The Too Distant Elder Brother

Having Fugaku at his side for his very first day at the Academy filled Sasuke with pride. That joy soured under the piled-on hopes of his father, his teachers, and even his peers, all of them measuring him against Itachi's record. He poured himself into the effort and earned some early praise from Fugaku, yet the demands only mounted. Itachi, for his part, was fraying beneath the duties he was expected to shoulder as the Uchiha clan's future. He once guessed that Sasuke resented him, and though Sasuke tried to assure him otherwise, Itachi maintained that an elder brother's purpose was to stand as a wall for the younger to overcome.

Sasuke starts at the Academy with Fugaku present, but the constant comparisons to Itachi wear him down despite his hard work. Itachi shows the strain of his own expected role in the clan, voices the suspicion that Sasuke bears him ill will, and frames his job as being an obstacle for his brother to surpass.

Part of the Sasuke Recovery Mission arc, this is chapter 221 in the twenty-fifth volume, titled Out of Reach in the Viz edition. It is a flashback chapter examining the early relationship between Sasuke and Itachi.