I find that when it comes to Itachi there’s two kind of extremes that people tend to fall under/towards. It seems people either see him as having done nothing wrong and dismiss the severity of the consequences of his actions after the reveal that he was working for Konoha/to protect Sasuke, and others see him as basically a person who had 100% agency over his actions, made terrible decisions, and was handled irresponsibly by the series and Kishimoto. While I’m not the latter and disagree with most of those points, my stance is closer to it than it is to the former. This means I end up seeing/reading stuff in that vein a lot, and there’s one point that I think tends to be a bit missing from the conversation. It came up while I was talking to @someone-who-is-there about some points on this thread.
When we talk about Itachi and his actions regarding the Uchiha clan, it is necessary to take into account the context of his situation with Danzo, who heavily manipulated Itachi and had a major role in Itachi’s final decision. This got long, so it’s under a cut.
Tag: itachi
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Statement 1: Itachi was taking medicine for years for his illness, all to keep himself alive.
Statement 2: Obito was acutely aware of this. Including the length of time Itachi was taking medicine, and that his illness was eating him from the inside out.
Initial conclusion: Kisame was reporting Itachi’s status back to Obito. Given Kisame was one of the first members of Obito’s Akatsuki, he is assigned to watch over Itachi.
Problem: Kisame doesn’t like backstabbers, or people who withhold information, as evidenced by his backstory.
Secondary conclusion: Obito, being the one who originally recruited Itachi into Akatsuki to begin with, regularly had meetings with him. Obito was his supplier of medicine, knowing Itachi was a problem who would take care of himself at the “right time.” Kisame was still assigned to watch over Itachi, but more to compliment his abilities and keep him safe, rather than reporting back to Obito.
Thoughts welcome.
addendum: The Jinraiden novel specifically mentions that Itachi traveled to it to retrieve his medicine. This village is his supplier.
Tertiary conclusion by @antatchaburu: Zetsu is spying on Itachi and reporting back to obito.
Problem: Zetsu had no idea Itachi was sick during his fight with Sasuke.
final, but not permanent or serious conclusion: Itachi is silly and makes things too complicated. Itachi why are you like this. ]]

Newly branded, she comes to the Hokage to request assistance in ending the practice, or finding a solution that brings equality to all Hyuuga.
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[[ :3 for @pacifistuchiha ]]

[[ Have my sketches yo.
None of them are to scale, or else I’d be worried. ]]

[[ New drawing habit: start something on impulse and finish it asap. ]]