Sometimes I like to think that Jack knew the whole time what will was planning bcus either way Jack knows this will be the end right? Maybe deep down Will is his guy after all and will do the right thing which if so, great, but also Jack aint no fool, he just has shitty ethics and methods so he knows that he can trust Will to bring this to an end regardless if Will comes back to him, dies or not
Jack certainly isn’t naive, but I think when it comes to Will he truly believes in the best of him, even when he maybe shouldn’t. He believes that when it comes down to it, Will is always going to do the right thing (
even after that one time he called the Chesapeake Ripper and warned him to run before the FBI could catch him… Oh Jack…) This is why he knew Will would help him when he came knocking after all those years. Even at the expense of his own psyche, he knew Will would say yes.
Jack understands that Will and Hannibal have a bond, no doubt about that, and I think to a certain extent he even understands how deep that bond runs. I just don’t think he realizes how unbreakable said bond is. Will can’t simply “cut that part out” as Jack advised him to do in Dolce. But in a way he wasn’t wrong to believe Will was his man in the end, he did take Hannibal over that cliff after all, it’s what comes after that is really going to push Will firmly into one corner or the other.
In terms of what Will’s plan was though, I don’t think he actually even had much of one to begin with. He certainly set things in motion with Dolarhyde, and with planning the fake escape, and with very pointedly not telling Jack about his encounter, but everything that came after was borne mostly out of circumstance. That doesn’t really matter at this stage though, Jack’s biggest mistake was not insisting on being there himself, at Will’s side, because allowing the two of them to have that moment was basically guaranteeing that wherever they end up after, they will certainly end up there together.
So I guess where Jack and Will differed in the end was Jack’s ideal plan was: Will lures dragon in via Hannibal, Will kills dragon, Will kills Hannibal, Will walks away unscathed and goes back to his family, Will and Jack are totally awesome heroes taking out two bad guys for the price of one. Whereas Will’s plan was essentially: Set the thing in motion with Dolarhyde, only let Jack know as much as he needs to because lol fuck that guy, ¯\_(ツ)_/¯, hope for the best??????, smack talk Bedelia for a bit because that’s the most fun an empath can have with his clothes on, totally convince himself that he can watch Hannibal die (because that’s gone so well for him in the past), probably subconsciously hope that he and Hannibal get to do the killing thing together, ???????????????, profit.
One of my biggest hopes for season 4 right now is for Jack to track Will and Hannibal down, because that is one post-fall encounter I need more than air at this point.