Pain Is Pain; Its Not Something To Be Judged On The Basis Of 'Who's Pain Was The Worst'. Instead, The Level Of Suffering The Characters Have Had To Endure Due To The Pain Should Be The Premise Of The Question. That Being Said, Nagato, Naruto, And Sasuke All Suffered Pain. However, Naruto Was Able To Find Solace In The Bonds He Formed With Team 7 And Later On, Most Of Konoha. Nagato, In His Final Moments, Was Finally Able To Grasp Naruto's Words, And Thus, Was Freed From His Suffering. Sasuke, In Contrast, Is Still Suffering As A Result Of The Pain Intertwined With His Clan's Legacy And Itachi's Sacrifice, And As Such, Sasuke Has Endured The Most Pain Of The Three.