Re: Could Jiraiya Have Defeated Pain?
Jiraiya fought at the worst place for a normal shinobi: a series of connected sewer tunnels, with one path of vision. Pain had 6 paths of vision, easily knowing where Jiraiya would be hiding.
Naruto's fight with Pain was on a flat, wide open environment. He could see all 6 Pains right there! He had tremendously-less worry about being flanked.
Knowledge is one thing, but having to fight in a seriously-biased territory is another thing entirely.
Despite this, Jiraiya incapacitated two Pains and took one home. Were Jiraiya to fight on the same grounds as Naruto's fight, he would have progressed much farther to the final Pain, then lose.