Those Montour and Toffoli contracts are insane, even for an incentive dollar value to come to a rebuilding team. You’re shooting off the mark by 3-4.5 mill on each deal.

How does this help the Sharks. With that big of a contract even 50% retained isn't going to be easy to flip.

Sharks have no retention slots available either

The idea wouldn't be to flip them (Sharks have already maxed out their 3 retention spots for next season). It would be to provide some stability to the team next season with Celebrini, likely Smith Mukhamadullin Musty Graf, maybe Gushchin Thompson all on the roster next season, and give them as good a chance to succeed as possible (by way of further development via NHL minutes), and to do so without re-crippling the team cap-wise in the long-term.

Sharks are in a very interesting position this year with their cap situation and young players. If Grier does the mundane thing and hands out a 3x3 to Kunin and a 3 year deal to Stamkos (whom fans will rejoice at but who won't actually move the needle for the team), it won't be in the best interest of these young players. Sharks don't need their young players to try and carry a weighed-down team. They need a decent team who can support their young players so they can develop.

Not what I would do but I would expect SJ to overpay an older winger and a steady D man to help out. Overpay on a short term deal to do so