Jiraiya realized that Itachi used an illusory technique to separate him from Naruto and raced back to the hotel in time to find them. Itachi confirms that the Akasuki wants Naruto. As Jiraiya prepares to attack, Sasuke tells him not to interfere. He will be the one to kill his brother. Jiraiya respects Sasuke's wishes, but it doesn't take much for Itachi to mess Sasuke up pretty badly. He breaks his arm and then pounds him again and again. Finally, he pulls him against the wall and calls him weak because he lacks hatred. He again uses Mangekyou Sharingan to force Sasuke to relive that day for the next 24 hours.
Naruto can't watch his teammate suffer anymore and runs at Itachi. Jiraiya uses Ninpou Gamaguchi Shibari (Frog Mouth Trap) to pull Sasuke away from Itachi and capture the two Atasuki. His technique turns the walls of the hotel into a frog's stomach. But Itachi is able to use a strange black flame to burn through Jiraiya's technique and they escape.
Jiraiya is fascinated that Itachi knew how to break his technique. He then uses Fuuinjutsu Fuukahouin (Sealing Technique, Fire Suppressor) to contain the black flames and store them in a scroll.
Once the danger is gone, Gai shows up to tend to Sasuke while Jiraiya and Naruto ponder their next move. Naruto wants to go after Itachi, but Jiraiya informs him that he's much too weak. Gai mentions that Itachi was able to use a similar technique on Kakashi earlier and now Kakashi's unconscious. He hopes they find Tsunade, the medical specialist. The women with the word gambler on her back.