After Frank Castle lost his family in a mob hit gone wrong, he reinvented himself as The Punisher; a one-man army with the sole purpose to end all crime. No criminal is off limits to Castle. It doesn't matter if they have superpowers or diplomatic immunity. If someone is in his crosshairs, the Punisher will not rest until he puts them in the ground.
During his crusade, he has tangled with thousands of the sickest criminals that have walked the Earth. Drug-pushers. Serial killers. Sadomasochists. Cannibals. Most of them are small-time scumbags who are just trying to take down the Punisher to make a name for themselves.
But there are some villains that stand out. They are not just crazy. They are in their own league of evil. We're not just talking about a gangster or a supervillain. Castle has faced a sociopaths who amputates women for fun. He fought a dictator who unleashed an entire nation to kill Castle. He battled a warlock who used Castle's own dead family against him.
Here are ten of the most demented sickos the Punisher has ever faced.
10. The Holy
Although the Punisher believes he is wiping out crime, his actions have inspired many people to turn to vigilantism, often with disastrous consequences.
During confession, a priest called Hector Redondo heard a mass murderer asking for absolution for his sins. Enraged that the criminal thought he could avoid repercussions for his evil deeds, the priest snapped and hacked him to bits with an axe. The last thing the crook said was, "Holy!" before he was killed. Redondo saw this as a sign he was chosen to punish sinners and took on the name, The Holy.
He killed any person who entered his confession booth that he believed to be beyond redemption. He knew his actions were evil in the eyes of God but he didn't know how to stop killing. When The Holy read an article about the Punisher's goal to wipe out all crime, it compelled him to continue smiting the wicked. He found two vigilantes called Mister Payback and Elite who also took it upon themselves to slay criminals.
The trio tracked down the Punisher to thank him for inspiring their work and asked him to lead their group. Unsurprisingly, the Punisher shot them all dead.