Hugest regret in Naruto?

[Guardian of the Rain]

Which shinobi possesses the biggest regret ever in the Narutoverse? Examples:
-Obito giving Kakashi his eye, now Kakashi uses it against him.
-Madara trusting Nagato to revive him with Rinne Tensei.
-Kakashi not doing his best to keep Sasuke away from the darkness.
-Sakura treating Naruto like shit earlier in the series, she probably wants him now.

 

[R4mbl3]

Kakashi not stopping Sasuke.

 

[sG Taka]

The character that holds the hugest regret is Neji, for being Hinata's cousin.

 

[MacMiller]

Naruto kissing Sasuke.

 

[Kyuubibomb]

definitely Kakashi not being able to stop Sasuke

 

[Itachi15]

Itachi for not trusting in sasuke

 

[~Dream~]

Starting to read the Manga.

 

[Delta]

hugest isnt a word btw and id say kakashi not stopping sasuke

 

[CurseSealofEarth]

Minato/Kushina for having to leave their only child alone for his entire life.

 

[~Sky~]

I think it's Jiraiya, because he had several regrets.

Not saving his friend
Not saving his student
Not saving his master
Not getting the woman of his dreams
Not stopping the Akatsuki

 

[Guardian of the Rain]

definitely Kakashi not being able to stop Sasuke

He was able to stop Sasuke, but he barely tried. There was much more Kakashi could've done to convince him not to chase darkness.

 

[kaka96]

Sarutobi Hiruzen for failing to stop the Uchiha massacre and Orochimaru from going rogue, leading to the death of many, betrayals to the village.
Which later led to much more, but he didn't get to regret it since he died >.>

This or J-man for failing to stop Oro, protect Minato or Sarutobi and many other things >.>

 

[Stark]

Madara not raping Obito when he had the chance, now Obito can use ST to escape..


I keed xd, but biggest regret is Madara trusting Nagato

 

[Retsu]

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Pure unadulterated regret right here. Felt a lump in my throat from Nagato wanting to be able to help the good guyz instead of being an OP pawn.

 

[Kenpai]

Kishi's abandonment of the hyuuga clan. So much potential for a epic story. Focus on the Rinnegan and Sharingan...why not bring the byakugan into the equation and make it epic.

 

[ziggyZ]

I actually think it should be on obito's part, since of he had not given Kakashi his left eye. No one would be able to stop him.

 

[kyubbi sagemode]

Oro not killing nagato

 

[wargear]

Jiraiya dying without Tsunade smothering him with her bazookas.... xd

 

[Makoto]

Biggest regret? I'd have to say Itachi not trusting Sasuke with the truth.

 

[ForbiddenUzumaki]

Sakura acting like a bitch with naruto the whole time until realizing how strong he became and all the things he accomplished compared to her.
The way she was acting with Naruto was really annoying, hope she regrets it good now.