"Itachi, do you regret it?"
Itachi's resolute expression froze the moment he heard those words.
Clearly, Naruto's question had struck directly at his pain—the issue he was most sensitive about and least willing to admit. In a daze, Itachi seemed to recall what his father, Uchiha Fugaku, had said before his death—
"Itachi, was this your choice? Your father is proud of you. I hope you won't regret your choice in the future..."
Will I regret my choice?
Itachi began to question himself.
At first, when that choice had been placed before him, Itachi had loved the village too deeply. He could only choose, and so he chose to let Sasuke live.
At that time, Itachi had not truly regretted it, because he had had no choice. If he had not chosen, no one in the Uchiha clan, including Sasuke, would have survived.
Sasuke could be considered the reward he had obtained for slaughtering the Uchiha with his own hands.
Yet during the time he later spent infiltrating Akatsuki, through mission after mission, he saw more of the world, witnessed more things, and came to understand more.
Only then did regret slowly begin to grow within Itachi.
As the seeds of regret took root, Itachi often could not sleep. Whenever he did fall asleep, he would first be dragged into nightmares, then jolted awake by them, left with no choice but to stand beneath streetlights and wait for dawn.
Only at such times did Itachi begin to reflect and remember. If that same choice were placed before him again, would he still choose it?
Itachi was not sure whether he would make a different choice.
But without question, no matter what choice he made, he would regret it.
Perhaps what he regretted most was that he could no longer interact