More on Gabriel and Sibling Dynamics: Pacifism,...
Class clown – like Dean trying to defuse the tension between Sam and John? Without much luck or thanks from either. Sam sees it as Dean taking John’s side (the status quo) and John as rebellion (trying to interfere with the chain of command.) Bet Gabriel can identify with that – the hopeless struggle to keep them all together.
He definitely can relate to that, but I think the point of departure is the way that Dean and Gabriel respectively deal with acknowledging that hopelessness. Dean keeps pushing, even to the detriment of all involved, subjecting everyone around him to his idea of “what’s best for them.” Gabriel, on the other hand, withdraws from the situation and the people involved altogether, because he believes that his involvement can help in no way, and in some ways, even hinders: with the result that his loved ones feel abandoned. It’s the difference between being too controlling and being too passive.
Incidentally, it’s also why Michael and Gabriel could never be allies, because Dean is remarkably similar to Michael in many ways, good and bad.
And I think it makes Michael’s murder of Gabriel particularly poetic, because it was in good part Michael’s “sword” and “perfect vessel” (Dean) who nagged and pushed and harassed Gabriel into feeling like he “still owed” the factions in the Season 13 feud a (pointless, heartbreaking) sacrificial act.