The man without fear, Daredevil, has fought many villains since his debut. Some were instantly a hit, like Bullseye or Elektra. Some grew into legend due to development by various writers, like the Purple Man and Kingpin. It ultimately boils down to how they were written by very talented creators.
And then there are some who never had a chance. That doesn't mean that there's no hope for them; it's just that there's not been anything too successful done with them to date. Someone could do something impressive with one of these villains, but some may prove more difficult than others. Without further delay, here are Daredevil's ten most pathetic villains so far.
10 Gladiator
The Gladiator began his life as a criminal because he was jealous of the super-heroes popping up in New York. He designed his costume and weapons, saw blades worn on his wrists. He then began a past time of being beaten by Daredevil.
He convinced himself that his choice of allies was his downfall. Despite an attempt to reform, he eventually went insane. Part of this was caused by exposure to psychotropic chemicals but regardless, the Gladiator completely lost his mind.
9 Jester
The Jester was a failed actor who turned to crime. Hailing from the Silver Age of comics, he took on the identity of a Jester, wielding gadgets that matched his practical joker theme. His fake broadcasts and commercials targeted Daredevil and one-time New York District Attorney Foggy Nelson. All his criminal activity ceased when he got to adequately play the role of Cyrano de Bergerac.
However, he returned to partner up with Screwball for a prank web-series. Unfortunately, they were stopped by a vicious beating from the Superior Spider-Man. He was sent back to prison on dubious charges where he was killed. Somehow, he returned to life and crime to be defeated again. Not that anyone cared, though.
8 Man-Bull
A lot of Daredevil's less successful villains have tragic backstories which, in the hands of better writers, could've made them compelling. On that note, Man-Bull was made to undergo an experimental transformation when Daredevil stopped him from kidnapping homeless people for the process. When the transformation became permanent, he started down a path of constantly being stopped by Daredevil.
He began to further mutate into a more animal form. He was sent back into prison numerous times, despite many escape attempts during massive breakouts and riots. He was even used for a great hunt by Kraven the Hunter and Arcade. Man-Bull managed to survive but returned to custody, this time to a rebuilt Ravencroft Institute, which he isn't busting out of any time soon.
7 Masked Marauder
The Masked Marauder saw himself as a criminal mastermind. His schemes were focused almost exclusively on Daredevil, which was convenient since he originally was Matt Murdock's landlord (yes, really). He tried to impress the organized crime families but failed miserably.
He became obsessed with learning Daredevil's identity but failed again. He failed so badly that he was believed to have perished and being legally dead, lost all of his legally owned properties. This drove him further into working for organized crime. He was last seen getting blown up in a villain-exclusive bar by the Punisher.
6 Matador
The Matador turned to crime after his career as a brutal bullfighter ended in disgrace and injury. He recruited and teamed with other villains like Man-Bull, Leap-Frog, Stilt-Man, and the Gladiator. Failure followed his efforts whenever he tried to resort to crime.
Like most of Daredevil's other pathetic villains, the Matador retired from villainy. He was still targeted by the vigilante group Scourge of the Underworld, but the assassin sent to kill him couldn't do it in front of the child Matador had been raising as a single father. He was later used by the Ringmaster but outside of that, he managed to stay retired. Good for him!
5 Turk Barrett
Turk isn't a super-villain but he has shown up enough times to become one of Daredevil's recurring foes. He's been depicted as an overly ambitious small-time crook, as seen in his numerous failed attempts to elevate his status in New York's criminal world. Often, he would steal other villain's equipment and always ran afoul of Daredevil.
Turk's closest brush with success came when he happened to come across the Mind Stone, which he used to create his own criminal empire. With this newfound power, he crashed a meeting of wielders of the Infinity Stones that was later attacked by Gamora. In the mess, Doctor Strange convinced Turk to give up the Mind Stone and teleported the crook to safety.
4 Stilt-Man
Stilt-Man stole the design for his stilts, which were hydraulic rams, from his employer. He continued to see his attempts at stealing money and technology thwarted not only by Daredevil but by his own incompetence. Whenever he squared off against other superheroes, his failures were almost as assured.
After numerous failures, Stilt-Man finally gave up when Matt Murdock was exposed as Daredevil. He got a little redemption in working for the government during Civil War but was killed by the Punisher. During his wake, his marriage to the villain Princess Python was revealed. Like the Jester, he was later resurrected to a resounding lack of fanfare.
3 Angar The Screamer
Angar the Screamer got his powers from Moondragon, who was trying to create allies against Thanos. Unfortunately, she was double-crossed by an associate who turned many of the creations to crime. Angar targeted Daredevil and Black Widow and managed to escape, despite being defeated. A later attack on Iron Fist left Angar badly injured by Colleen Wing.
Angar kept his hippie appearance longer than was necessary. Eventually, he formed a partnership with the similarly powered Screaming Mimi. After his death from a gunshot wound, Mimi eventually became the hero Songbird. Eventually, like many villains on this list, Angar was resurrected.
2 The Owl
The Owl had been covertly dabbling in criminal activities through money laundering for quite some time but when the IRS outed him, he resorted to the most logical solution imaginable: build his own criminal empire. He even started taking a formula that enabled him to glide in the air. When stopped by Daredevil, he fled to San Francisco but crossed paths with the crimefighter and Black Widow there as well.
The serum that the Owl had been taking had a debilitating effect on his legs. He kidnapped a specialist to remedy the problem. Unfortunately, the scientists boobytrapped the flying device and the Owl fell from the sky, barely escaping death. Subsequent efforts to establish a criminal empire ran him afoul of the Kingpin, the Hood, and the Shroud, all of whom were not as sparing as Daredevil.
1 Leap-Frog
Leap-Frog was a failed inventor who came across a successful invention in spring boots. Rather than finally get a patent, he decided to turn it to a life of crime because of course he did. He first encountered some success, dodging capture by Daredevil until he got too confident and failed to avoid an ambush. What followed was a string of failed attempts as both a super-villain and criminal.
His humorously bad luck is best summed up in his failed escape attempt in court, when he didn't notice that the fasteners on his boots had been removed and thus a shoe slipped off his feet while he was in midair. More failures (like teaming up with Stilt-Man, of all people) followed before he served his time and returned to his family. His son took one of the Leap-Frog suits and became the D-List hero Frog-Man, and Leap-Frog has since stayed retired. He didn't approve of his son's heroics, though.