Let's face it, Matt Murdock has it bad. He's perhaps only outdone by Tony Stark.
- Mister Fear driving Milla insane, and Matt trying so hard to find the cure for her that he actually ends up not being there for Milla... and it turns out there's no cure.
- Elektra's death. One of the monumental points of Frank Miller's career.
- When the Kingpin leaves New York after Vanessa's death, he finds a new love called Marta, and he bonds with her and her children. But he keeps thinking to himself that his happiness is fleeting, and that he'll lose them. But after months of living this way, he eventually stops thinking like this, mostly... then Lady Bullseye shows up with the Hand and kills them. Kingpin's response? "Yes... Yes, of course." The man has experienced so much tragedy that, even when enraged, it doesn't even surprise him anymore.
- Guardian Devil, the arc involving the death of Mysterio as written by Kevin Smith. Taking place JUST after Peter retired as Spider-Man, Mysterio is dying and just wants to show everyone he's not a joke, yet Matt keeps brushing off his attempts and lists off why his plans are just rehashes. Break him by driving him mad? Kingpin already did that. Mess with him spiritually? Armageddon already did that with the X-Men. And at the end of it Mysterio just says 'I guess I'll rip off Kraven now' and shoots himself in the head. One of the saddest lines from him were directed at Matt which were "If people think I'm a C-List villain. Might as well take down a C-List Spider-Man."
- The arc itself is also hellfire for Matt- Karen gets a false diagnosis of HIV, and then dies in the crossfire of a fight between Matt and Bullseye, Foggy nearly loses his mind thanks to Mysterio making him think he killed someone, and Matt himself ruins his friendship with Black Widow, though he reconciles with her at the end.
- Matt's love life is almost comically tragic- Karen and Elektra both die at the hands of Bullseye, Echo was killed by a brainwashed Elektra, Heather Glenn committed suicide after she felt Matt was ignoring her and she spiralled into a drug problem, Glorianna O'Brien is killed by one of Kingpin's assassins and Milla Donovan, who was driven insane by Mister Fear. Matt's only healthy relationships where both people lived after they broke up were with Typhoid Mary, a schizophrenic who frequently tried to kill him, and Black Widow, a former Red Room assassin.
