Sai

Sai has short, straight black hair and dark eyes set against strikingly pale, almost translucent skin, a look many observe as resembling Sasuke Uchiha. During his Root days he wore a cropped grey-and-black jacket fastened with red straps over a high-collared shirt that left his midriff bare, along with gloves cut away at the thumb and index finger to free his drawing hand. A blunted tanto rides across his back, and he keeps a small pack of brushes, ink, and scrolls close by. A cursed seal once marked the underside of his tongue, vanishing only when his master died. As the years passed his clothing grew more concealing, his hair lengthened before being cut into the short ponytail favoured by the Yamanaka, and the scroll he hauls for his sealing techniques kept growing larger.

When Sai first appears he is all but hollow, his emotions buried so thoroughly by Root conditioning that he hides behind a blank stare or a practised, empty smile. That upbringing left him loyal to whoever gives the orders and blind to how the ties between people move them, which is why Naruto's willingness to risk everything for a traitor genuinely baffles him. Socially clumsy, he wounds people by blurting whatever crosses his mind, once dubbing Sakura "Ugly" and then overcorrecting by calling Ino gorgeous when he meant the opposite. Time with Team Kakashi gradually thaws him. He comes to prize the bond between Naruto and Sasuke, begins recalling his lost brother Shin, and learns to smile for real while chasing as many friendships as he can. By the great war he grasps camaraderie completely, and in the years afterward he opens fully to love, marrying Ino, raising their son Inojin, and rejecting the teachings of Root as sincere yet misguided.

Orphaned young, Sai was taken into Root, the covert wing of the Anbu run by Danzo Shimura, and stripped of name, attachments, and personality; even "Sai" was merely a label assigned for his placement on Team Kakashi. His one surviving spark was a love of drawing, encouraged by an older recruit, Shin, whom he came to regard as a brother before illness took him. Sai channels that art into combat through his Super Beast Imitating Drawing, bringing inked birds, beasts, and clones to life, and his Root schooling also gave him sealing techniques able to trap enemies inside a painting.

Danzo slipped Sai onto Team Kakashi with secret orders tied to Sasuke Uchiha, but exposure to Naruto's loyalty cracked his conditioning and he chose to protect that bond rather than betray it. He stayed with the team afterward, reading up on friendship in a bid to build his own. When Danzo seized the office of Hokage, Sai was set to watch Naruto, yet he broke ranks enough to explain to Sakura the depth of Naruto's feelings for her. During the Fourth Shinobi World War he served in the front-line divisions, sealing away foes such as the resurrected Swordsmen of the Mist and being forced to battle a reincarnated Shin, whose spirit found peace once Sai's long-unfinished picture book was completed.

In the years that followed Sai rose to lead the Anbu, married Ino and took the Yamanaka name, and helped raise their son Inojin while working beside her at the family flower shop. Through the Boruto era he repeatedly turned his skills to defending the village, digging into Root's dark legacy and the schemes of the Kara organisation.