AND HERE WE GO!
You may not know this, but Jiraiya is a genius.
One of the strongest shinobi ever to emerge from Konohagakure, Jiraiya has denied the position of Hokage at least once. He was one of the most influential shinobi ever to live, not just in terms of political clout within his home village, but in the effect both he and his students had on the Shinobi World.
Of the people taught by Jiraiya who grew to adulthood (and one who hasn't yet) all four reached S-rank. In terms of direct tutelage he is incomparable, if you measure through results. Even his own teacher, the Sandaime Hokage, only ever trained three S-rank shinobi.
Jiraiya was a master of fuuinjutsu. He taught the Fourth Hokage, (nearly) universally agreed upon to be in the top 5 in terms of intelligence. Minato's meteoric rise through the shinobi ranks was not least a result of Jiraiya's teachings. His achieving the position of Hokage as young as he did, even against an opponent like Orochimaru (Hiruzen's favoured candidate for a long time) is a testament not only to the Third's faith in Minato, but also his faith in Jiraiya raising a shinobi, and a man, of unparalled aptitude and morals.
Jiraiya wandered all the Elemental Countries. He was never accused of turning his back on the village, as his teammate Tsunade. He was the only Leaf shinobi with knowledge of Akatsuki when they first revealed themselves, and was later chosen to be the one to infiltrate their stronghold in Amegakure. This all points in one direction: Jiraiya was a spy. Perhaps the undisputed greatest one in the village of Konoha.
Supporting evidence is found in many places, not least in his arsenal of techniques. Jiraiya posesses the LARGEST amount of quality stealth/infiltration/interrogation techniques of any shinobi shown in the series.
The Canopy Barrier, used to great effect against Pain's Chameleon Summon, is capable of detecting any motion in a large area even when the user himself is moving. I surely need not describe how this would be useful for stealth, infiltration and detection.
The Gourd Toad Prison, a handy container for any valuable object or person.
The Hiding in a Toad Technique, capable of infiltrating underwater areas, with the ability to avoid sensory techniques even of such magnitute as Pain's sensory rain.
The Summon: Toad Shop, an excellent trap or shelter.
The Toad Shadow Domination Technique, capable of as much control as any Nara clan jutsu, but is performed without its wielder being visible. And excellent technique for entering hidden areas, impersonation, stealing and much more.
The Transparent Escape, an actual invisibility jutsu.
The Forced Frog Transformation, a psychologically devastating interrogation technique of proven effectiveness.
Jiraiya's espionage techniques:
http://naruto.wikia.com/wiki/Barrier...thod_Formation
http://naruto.wikia.com/wiki/Barrier:_Toad_Gourd_Prison
http://naruto.wikia.com/wiki/Hiding_in_a_Toad_Technique
http://naruto.wikia.com/wiki/Summoni...Shop_Technique
http://naruto.wikia.com/wiki/Transpa...cape_Technique
http://naruto.wikia.com/wiki/Turning...Frog_Technique
http://naruto.wikia.com/wiki/Toad_Fl...tion_Technique
But how could Jiraiya be a spy? He is loud, loutish, genial, perverted, brightly and distinctively dressed, perpetually dramatic.
Answer: What happens when he ISN'T any of those things?
Jiraiya is a master of deception and rarely if ever underestimates his opponent, or caught off-guard. (The Pain fight is a bit of a special case and I'll get to it in later posts.) He's capable of fooling even intelligent opponents in the midst of combat.
Here seen in his battle with Pain:
Orochimaru, who has a proven record of underestimating his opponents (Itachi, Sasuke), also falls for Jiraiya's duplicity, even after YEARS of close association:
Jiraiya has the single greatest feat of memory (and possibly willpower) in the ENTIRE series:
Here, while on the brink of death (after having FORCED his heart to start beating again) he writes a cipher based on words and pages in one of his books. Not even his personal favorite (that honor goes to The Tale of a Gutsy Ninja:
It's an autobiography, describing Jiraiya's lifelong search for peace. Minato, who knew him, believes in it so much and thinks it so close to his teacher's heart that he names his son after the main character.)
But, the cipher based on words and pages requires knowledge of a sort Qu'ran scholars, for instance, require years or even DECADES to achieve with their chosen work. Jiraiya didn't even like his book that much, yet he remembers EVERY WORD. Even while having DIED, if death is defined as the cessation of the heart.
If there is a battle of wits between these two, do not expect Orochimaru to take the victory. He already underestimates Jiraiya and THIS:
Tends to happen to people who underestimate Jiraiya.