Top 10 Most Heart-Breaking Moments in Bleach
1 being the most heartbreaking
10) Nnoitra flashbacking on his life and stating the pain others make him feel is like "stomping on a open wound", then getting cut down, he slowly falls, and catches the eye of Neliel, and dies. 9) Byakuya slammed into a wall covered in his own blood, thinking on how failed he Rukia and Renji, with his blade shattered. 8) Ichigo losing his powers and watching as Rukia, the one who gave him so much, fades away.
7) Unohana dying in Kenpachi's arms and thinking he's the only man she ever cared about. 6) Soul Society being decimated by Quincy and then they receive a message that Ichigo is on his way and they gain a great resolve to battle, but Ichigo gets trapped and can't get to them in time. And he listens as some of his comrades are brutally murdered.
5) Starrk realizing that Lilynette (who was his only true friend) has disappeared - being killed by Shunsui - and that he is all alone again. Then as he dies he thinks back on how he gained friends by being with the Espada (but we know they weren't really his friends and that's the worst part)
4) Gin dying a criminal without his true intentions ever being revealed, while Rangiku cries over his body.
3) Ulquiorra reaching out his hand to Orihime, but before she can grab onto it, his body turns to ash and he learns what a heart is. And then Ichigo screaming "this is no way to win" at his ashes.
2) Ichigo crying as Ginjo betrays him and steals his fullbring, and Ichigo knowing all his friends have been turned by Tsukishima, and then turns still crying believing his dad has just stabbed him with a sword. 1) Never knowing what freaking happened to freaking Izuru Kira.And wondering if Grimmjow is really coming back! Like WTF TITE!