Board Thread:Versus Debates/@comment-1018594-20150608074819/@comment-26537507-20150629164309

Fearlandscape wrote: If Kakashi were able to best Jiraiya, he would have been the one getting offered the Hokage job all the time instead of Jiraiya. Also it was Jiraiya who went to the Rain Village to investigate Akatsuki leads, not Kakashi.

Little things like this tell you all you need to know. To be fair though, at that point I think Jiraiya was only affiliated with the Konoha, only visiting when he had business there. Kakashi on the other hand, was a more integral part of the village, he still was given missions and had duties to perform inside the village. Also, Jiraiya had tasked himself with finding out about the Akatsuki, who they were and their purpose, part of which involved going to the Rain Village. It wasn't as if Kakashi was given a mission to go there and turned it down. That being said, if I had to choose one of the two to send, I'd send Jaraiya since he's more skilled and experienced.