Let’s do the Tampa approach trade for Jack let him get his surgery so he can be back for the playoffs (Likely do this trade around the deadline and surgery after).

Now the key part the leafs trade him (or Marner) at the Draft before Jacks NMC kicks in this also allows them to recoup the assets they spent to get him or close to it.
Jack gets his surgery and other teams get to see that he can still play which is one of the big hold ups