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Itachi’s Lament: Poor Jack

Summary:

But I never intended all this madness, never
And nobody really understood, well how could they?
That all I ever wanted was to bring them something great
Why does nothing ever turn out like it should?

-

Or:
after Sasuke tries to kill Itachi for the first time, he is saved by Naruto and Jiraiya. It gets Itachi thinking.

Notes:

wow this took a while to make and is embarrassingly short but maybe the next part will take less time

Reminder that each part of this series can be read in any order for a different perspective on the overall story, so feel free to skip around

(Slight formatting update made on 07/25/2025)

(See the end of the work for more notes.)

Work Text:

There was no fire—that would draw too much attention. No, it was just the dark, soulless night. It peered at Itachi enough to make his bones chill beneath the surface.

 

His partner, lying inside the cave behind him and using his black-and-red Akatsuki robe as a blanket, snored so loudly it was a wonder that each great Kage wasn't inspecting their location. The Uchiha took a deep, steadying breath. His hands found his temples, rubbing deftly at the skin there to relieve some of the tension.

 

Itachi's eyes slowly drifted heavenward, his gaze instinctively fluttering toward the full moon of the night. The peaceful breeze somehow felt punishing against his skin. The mission had already taken a lot out of him. Seeing Sasuke again after all of these years…

 

The fierce red of his Sharingan pierced into Kakashi—around his skin, weaving in and out of his very organs. The Hatake was nailed to a cross, his body limp and shivering.

 

He lifted the sword in his hand and drove it into the man's stomach. He ignored the heave of pain, the way his body shivered after the repeated abuse.

 

Then, in the blink of an eye, it started again. And again. And again.

 

It was challenging to remember the seemingly distant time when Kakashi was something of a friend, or perhaps a superior. Back then, back when everything was so much simpler, the man seemed so powerful. So... strong. His existence was simply unattainable. Graduation at five—those numbers put Itachi to shame.

 

Was he just out of shape? Itachi's gaze shifted to his hands. No. Even if Kakashi wasn't an active ANBU, he still engaged in plenty of dangerous missions as a Jōnin.

 

The tomoe in Sasuke's bleeding eyes spun wildly as he tried to take in the scene around him. Itachi—killing them all. He was killing them all. The boy did his best not to scream.

 

Genjutsu. It's just a Genjutsu. He had screamed those words at the top of his lungs for just a bit too long. Too desperately for someone too weak.

 

It was all too familiar. The same images haunted Sasuke's dreams; the same memories gutted him open every time he attempted to enter his old compound.

 

The second the last body fell limp on the dirt floor, they would start from the beginning once more. Sasuke reached up and tried to rip out all of his hair.

 

Itachi ran his hands down his face before slumping over and letting out a large, dense sigh. Fuck.

 

Briefly, his hands twitched. Some habitual instinct, begging him to reach over and grab a kunai to shove into Kisame's snoring gaw, then into his own eyes. He could take out the mangekyo and then run, living out the rest of his days in a small, civilian settlement. He'd like a peaceful life of that sort.

 

He sat on his hands.

 

Itachi's gaze drifted up to the moon as he let out a dutiful sigh. He stood and strolled over to his partner's side, tapping his shoulder twice to wake him up. When the fish-like man began to stir, Itachi spoke, "It's time for your shift."

 

"Finally getting some shut-eye, Uchiha?" Kisame chuckled lazily as he sat up, rubbing the sleep away from his eyes briefly. Itachi ignored the comment and moved to a comfortable ledge. Unfortunately, despite being an Uchiha, he was a mere human and therefore required some sleep every once in a while.

 

Once Kisame had stood to gaze out of the cave with crossed arms, the tired Uchiha began his breathing exercises. He fell asleep in eight minutes.

 

Sasuke's cute, kiddish smile he'd shine at Itachi whenever they finally got to spend time together. It beamed at him. That face, he swore to his parents, is one he would protect. His brother would always be smiling. Itachi would protect him, no matter the cost.

 

In a flash, his expression shifted, and he was staring down at Itachi in a motel hallway. Pure, unbridled rage in his gaze, and lightning sparking at the tips of his fingers. He charged at Itachi with a scream, a promise of murder.

 

Heartless Itachi grabbed his dear, smiling brother by the neck and slammed him into the wall. He squeezed the too-young neck between his fingers with might far too strong—it had to, at least, appear real—for too long. He wouldn't have even done it if he hadn't sensed the Sannin nearby.

 

When Jiraiya came with the jinchūriki boy in tow, he changed the walls into the inside of a frog. Sasuke’s limp, nearly lifeless body was sucked into the wall. Itachi’s heart slammed in his chest the second he recognized the tuff of white hair. They fled. They wouldn’t have made it out alive if Itachi didn’t use amaterasu at the last second.

 

Sasuke was safe, just as Itachi had promised. Safe from himself. His brother.

 

Was he?

 

Even when Itachi was miles away, sleeping in a faraway cave, Sasuke wasn’t safe from him. The rage in his eyes, the fleeting hatred he felt, it was all Itachi’s doing. It would persist until one of them died.

 

Itachi looked down at his hands—it was a strange, fuzzy feeling that made his head spin—and he suddenly felt a face flash through his vision. Danzo. Because if there was any threat to Sasuke at all, it was Danzo, who couldn't do anything too directly, but...

 

ROOT members of ANBU don't leave. They live in secrecy and die in more than that. Traumatized, young, power-hungry? More like eye candy for that traitor. Red-hot rage filled the Uchiha's system, a type of rage he hadn't felt in years.

 

"Sun's comin' up." Came a rough mumble along with two taps on his shoulder. Itachi blinked awake, then looked up at his... teammate. Partner. Friend?

 

While they locked eyes, Itachi flickered on his mangekyo. Kisame fell to the ground. His breath was heavy as he was pulled into a peaceful genjutsu of meadows and flowers.

 

He had only one option. Itachi Uchiha was a tool and a killing machinehe must do what he does best.

Notes:

I hope you guys liked it!! Let me know if there’s any problems. As always, all comments and kudos are appreciated ❤️❤️

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