When Jiraiya went to Amegakure to investigate rumors of a civil war, part of him knew after his talk with Tsunade he wasn't coming back.
Tsunade knew what Jiraiya was doing to himself. She knew the Akatsuki leader was too powerful for him, but yet, stubbornly, he still decided in the end he would be going.
The mission he assigned himself to had no valuable meaning. The only reason he was making a dangerous trip to the Land of Rain was to confirm certain rumors.
And yet, as he gathered intelligence on the Akatsuki leader, he would have never expected it to be the student he trained years ago.
After sneaking into Pain's hideout, he encountered another one of his students. She was the partner of Pain, known as Konan.
After finally seeing his student's face, he saw just how much he changed. And to start things off, he brushed the student-teacher bond aside with cold indifference.
They began to fight, once known as student and teacher, now worlds apart. They exchanged blows with multiple summons of their own making.
Pain summoned animals of all sorts, while Jiraiya stuck to Gamabunta.
Jiraiya prepared a fire technique, along with Gamabunta's oil. Pain did the same, until he unexpectedly blew massive quantities of water at the fire. Jiraiya didn't see this coming, and was hit by the water.
Pain, meanwhile, stood on top of his summon.
"I see you haven't grown up."
Jiraiya looked at Gamabunta, and he knew it was time to disappear. Jiraiya ran from Pain, but Pain's summon was too fast. Pain sliced his former teacher in two; only upon realizing it was a clone, looked around for the sannin.
"It worked." Jiraiya said
He managed to create a shadow clone while they were exchanging their fire techniques. He did see Pain's water attack coming, but decided not to dodge it for this very purpose.
Out of nowhere, Pain summoned one more Akatsuki to disperse and find Jiraiya. Due to their battle, Pain's hideout was ruined, which allowed Jiraiya to make a getaway in one of the pipes.
With this extra time, Jiraiya called upon his Hermit Mode, which consisted of two frog elders who would aid Jiraiya in his battle with Pain.
"This delay tactic won't work for much longer. Time to come out." He made an opening by breaking the pipe
Jiraiya hid behind a damaged wall of Pain's hideout, and watched the two bodies of Pain.
"Are you ready?" Jiraiya quietly asked
"Yep. Whenever you are." Pa Frog said
They finally revealed themselves, with Pa Frog shooting an immense amount of water in the sky, which was followed by a fire technique by Jiraiya.
Finally, Ma Frog shot out a bolt of lightning, creating a colossal rainstorm all over Amegakure, with the crashing lightning all over.
Pain watched as the skies quickly darkened over Amegakure.
"Impressive technique, sensei."
Jiraiya controlled the lightning at his own will, and commanded it to go right through Pain's skull, but the two bodies instantly vanished.
"Teleportation?"
The lightning went to the place designated by Jiraiya, but by then, Pain was long gone.
"He didn't make any hand signs at all. If what I saw is true, then his space-time ninjutsu is even more advanced than the Fourth's!" Jiraiya said
As the fight carried on, Pain realized he was falling behind with just two bodies, so he summoned two more.
Pain unleashed techniques on his former teacher that were beyond human comprehension. And never seemed to run out of chakra.
Finally, with the four bodies, Pain stabbed Jiraiya two times near his heart. He also pinned Jiraiya and his two summons, preventing them from moving.
"It's over. I've pinned to the ground. You, nor your summons can no longer move."
What happened to him didn't matter now.
"If I do die, I know there's a student of mine who will continue what I have left." Jiraiya said
When Jiraiya freeing himself from Pain's technique, he was stabbed two more times. Jiraiya knew it was over after that.
As he lay on the ground, only one thought came to mind.
"Naruto…it's all up to you now. There's not much time left for me." He felt himself dying
Pain watched his former teacher dying from a short distance.
"I see now." Pain looked at former teacher's face
"I'm passing…out…"
Jiraiya began to recall his entire life, as well as he could.
He remembers how he was once a team with Tsunade, Orochimaru, and Sarutobi.
He remembers the bell test, and how he was put on the stump.
He remembers the day the three of them fought Hanzo, and how they finally earned the title of "sannin."
He remembers the day he met Nagato, Yahiko, and Konan, how he took care of them and trained them.
He remembers the day Orochimaru fled the village, and how he failed to save him.
He remembers teaching Minato when he was a child, and the day Minato died sealing the Nine-Tailed Fox inside Naruto.
He remembers the day Sarutobi died in his fight against Orochimaru.
He remembers not being able to convince Tsunade in love, not being able to save Orochimaru, and regrets not being able to save the Third or Fourth from death.
But all those things didn't matter as much as the student he knew would continue on what he left behind. If he didn't take on that student, he couldn't die peacefully.
Because of taking Naruto on as a student, he is able to let go of this world, and so he would.
Pain meanwhile, just continued staring at that dying face.
"It's all clear now, sensei."
"I guess…this is the end. But before I go, there's one last thing I need to do."
Pain didn't care what his former teacher did now; he would be dead in a few seconds.
"Get back to the Leaf."
"Got it!" The toad said
Jiraiya watched as his last hope of figuring out the mysterious Pain left the war-torn battlefield.
"Naruto…good luck…I know you'll succeed…"
Pain continued walking away, until he was met by an Akatsuki member. It was Zetsu, who decided to meet Pain once the battle had reached its end.
"You shouldn't be so careless."
"There's no need to worry. I saw what he did. Even if that toad did get away, it won't matter. No one can defeat me."
"Not even the Nine-Tails boy?"
No answer from Pain.
"There will be a time for everything."
Pain formed a hand sign to his face, making his other body disappear.
As that happened, Pain and Zetsu made their exit from the battlefield which was carried out by a once student-teacher bond.
The future was near.