This fucking hellsite ATE MY POST so here my second attempt to respond sans screaming and hair pulling lol!
There are so many different answers to this question! I think it largely depends on *which* incarnation of Itachi a given shipper prefers: pre-reveal villain!Itachi, post-reveal martyr, non-massacre AU, canon divergent, Akatsuki!Itachi, double agent…the list goes on forever, and this ship is older than you’d think.
That said, I personally am in it for the slow burn enemies-to-lovers potential. With gratuitous use of forced proximity causing humanization. And leading to tentative friendship and confused attraction. The BEST UST mmph!
Much of the fandom seems to rely on a cold, somewhat robotic characterization of Itachi to be considered IC, which sells him short, imo. There’s so much more potential!
Some headcanons of their similarities: both intellectuals, natural strategists and planners; loyal to Konoha to a fault (bonus points when played as a genuine flaw); deeply concerned with ethics and Doing The Right Thing (tho Itachi always gets it wrong the first time round like a true extremist); both care about their loved ones more than virtually anything else.
I believe Itachi tempers some of Sakura’s hotheaded recklessness, while Sakura brings out some of Itachi’s repressed passion. I see them as deeply compatible teammates who make each other better. I come back to this ship time and time again because of my perception of their fundamental equality and respect for each other. *fans self furiously*
For fics, I confess I am a Fandom Crone, so I’ve only got older ones. Since I prefer enemies-to-lovers, these tend to put political conflicts between them at the center:
These two are super fun to write!
If you decide to do some reading please come back and tell us if you’re into it! Always thrilled to see more ItaSaku love in the world. It doesn’t get as much attention as other ships but there’s so much good energy there ;_;
EDIT: Imma tag my fav KS shipper @neonanything because after all these years of friendship (and neighborship!) it’s time you understood this side of me, too, if you ever dare come back to tumblr dot com!!!!