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Before Shin's death, Sai created a picture book that would depict all the opponents they faced and illustrate the feelings that they shared for each other.
When Shin, an older Root member, discovered Sai's drawing ability, he encouraged Sai's talent and they became very close.
Over time, Sai came to think of Shin as an older brother and looked up to him.
He often showcases this confusion after thinking about why Naruto would go so far to save Sasuke, a traitor, even though Naruto had not been ordered to do so.
Sai's social awkwardness tends to get people angry, because he often speaks without considering his words and their effects on people.
Some time after the loss of Shin, Sai forgot that this was his intention, and the picture book was left unfinished, though he could never bring it upon himself to discard the book.
During his time in Root, Sai was ordered to eliminate a large number of individuals that posed a threat against Konoha.
This was due to his inability to realise the difference between a rude statement and a true statement.
Sai had read somewhere in a book that giving somebody a nickname would bring you closer to that person and develop your friendship, this resulted in Sai hurting Sakura Haruno's feelings, because he called her "ugly", stating the first true character trait that came to his mind.
Unfortunately, the final step in Root training called for the two to fight to the death to eradicate all remaining emotions.
Before that happened, however, Shin died of an unnamed illness and Sai's Root training suppressed most of the memories he had of him.
See if you can knock down your opponent before he outpunches you.