Jiraiya, a legendary Sannin in Naruto, knew  Itachi as one of the greatest ninjas known in the Shinobi world. He was aware of Itachi, I didn’t, we don’t, we want to find out to what extent he knew about Itachi.

However, it is impossible to say if Jiraiya actually knew the real motives behind Itachi’s actions, especially the Uchiha clan massacre. Because he considered Itachi to be a formidable opponent after Itachi and Kisame infiltrated the Konoha village.

1. Jiraiya’s Awareness of Itachi

Jiraiya was well-integrated with the village’s intelligence network, which allowed him to get information about all the ninja activities and profiles. In his ninja profile, Itachi was also included, an exceptionally talented ninja of the Shinobi world.

Moreover, Itachi, part of Anbu, became its captain very young. And, so due to his amazing capabilities, Itachi became a key interest to Jiraiya. However, despite having this much information, Jiraiya never knew about Itachi’s real motives behind his actions.

Itachi’s Defection and Subsequent Activities

Following Itachi’s defection from Konoha and his affiliation with Akatsuki made Jiraiya cautious about Itachi. Moreover, Itachi’s shift from a talented Anbu captain to joining a criminal group posed a big threat to the village.

That’s why Jiraiya started staying more alert for Itachi’s actions due to his commitment to protecting Konoha. For this, Jiraiya would always have a constant watch on Itachi’s interactions with Akatsuki members and the missions in which he participated.

Therefore, at the time when Itachi and one of the Akatsuki members, Kisame, infiltrated the Konoha district, Jiraiya put more of his alertness on the movement of Itachi with the Akatsuki rather than paying attention to other commitments he had to the Hidden Leaf.

Implications for Konoha’s Security

Knowing that Itachi was an Anbu Black Ops captain, Jiraiya knew they had to be extra alert regarding the village’s security because they knew that Itachi possessed many profound abilities and strategic insight.

While monitoring Itachi, Jiraiya would track his direct threats and pierce down his potential motives and the Akatsuki strategy. This surveillance was crucial for Jiraiya to carry out for the village’s safety.

Also he had to make the village prepared against all the possible threats that Itachi would bring through his actions.

Moreover,  by infiltrating Konoha, Itachi made himself a rather serious threat to Konoha, which brought Jiraiya’s attention to Itachi as part of the Akatsuki strategic plans, rather than other means of stake missions that Itachi had to go through to protect the village.

2. Jiraiya’s Perception of Itachi’s Actions

It may seem like Jiraiya’s understanding of Itachi was  More on him being the Akatsuki member rather than his missions to annihilate the Uchiha clan.

Also, Jiraiya didn’t know about the potential civil wars that the Uchiha clan was planning to wage, which led to their destruction by Itachi.

And only a few individuals from the higher-ups were left.  This main story of Itachi’s great sacrifices was kept confidential and was known only to a few people within the higher echelons of Konoha’s leadership, like Danzo, the third Hokage.

Later, Tobi reveals this information to Sasuke and eventually finds out through Tobu after he has already attained his revenge against his brother.

3. The Impact on Jiraiya’s Actions

Jiraiya was an intelligence network ninja, gathering information for the sake of hidden myths, strategic planning, and threats like the Akatsuki. His main motive was gathering information about Akatsuki’s plans and members, including Itachi.

His focus had always been more on the organization as a whole rather than Itachi individually, as understanding Itachi’s capabilities was very important for Jiraiya.

4. Jiraiya’s Role as a Mentor

As Jiraiya was Naruto’s mentor, his knowledge about Itachi influenced how he would train Naruto because he had to ensure that Naruto would be ready for any future threats, especially from Akatsuki. Jiraiya’s training helped Naruto equip skills to help him fight the Akatsuki.

Conclusion

So,  When you look at all these features, we can see that Jiraya was aware of Itachi,  but he was clueless about the great sacrifices Itachi had to go through and the burdens he had to take on.