Honestly This Is Just My Opinion And Point Of View…

The Headbands Ninjas Wear Symbolize who they are Loyal to. It even has Powerful symbolism as when ninjas go rogue they deface them to show they are no longer to loyal their villages. Though it’s not officially stated, my fan speculation is that jiraiya uses his own symbol, “油” {oil, which means his training at Mount Myoboku at a special fontain of oil he become the toad sage} To make other contries More Welcoming of the traveling jiraiya. when jiraiya was yonger and participated in the ninja world war he wore the hidden leaf village headband as a soldier a and Fought ninjas from other countries. Though the Naruto series starts at a time of relative to peace, chances are anyone wearing a hidden leaf village headband in hidden Rain country would be met with unpleasant reminder’s of the war fought not too long ago. as jiraiya had now dedicated himself to traveling through various countries as a sage and not a soldier of fire country, he wears a politically neutral symbol. Or maybe the 3 Hokage asked jiraiya to stop wearing the hidden leaf village headband to bawdy establishments?

Well he is a sage of Mout myoboku who is also a sannin of the hidden leaf village. He is not a regular shinobi you can give random missions too. He has have own rights and can do as he wish. so, this might be the reason why he decided to keep that headband. And he is also know as a great spy , so in order to aviod any trouble when spying on different countries jiraiya have choosen to go with that headband. not many in Naruto are aware of Mout myoboku’s existence and they might not suspect.

Well, this not the Headband that a shinobis wears, the symbol on the forehead protector is the “Abura” which as you stated means Oil. he wearing it on his Forehead protector represents his affiliation to it . The Symbol probably comes form the special sacred oil, which allows people to feels natural energy More easily, and evaporate outside Myoboku’s atmosphere. this symbol actually gives him “Chi” he required for the senjutsu and also point to his oil spitting for ninjutsu oil. I research Futher and Found out that in Japan , abura no gama is a type of medicine effective in treating cuts, burns and bruises . Those again signaling thoward senjutsu.

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