dear sannin enthusiast, what do we think about jiraiya not wearing a standard forehead protector? his loyalty to toads surpasses his loyalty to konoha, but he threatens to kill tsunade if she sides with orochimaru (against the village)?
THIS IS SUCH A GOOD QUESTION, and it's one I've been considering myself because Jiraiya's loyalties are something I've been analyzing lately (been trying to write a post and this seems like a good time, thank you for that)!
Whether Jiraiya is more loyal to the toads or to Konoha is a question I've personally been mulling over, and I can completely see why him being more loyal to them is your conclusion. It makes sense! The headband, the fact he learned so much from them and works with them so often, and has for so many years. Fukasaku even calls him Jiraiya-chan, much like a father figure would. Since we never see any of Jiraiya's biological family, it's easy to sub the toads in as his family.
However, even though Jiraiya is close with the toads to the point where he outwardly signifies himself as one of their ranks, there is still a part of him that remains steadfastly loyal to Konoha. He still does missions for them, spies for them, and as you pointed out he was even willing to kill one of his oldest friends to prevent the village from being betrayed. He may be a toad ninja in all practical ways, but there is still that core piece that is willing to kill and die for Konoha.
And, as with a lot of characters in Naruto, we have to wonder why they're so damn loyal to the village. There's the propaganda of course, but it has to start somewhere besides that. In Jiraiya's case I believe that chiefly, his loyalty to the village stems from a loyalty to Hiruzen himself - loyalty and a desire for his teacher's approval.
We see in flashbacks that despite being more skilled than your average kid, Jiraiya still struggled to keep up with his teammates. Unfortunately, Hiruzen is not shown to be supportive or encouraging towards him but instead answers with physical punishments - a punch to the head, tying him to a stump, etc. I'm not sure how Jiraiya ended up in a hole in this most recent picture but Hiruzen sure isn't helping him out.
It was around this time that Jiraiya first made contact with the toads and began his training with them, at which point he started to improve. This is likely an intentional parallel to Naruto's training being passed from Kakashi to Jiraiya. In Naruto's case this was due to a variety of factors, including his immense chakra needing to be mastered. In Jiraiya's case? No idea! Hiruzen's just lazy I guess.
One would think that this treatment from his teacher might have fostered resentment in Jiraiya, but instead he's easily the most devoted of Hiruzen's students. We see this displayed in a variety of ways:
In group flashback shots, Jiraiya is shown copying Hiruzen's expressions - note the eyebrows on both of them in that first pic.
When the Sannin were adults and no longer training under Hiruzen, Tsunade proposed expanding the medical ninjutsu field and building a hospital, Hiruzen was quick to shoot her down (which is another infuriating can of worms). Jiraiya is sitting right next to Tsunade during this meeting. She is his close friend, he apparently has a romantic interest in her, and he knows full well how competent she is with medical ninjutsu. And yet, he stays silent and does not speak up in this moment - the only reason I can give is that he does not want to go against Hiruzen's decision.
(sidenote: Dan, who is basically a stranger to Tsunade, speaks up instead and this leads to the two getting together. You really dropped the ball here, Jira!)
And of course, Jiraiya is visibly angry when Tsunade calls Hiruzen a geezer and mocks his death. It's clear that it heavily affected him; he's also the only one of the three to openly mourn him.
So yeah, I know this got a bit long-winded, but the general point is: Jiraiya may be a toad ninja in all ways practical, but at his core he is still a Konoha ninja, and even deeper there's a part of him that's still a little kid who just wanted his teacher to be proud of him.
Orochimaru hit the nail on the head with this take.
