Well ... it wouldn't be good, but I can see how that could work. I would be happy to die for someone I loved too.

[ Perhaps Jack should tell him no definitely that he shouldn't want that or it would be terrible, but he is the wrong person for it. Jack is very like his father in that he's ready to die for his loved ones without thinking about it. He was turned into a bomb ready to explode for his family, and he didn't have any regrets about it outside of he didn't fulfill his obligation. He burned his soul out for them, he was ready to sacrifice his life to Dean to end it in retribution.

Jack wants to live but he also isn't afraid to die. A part of him does think it's better if he dies, for everyone. He is too dangerous to stay alive and while his family loved him, they suffered for him, and he stressed them out. His very existence makes every day more complicated. Sam and Castiel weren't ready to accept his death to take out Chuck, but Jack was glad to get a reason to make amends for Mary. ]

I was thinking if I survived destroying Chuck, I could go get you. I'd have the power. The Shadow does like me, enough to maybe plead my case.