CHI might accept that. But they probably want the 2023 2nd instead of the 2024.

Simply not enough for SJ. Easy pass

Ya I could see more being needed to make this happen. My train of thought was the following:

2023 1st round pick (very valuable)
Reid Shaefer (2022 1st round pick)
Raphael Lavoie (decent prospect with hands and size)
Jessie Puljujarvi (cap dump)
Tyson Barrie (Having a great season and SJ flips him for a 1st at the deadline)

Essentially 3 1st round picks + prospect + $3M Cap dump

Barrie loses value the second he is not on a PP with 97 and 29. See barrie circa Leafs

If Columbus can get a 1st round pick + for Gavrikov (reported asking price) for a UFA who is pretty average overall. I'm pretty sure Barrie who has offensive upside regardless if 97 and 29 fetches a 1st rounder.

Barrie also has term at a reasonable cap hit. Not many defenders with his skill-set.

Leafs just wasn't a good fit. They had Rielly on the PP so his role was diminished. He did great in Colorado.