Like most finale-related discourse, I’ve been trying not to think about the fact that Sam named his son Dean Jr. because I just hate it so much. I just really hate legacy names!
However, I think it would be absolutely hilarious if Sam and Eileen also hated legacy names. Like they are so done with that now. They’ve had their whole lives pulled this way and that by God himself, toyed with, their parents murdered when they were babies, for no good reason. So, you know what? Screw being legacies! They are not here for that anymore! And neither are their kids.
However, I’m going to just throw a curveball in here and say that maybe Crowley just so happened to sneak out of the Empty when Jack was resurrecting Cas (because I miss the little fake-British weasel, okay?). And upon discovering that his mother had taken his throne as Ruler of Hell, Dean and Cas were shacked up in heaven, and that Sam was married to a pregnant hunter on earth, he decides to pay a little visit. He ends up being the one to drop the idea of naming their tot after Dean - maybe because he thinks another Dean Winchester running around out there would be fun to mess with? But we all know Sam took Eileen’s last name so probably what’s more likely is that it’s because he knows Sam would just hate the idea, but that he’d get all doe-eyed and tongue-tied in a way that was maybe just a little misleading to his wife.
And he does. And just like that, Eileen thinks that it’s something that would make Sam happy, so she’s agreeing to it so enthusiastically (despite her own wishes) hoping to make her husband smile again. And now Sam thinks that Eileen loves the idea so how can he say no??
Crowley manages to keep his smile neutral until he leaves the house, and then he’s grinning like the cat that got the cream. But could anyone blame him? It was his Hell-given right to mess with the Winchesters every once in a while. He’s not too sure if they’ll actually fully go through with it or not, but Dean’s death is still very recent and so it’s a sensitive topic that they struggle to talk about, so neither of them actually realise that they both hate the name! So, several months later, out pops baby Dean.
It take several years and a lot of internal cringing and wincing before the truth finally comes out on Dean Jr’s third birthday. They laugh about it and debate whether it’s too late to change it to his middle name now instead.









