Daredevil might be Marvel's best and most storied character, but seriously, the guy has not had it easy over the years.
Ignoring the character's tragic origin to begin with (which involved a young Matt Murdock being blinded by radioactive waste shortly before his father was murdered by the mob), the Man Without Fear has almost every other superhero beat when it comes to bad days - the mother of which arrived in a little 1986 comic by Frank Miller, called Born Again.
The comic, which Miller co-authored along with artist Dave Mazzucchelli, is often considered Marvel's best. It encapsulates the very essence of Daredevil's modern self, but while it's true that Born Again is a seminal comic book, there's no getting away from the fact that Matt Murdock has a rotten time of things throughout it, with the Kingpin of Crime (Wilson Fisk) orchestrating his downfall in a thorough, almost systematic manner, right from the safety of his New York apartment.
In many ways, Miller's tenure on Daredevil was typified by tragedy. The writer famously introduced the ambiguous assassin Elektra early on in his run, only to have her killed by Bullseye - formerly a gag character - in the months following. Born Again then went on to exacerbate things entirely by having Matt's former colleague and love interest, Karen Page, fall into a pit of addiction and be abused by an exploitative group of pornographers. Then, in a moment of pure desperation, Page sells Daredevil's secret identity for a shot of heroin. This information promptly finds its way to Kingpin who, having grown tired of Daredevil's constant harassment of his criminal empire, proceeds to make Matt Murdock's life a living hell - as he so often does.
Born Again wouldn't be the last time Matt Murdock had a bad day (crikey, you only have to look towards Brian Bendis' and Ed Brubaker's runs for confirmation of that), but it was the one that will forever live in infamy...