* [[spoiler:Ghost-Peter struggling to remember his name as his identity is wiped out. Seeing him broken like that so that Otto can remain Spider-Man was heartbreaking.]]
** [[spoiler:Ghost-Peter forgetting who Uncle Ben was in the process was particularly heart breaking.]]
* The fallout from the "Run, Goblin, Run" arc. Norah Winters has lost her job because she was too close to Phil, Ben Urich has had his nephew arrested and must take time off work since the unmasking was too public for the Bugle, Phil has lost everything and has switched over to full time villainy under the Green Goblin. Given that at one point he tried to be a hero, it makes his fall even more tragic.
* The fallout from the Spider-Man 2099 arc is bitter over all:
** [[spoiler: [[TheBadGuyWins Ty Stone destroyed Horizon and they can't prove it because Otto knocked out Miguel O'Hara and deleted Peter's memories.]]]]
** [[spoiler: Max Modell losing his faith in Spider-Man and Peter because of Otto, his last act being to bring him back from the time implosion.]]
** [[spoiler: Aunt May heartbroken that Peter missed dinner with her, because he didn't just retreat when the bomb went off since Otto's ego was too great.]]
** [[spoiler: MJ calling it quits with Peter entirely.]]
* Otto forcing himself to turn down his old flame Stunner, who once sacrificed herself to bring him BackFromTheDead.
--> '''Stunner:''' [[http://abload.de/img/superiorspider-man0214vf8z.jpg It's a miracle! I never should've doubted you. I should've known you'd find a way back to me. Wait! Otto, this means we can be together. We can finally have everything we always--]]
* Carlie [[spoiler: mourning Peter over Otto Octavius's grave and apologizing for not figuring it out in time]].
* The Sandman's BreakingSpeech to [=SpOck=] and [[spoiler: subsequent death]] in ''Superior Spider-Man Team-Up'' issue seven are incredibly depressing.
-->'''SpOck''': Don't let this happen! You're not like the others!!!
-->'''Sandman''': [[BrokenPedestal That's what I thought about you.]]
-->'''Sandman''': Even when we fought before, even when you '''tortured''' me... Never did I think you would '''violate''' us like this!
-->'''SpOck''': You have to listen, you don't understand.
-->'''Sandman''': I don't care anymore! [[DramaticIrony Dr. Octopus was right, let this city burn!]]
-->'''Sandman''': I remember once... once I believed in you. That part of me is dead.
* Carlie [[spoiler:being turned into a Goblin as she screams for her sister to stop. The change afterwards is disturbing.]]
* Lamaze's [[spoiler:HeroicSacrifice in #29 and watching just how far Jameson has fallen as long as he can kill Spider-Man.]]
* Annual #2 and Ben Urich realizing that he's truly lost his nephew to the hold of the Goblin.
* Otto's [[spoiler:HeelRealization and HeroicSuicide, begging Peter to save Anna Maria and that ''he'' was the Superior Spider-Man]]
* In the end, [[spoiler: Peter himself laments that someone had to die so that he could live.]]
** To put this in context, [[spoiler:the man he's mourning was the same one who hijacked his body and spent the last couple months utterly destroying his (Peter's) life. And Peter ''still'' mourns him.]]
* Before he was [[spoiler:utterly broken by the events of "Goblin Nation"]], Otto was on the verge of proposing to Anna Maria. This makes his [[spoiler:HeroicSuicide]] all the more tragic.
* Otto's eventual fate. As arrogant and condescending and thoughtless as he was, all he wanted was to be a hero, to help people, to make the city a better place. He tries so, so hard to do the right thing, and in the end, he realized the dark side of "great responsibility"-[[spoiler: sometimes you have to die so others can live.]]