No, actually, Itachi and Jiraiya died on different dates, times, and circumstances in the Naruto series.

We’re going to look at how each of these characters died and by whose hands they died because in their deaths, a very crucial part in the growth of certain individuals who we believed were part of the main storyline and that growth was a key factor.

The Circumstances of Jiraiya’s Death

In continuing the timeline as well as the atrocities, we’re going to scratch one by one the circumstances of Jariah’s death. In the final mission, Jariah decides to go on a covert mission to the hidden brain village, where he tries to investigate all he can about the leader of the Akatsuki, Pain.

This is a fatal mission as he learns that Pain is none other than the former student, Nagato, possessing six paths of Pain.

The Final Mission

This mission was one of the most crucial missions he could have faced because he was probably  Going to face, and indeed he did face, one of his former students, Nagato, who, along that time, was now considered as Pain due to the power he had, that was called the six paths of Pain,

Underestimation of the Enemy

Jiraiya was an intellectual ninja whose role was to collect information crucial to the village’s safety. Jiraiya’s visit to Hidden Brain village was to collect important information about the leader of Akatsuki, Pain.

But because he underestimated his opponent, and he did not knowingly that Pain possessed a unique ability of the six parts of Pain, which proved to be more formidable than Jiraiya thought. This miscalculation led him to his inability to escape from his foes, eventually getting killed.

Lack of Support and Isolation

Normally, during covert missions, Shinobis tend to travel in groups to provide support to each other, as well as manage to sustain any immediate medical attention and technical support that is needed. However, due to Jariah’s soft heart, he avoided involving others in serious, risky missions like this.

But that was the backup he needed at that time due to the mission’s escalation. Also, his biggest mistake was he underestimated the enemy and an unknown area. So, the isolation made it impossible for him to escape and hopefully survive, which made his decision under demise to undertake this mission alone.

The Circumstances of Itachi’s Death

The Brotherly Duel

We all know that Itachi eventually fights against his younger brother, Sasuke, who intends to finally get revenge on his brother for massacring not only the entire Uchiha clan but also their parents.

Itachi does go into this immense battle with Sasuke. However, Itachi was suffering from a terminal illness about which nobody knew. So, when he was fighting with Sasuke, he had already become weak due to the terminal illness.

Health Deterioration

Now.  If we are to look at  Itachi Uchiha, we know him to be one of the best  Shotgun users in the Uchiha clan. Therefore, he was among the greatest ninjas of all time in the Shinobi world.

But during his fight with Sasuke, it seemed like he was holding back, and indeed, he was holding back because he was suffering from a terminal illness. Therefore his weakened body forced him to have reduced stamina and physicality, making him fight for a shorter period.

Strategic Sacrifice

Itachi had already planned out that he would die at the hands of Sasuke with the hopes that by Sasuke defeating him, he would eventually turn tails and decide to head back to the village. So, it was Itachi’s strategic sacrifice to protect his brother and the village.

Timeframe and Narrative Importance

Chronological Separation

The deaths of both Jiraiya and Itachi were major events throughout the series,  causing both characters, Naruto and Sasuke, to change and grow maturely.

As for Naruto, with Jiraiya’s death, he was forced to learn the Senjutsu, also known as the sage mode, to learn the power of using natural energy.

For Sasuke, it allowed him to change from his darker path of revenge and vengeance to uncovering the truths about the hidden leaf village and the Uchiha clan.

Emotional and Thematic Resonance

Now we have seen that both deaths were a major key part in developing the series’ key characters to drive them forward. Because when we look at Itachi’s death shows us the complex narrative narration of how sacrifices and responsibilities are handled in the ninja world, as well as Jiraiya’s death teaching maturity.

Conclusion

Therefore,  we can safely conclude that Itachi and Jiraiya died in different circumstances and at different times in the series, but their deaths played a crucial part in our key main characters, Naruto and Sasuke, evolving in their own way.