i wonder how it might have changed things for jack in s14 if cas had told him about his own struggles with too much power (godstiel era), or sam had talked frankly with jack about his experience with soullessness. jack responds well the times that they do relate to him with specific experiences. for example, cas telling him about his own experience with gracelessness in 14.02 gods and monsters, or dean connecting with him over the grief and guilt they feel for the people they couldn't save in 13.23 let the good times roll. the deck was so stacked against all of them at the end of s14 and chuck was actively pulling strings, so maybe it wouldn't have changed anything. but maybe it would have helped jack handle it all? it at least would have been good family moments
