Kaien Connection
Indeed, Rukia recognized his striking similarities with Shiba Kaien (note the black hair in the shaded flashback segment), a person she deeply loved and admired. <<< Read from RIGHT to LEFT <<<

Chapter 117
Kuchiki Byakuya recognized this too... <<< Read from RIGHT to LEFT <<<

Chapter 56
So did Ukitake Juushirou, Captain of the 13th Division and Kaien's superior when he was alive. <<< Read from RIGHT to LEFT <<<

Chapter 117
But Byakuya did not echo Rukia and Ukitake's sentiments for the Shiba family. <<< Read from RIGHT to LEFT <<<

Chapter 116
But why the grudge? And who was Shiba Kaien anyway? He was the Liutenant/Vice-Captain of Rukia's own 13th division, and the older brother of Ganju and Kuukaku. Kaien did not share the Shinigami reverence for code, structure, and regulation... something Byakuya held sacred. <<< Read from RIGHT to LEFT <<<

Chapter 134
When Byakuya revealed that his reasons for being content to not interfere with Rukia's fate, and even willingness to execute her death sentence himself out of respect for the Soul Society's (the Shinigami's world) code, Ichigo indignantly protested that motivation. This once again reminded Byakuya of Ichigo's unmistakable parallels with Kaien (note the black hair in the flashback segments again), who was not afraid to challenge authority and tradition. <<< Read from RIGHT to LEFT <<<

Chapter 167
Kaien was the world to Rukia. He looked out for her and was perhaps the only one who made her feel like a normal person instead of a spoiled brat who got pushed ahead without passing the entrance exams or a feared/revered noble. It was no wonder that she developed a profound infatuation with him, but alas he was married. "As long as you're in my division, I will stand by you even if I die" he had told her, and die he did... But before we explore the circumstances of his demise, let us observe another one of Ichigo's parallels.

We have already seen that Ichigo looks and acts like Kaien, but he uses Kaien's exact phrase, as well: "even if I/you die." Coincidence? I think not. It is obvious that Ichigo is obsessed with protecting Rukia, but could his overwhelming determination to do so have originated well before he was born?

<<< Read from RIGHT to LEFT <<<

Chapter 134, 152
It is relevant to note that the United States manga release by Viz Media translated Kaien's "I will stand by you even if I die" as "I'm your friend for life." This was probably done for sake of superficial coherence, but it loses a potentially important vow between Kaien and Rukia that transcends death. If you read the Japanese chapter 134, the phrase is "Ore wa shin de mo omee no mikata da" - "I am your friend/ally even if I die." Likewise, Ichigo's phrase in the Japanese chapter 152 is "Shin de mo hanasuna yo" - "Don't let go even if you die."
Kaien's death was a tragic event that scarred Rukia for life, and one she dwelled on and flashbacked to relatively often. The first time she did so in the series was when Ichigo told her to let him fight the Hollow that killed his mother without her help. Those words still tore her apart inside with guilt and anguish, for he was reenacting the circumstances of Kaien's death. <<< Read from RIGHT to LEFT <<<

Chapter 23
When Kaien's wife and her entire squadron were wiped out by a Hollow, he disregarded Soul Society's standard procedure of researching the Hollow's capabilities and then putting together an appropriate task force. He decided to go after it alone based purely on the knowledge of its location. The Captain of the 13th division, Ukitake Jyuushiro, and Rukia accompanied him to the lair, but Kaien insisted on fighting the Hollow by himself and Jyuushiro obliged. The Hollow shattered his zanpaku-tou and possessed his body, turning him into a monster. Rukia was forced to kill him and he died in her arms, grateful for the opportunity to fight alone. <<< Read from RIGHT to LEFT <<<

Chapters 133, 135, 136
Incidentally, this also spawned Shiba Ganju's hatred of Shinigami, because it amounted to Rukia killing his brother. I repeat, KAIEN is GANJU'S BROTHER and RUKIA KILLED HIM. Let that sink in.
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