When Itachi and Kisame squared up against Jiraiya, the two were sent packing. But why did Itachi run from Jiraiya?
Itachi had to run from Jiraiya because of the Toad Mouth Trap ninja art. Jiraiya’s jutsu summoned a rock-dwelling toad from Mount Myoboku that placed Itachi inside its stomach, its flesh grabbing and restraining Itachi.
This is the first time we’ve seen the Amaterasu in use, as Itachi used the eternal flames to burn a hole in the Toad’s stomach and escape.
Chapter Behind Why Itachi Ran From Jiraiya
In chapter #148, Jiraiya used the Toad Mouth Trap ninja art in an attempt to restrain Itachi and Kisame. The duo proved they couldn’t be taken down in a straight-up fight, so Jiraiya hoped to slow them down and hopefully imprison them in the toad’s stomach.
I’ve just performed the ninja art of Gamaguchi Shibari! Toad Mouth Trap! You’ve just been swallowed by the rock-dwelling giant toad of Mount Myoboku, welcome my friends, to the belly of the beast.
Jiraiya describing the technique | Chapter #148
The giant toad’s stomach began to swallow Kisame and Itachi, pulling at their legs and weapons and fusing them to the walls. Kisame rips his sword, the Samehada, out from the consuming flesh and flees with Itachi through the stomach.
Jiraya tells Naruto to stay put, explaining that no one has ever successfully escaped from the Toad Mouth Trap before.
In an act of desperation, Itachi uses his Amaterasu to burn a hole through part of the flesh. The Amaterasu is a Sharingan technique that creates eternal black flames around its target, forever scorching until the target is fully incinerated.
“They’re powerful enough to burst through this wall.”
Jiraiya after witnessing the Amaterasu | Chapter #148
After the two successfully escape, Kisame asks Itachi why they needed to retreat using a Sharingan power.
There’s no need to be impatient… none. Besides which, I must also… rest my body in one place for the foreseeable future. For not only Tsukuyomi, the nightmare realm… but I was forced to use the Amaterasu as well.
Itachi talking to Kisame | Chapter #148
Jiraiya stops Naruto from touching the Amaterasu flames, thinking to himself as to what this newly witnessed technique could be.
“How did they get out? And what are these black flames? The Rock Toad normally spews fire himself, so for his naturally flameproof innards to get charred…”
Jiraiya talking about Amaterasu | Chapter #148
So there’s the answer. Why did Itachi run from Jiraiya? The Toad Mouth Trap was close to capturing Itachi, so he needed to use his Amaterasu and escape.