I wouldnt call Pietrangelo nothing..

I made a suggestion that a deal like this could work for both teams a little while ago, its not for Pietrangelo but instead for Parayko, but both players could have similar trade values. I just feel like Parayko is the better fit for Toronto with his size and more defensive game, and St.Louis could use more prospects if they go into a rebuild. Lemme know what you think, I also compared it to the McDonagh trade. Keep in mind that Zaitsev has to be included for cap reasons:

ST.LOUIS GETS:
Jeremy Bracco
Nikita Zaitsev
Rasmus Sandin
2019 1st round pick (TOR)
2020 2nd round pick (TOR) *Conditional - becomes a 1st round pick in 2020 if Leafs win the Cup in either 2019 or 2020

TORONTO GETS:
Colton Parayko
Zachary Sanford
2020 4th round pick (STL) *Conditional - Leafs get pick if Toronto 2020 2nd round pick is upgraded to a 2020 1st


Keep in mind that a "low" 1st round pick got St.Louis Klim Kostin at 30th overall a couple drafts ago, so it's not as much about where the pick is its about how you use it.

The value is pretty good, but retooling teams tend to move rather their veteran players than young established ones. Parayko's only 25 with 4 years left on a good contract - even a rebuilding team would keep that kind of asset... I'm quite sure they'd rather move Pietrangelo, who's a tad older and has only two years left on his contract...

Agreed, rebuilding teams do trade veterans. But they also tend to move their core players and get the most value back. I feel like since there's the chance that Pietrangelo could walk in 2 summers diminishes his value more. If Parayko stays for a full rebuild he's realistically 30 years old when they're ready to contend, and then he's past his prime. So why not get as much value for him as you can when he has term on his contract? St.Louis might rather move Pietrangleo, but Parayko may bring the most value back to help the rebuild move quicker

Blues won't go full rebuild for the reason you mentioned. Parayko is younger than Tarasenko, ROR, Schwartz and he would be too old by the time we were rebuilt. The Blues will move a big name but will try to get back into the playoffs as soon as possible. It's not like our core is that old and it's not like we desperately need prospects. Just need a shakeup involving a core player, a new coach, and some goddam goaltending.