My four chosen disciples.
Because of Yoruichi Shihōin, Shadow taught Byakuya Kuchiki Swordsmanship. However, Byakuya Kuchiki from 110 years ago did not meet Shadow's standards, so Shadow would not acknowledge him as his disciple.
When the Visored defected and the story began, Byakuya Kuchiki and Renji Abarai went to the World of the Living to capture Rukia Kuchiki. Even then, though Byakuya Kuchiki looked remarkably like him, he still did not meet Shadow's standards.
It was only after Aizen left the Soul Society, when Byakuya Kuchiki said "Sorry" to Rukia Kuchiki, that he finally qualified.
Kenpachi Zaraki had a personality that was the complete opposite of Shadow's, and he was also the one Shadow found most satisfying. In his previous life, Shadow had grown up among wolves. He could be called a standard humanoid beast. However, while wandering the Shinobi World, Shadow learned the art of assassination and how to hide his emotions. As time passed, fewer and fewer people could bring out Shadow's ferocity.
It was precisely because Kenpachi Zaraki was so pure that Shadow, burdened by regret and unable to let go of the past, envied his free-spirited nature.
Gin Ichimaru inherited the Assassination Path. The way his personality resembled Shadow's most was that, no matter what happened—whether pain or sorrow—he would never tell anyone. He hid it in his heart and silently endured it. For those he wanted to protect, no price was too great.
Ganju Shiba inherited the path of Ninjutsu. He fit Shadow's standards even less than Byakuya Kuchiki; Shadow had never even considered him. But when it came to standing by his principles, he was undoubtedly much stronger than Byakuya Kuchiki. Actually, sometimes he was pretty adorable too!
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