which to guide youngsters into the line up, the lack of assets to sell off... sure, you've got to hack and burn to allow for new space, but take it too far and all your new plants start dying.
Having some meaningful young players somehow when the time of Crosby is done is going to matter. Even if they're not part of the next contender, being able to sell them off will help a lot.
Obviously we're probably going to sell off that 1st at some point... but we are still selling something meaningful that could be incredibly valuable to the org.