"Cristu told me something, about when you and him were starting out. Something you said. 'Rape them to break them.' Cristu didn't get it, but you explained. They had to be shown right away just who was in control. They couldn't stop you when you had them lifted off the streets. They couldn't stop you now. They had to understand that they were POWERLESS to prevent anything from being done to them."
- Avengers Confidential: Black Widow & Punisher can be found here.
- The 1989 film can be found here.
- The Netflix series can be found here.
- The 2005 video game can be found here.
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- Billy "The Beaut" Russo was a sociopathic hitman who helped arrange the deaths of the Castles and thought nothing of bombing a city block to get at a target. After his face was mutilated, Russo took the name Jigsaw, murdering innocents to frame the Punisher many times, leaving a massive trail of corpses behind him. Assisting Samuel Smith in trying to wipe out most of humanity, Jigsaw thinks nothing of murdering women and children, even abandoning his own son to die when it becomes a choice between his life and a few extra seconds to murder Frank Castle.
- Reverend Samuel "Sammy" Smith, aka "The Rev", was a Jim Jones-style figure who started his own cult called the "Church of the Saved". Preaching that America is a racist and fascist nation, Smith managed to recruit several disfranchised people to join his church. However, Smith runs his church as a fiefdom, killing members who defy him or try to leave the church and making the women of his church join his harem, while forcing everyone else in the church to be celibate. Punisher tries to kill Smith after he reveals he intends to feed poisoned food to his church membership, killing all 1,000 of his loyal followers. After his initial defeat, Smith decides evil is more powerful than good and begins to worship the demon Belasco, believing him to be Satan. Smith decides to use a drug that causes sterility to destroy the human race. After the Punisher destroys a shipment of his sterility drug, Smith take out his frustration by murdering a suburban family, including the children. Near the end of the story, Smith was trying to dump his sterility drug into the Gulf of Venezuela.
- November 1990's "St. Paradine's": Colonel Herbert Fedenia carves a uniquely depraved niche for himself even in spite of his status as a minor, one-shot villain. A seemingly-upstanding man who runs St. Paradine's, a military academy for children, Fedenia's true nature is revealed when Frank discovers Fedenia is a child pornographer who uses his unwilling cadets as his subjects, drugging them and having them brutalized on top of routinely having them raped. When one of the young cadets refuses to shoot Frank when he's ordered to, Fedenia simply attempts to murder the child himself.
- Punisher Summer Special's 1991 & 1992 issues: Colonel De Sade is a former military official who served with Frank in Vietnam. After bumping into De Sade at a military hardware expo, Punisher follows him and finds him robbing a bank. De Sade is about to use a knife on one of the customers, when the arriving police force him to flee. Punisher tries to stop De Sade but is captured in the process. De Sade tortures Punisher, but Punisher defeats De Sade and his men. Months later, De Sade escapes from prison, murdering a guard in the process. De Sade starts a new vile business venture producing snuff films. De Sade sends Punisher a video of his work, showing De Sade brutally murdering a young woman with a knife. De Sade's assistant Allison sets up fake auditions to lure in victims with promises of a dance show touring South America. After Punisher kills De Sade's men and saves the women at this fake audition, Allison flees to De Sade's studio, where De Sade forces Allison to be in one of his films when he runs low on extras. Punisher confronts De Sade, who tries to distract him by putting some of the women he captured into death traps, even threatening to kill Allison if Punisher does not back off.
- Punisher/Black Widow: Spinning Doomsday's Web, by D. G. Chichester et al.: Peter "Doc" Malum was a US government scientist who invented a weapon system, the Pluto Project, where jets with supersonic engines can deliver H-bombs to any target on the planet at the speed of sound. Malum, however, was secretly a Serial Killer who murdered people in his spare time. When the government finds out, Project Pluto is mothballed and Malum goes on the lam. Years later, Malum is captured by the FBI, but his gang breaks him free, with Malum brutally murdering several FBI agents. When Black Widow tries to stop Malum, Malum beats her up and spits on her to humiliate her. Malum plans to create his own version of Project Pluto, murdering government officials while stealing the parts he needs. When Malum's assistant Cassady states that he thought they are just going to use Project Pluto to blackmail the world, Malum murders him, intending to use Project Pluto to devastate the world, just for kicks.
- War Zone's "Dark Judgment" arc: Judge DuPrey, is a respected federal judge who is secretly the "Full Moon Killer", who has a double-digit body count. A smug Control Freak who gets off on having power over others, DuPrey butchers women and girls—in one instance killing a victim's dog alongside her—with a Sword Cane on nights with a full moon. A blackmailed mobster named Brazo, who is disgusted by DuPrey, reluctantly provides him with lookouts, and when Brazo is killed and replaced by a rival, DuPrey murders the man because he is not as sycophantic as Brazo was. Going on the run after this, DuPrey guns down two innocent bystanders while fleeing from an FBI agent and the Punisher. While fighting the latter, DuPrey waxes on about how much he enjoyed killing males for a change, and sneers that the Punisher sickens him and deserves to die because of how "mundane" and "unimaginative" his methods are.
- Purgatory: Lord Olivier is a Hell-Lord banished for his ambition and treachery even among his devilish compatriots. Growing up into a two-bit hood known as Frank Costa and regaining his memory of his demonic life upon his first murder, Olivier reinvents himself as a feared crime boss with a legacy of murder behind him. Desiring to get back at his fellow Hell-Lords, Olivier initiates Frank Castle's fall into the Punisher by having his family murdered, foreseeing that Frank reinvents himself as a brutal, murderous Anti-Hero so Olivier may enslave the souls of every criminal he kills for his army. Along the way, Olivier has angels hunted down by the hundreds and tortuously kills many himself, bathing in their blood to rejuvenate himself; tortures his loyal minions for failure; and ravages and conquers the realms of the other Hell-Lords one after another, not intent on stopping until Heaven and Hell are put under his tyrannical reign.
- "Army of One" arc: General Kreigkopf ("Warhead") was a former officer in the US Army who was kicked out due to his sadistic behavior. Kreigkopf fled to Grand Nixon Island, an island in the South Pacific, and turned it into a hub for criminals and mercenaries. Kreigkopf resurrects the Punisher's old enemy, the Russian, and sends him after the Punisher. After the Punisher defeats the Russian again, he goes to Grand Nixon Island to deal with Kreigkopf. When Punisher foils some of Kreigkopf's operations, he becomes enraged. There is a French military official on the island, using the island as a fueling depot before going to test a nuclear bomb in the Pacific Ocean. Kreigkopf steals the bomb and plans to drop it on Brussels, Belgium, feeling that no one would mess with Grand Nixon Island after that and he will get several new clients for his services after such a demonstration of power.
- "Black and White" arc: Guillermo Del Sol is a leader in the Dos Soles drug cartel, running most of the drug trade in Los Angeles. Guillermo is hired by elements of the U.S. government, who want to enact martial law, to commit a terrorist attack in Los Angles. U.S. government officials provide Guillermo with chemical weapons, which he tests on a small Mexican village, killing everyone there. Guillermo begins to mass produce the chemical weapons, planning to create enough to kill everyone in L.A. Guillermo also hired Electro to black out L.A., so emergency services will be busy when he releases the chemical weapons. Guillermo and Electro manage to capture Punisher, with Guillermo having Electro torture Punisher and eventually planning to sell Punisher to the highest bidder. When Punisher escapes, Guillermo flees, shooting one of his men for failing to stop the Punisher and blows up his HQ to cover his tracks, killing all of his men in that building.
- Becky Cloonan's 2016-2017 run: Face is a psychopathic mercenary working for Condor Private Military Company. Face is in charge of Condor's operation to distribute EMC, an experimental drug that gives people superhuman reflexes but also burns them out over time. Face has set up an office at a local insane asylum, where he is testing EMC on the inmates. Face also likes to remove the faces of his victims and place them on his office wall. Face is tasked with killing Punisher after Punisher attacks Condor's operations. Face kidnaps a DEA agent named Henderson and removes his face. When Punisher and another DEA agent named Ortiz confront Face at the asylum, he reveals he pumped Henderson and the asylum inmates full of EMC and sics them on Punisher and Ortiz. While escaping from the asylum, Face flags down a bus, murders all the passengers inside and hijacks it. After murdering some patients in an ambulance, Face kidnaps Ortiz and plans to cook and eat her, but seemingly overdoses on EMC. Face goes into a coma and awakens some months later, wanting revenge on the Punisher. Face goes to a local movie theater and takes hostages, threatening to murder a hostage every minute until Punisher faces him. Face has murdered half the theater's audience when Punisher confronts him.
- Darryl "Fearmaster" King juggles being a Corrupt Corporate Executive, The Don, a Serial Killer, and a Sinister Minister. When not ordering the demolition of inhabited neighborhoods and overseeing experimentation on the downtrodden as a part of his day job as a member of Alchemax Corporation, Fearmaster acts as the head of the Cyber-Nostra, and used his transformative powers on innocent women, disfiguring some and turning others into decorative statues for his amusement. And while he also used his abilities to revitalize those who attended his church, he had the rejuvenations be only temporary so that his congregation would become addicted to them and give him anything in exchange for them, including sex. Fearmaster's contempt for everyone around him also extended to his own allies; when the criminals that the Punisher had locked in his basement begged Fearmaster to let them out, the latter ignored them, and referred to the prospect of them all starving to death as a "bonus".
- Garth Ennis's run:
- Nicolas "Nicky" Cavella may seem polite, but in fact is so psychotic that even other Mafiosi despise him. Nicky started his career in murder when he was just a little boy by executing his parents and 12-year-old sister, conspiring with his aunt to gain control of the family. Later on, Nicky dealt with a particularly obstinate Chinese gangster by murdering the man's elder sons after having fed the man his youngest son, who was only in junior high school. Upon his return to New York following Frank Castle's rampage amongst the Cesare family, Nicky slaughters multiple people, betraying his own allies and throwing them to Frank to cover his own escape while also having his right-hand psychopath Pittsy torture and castrate a CIA agent for information. When he returns later, Nicky enrages Frank further by digging up the remains of his family and filming himself pissing on them. When his schemes meet a predictable end, Nicky attempts to escape by using a little boy as a hostage with a gun to his head. A Dirty Coward hiding under a tough guy exterior, Cavella was nevertheless the worst of the gangsters Frank had to face.
- William Rawlins was a sociopathic, greedy CIA operative who made his living as a leech in war zones. Betraying any ally for a quick buck, Rawlins once even threw his wife overboard to the Taliban rather than give up a shipment of heroin, resulting in her being repeatedly raped, something he later taunts her about. Going deep undercover in Saudi Arabia at the behest of a group of corrupt generals, Rawlins created a terrorist cell and used them to hijack a civilian airliner for a suicide attack on Moscow to create the illusion of a terrorist attack. When he later heads to Afghanistan on business, he has no compunction committing more betrayals and trying to see his vengeful ex-wife dead with Frank Castle. Betraying his benefactor, Rawlins slits the man's loyal second in command's throat and promises to find the man's young son and rape him to death in Moscow. Described as a parasite who lives only to make the world a hellish place he could profit from, Rawlins thought nothing of murder, betrayal or any other crime as long as he could earn more from it.
- "The Slavers" arc: Romanians Tiberiu Bulat, his son Cristu Bulat, and their associate (and Cristu's lover) Vera Konstantin are the titular slavers. Tiberiu and Cristu led an Eastern European militia during The Yugoslav Wars responsible for ethnic cleansing, slaughtering several entire villages until Cristu got the idea to take young women captive. They forced them into sexual slavery and went to the United States to export the business. Tiberiu is a sadistic, trigger-happy madman who'll kill anyone at the slightest provocation, while Cristu and Vera are practical business types, but just as evil, with Vera coming up with the strategy of "rape them to break them". These three are not above killing babies, as they send an email that shows the dead baby of an escaped victim.
- Barracuda, one of Frank Castle's most resilient and persistent enemies, is always ready with a laugh or a joke to conceal the black-hearted, soulless monster he truly is. Showing his sadism by trying to feed Castle and a gangster indebted to him to a great white shark, 'Cuda later betrayed a man who had worked with him for years simply because he got a better offer. After being defeated by Frank once, Barracuda, hungry for revenge, hunted down an ally of Frank's and murdered him and the man's wife for information before kidnapping Frank's infant daughter to torture her to death in front of Frank, with him booby trapping the baby's seat with a mine to kill both her and Frank. In Fury: My War Gone By, Barracuda is revealed to have once been a Green Beret in Nicaragua with a penchant for executing members of the government by chainsaw after trying to psychologically torture them. Perhaps his worst act is the revelation that he assisted in the atrocities of the Contras, entailing the wholesale rape, torture, and slaughter of several defenseless villages, adults and children alike butchered; to show how little the US uniform meant to him, 'Cuda kicked a decapitated child at Nick Fury. 'Cuda is also shown to be a rapist, and even strongly implied to indulge in cannibalism. Defined by selfishness, cruelty and his willingness to betray anyone for a buck, not even the "Barracuda charm" can disguise what a savage Barracuda truly is.
- "Girls in White Dresses" arc, by Gregg Hurwitz, Laurence Campbell, et al.: "The Heavy"—Jigsaw—is the racist, misogynistic co-leader of a large drug cartel. He and his associates have been terrorizing a Mexican border town by kidnapping women and girls—as young as twelve—and having them work literally to death as slave labor under terrible conditions in his drug lab. Frank notes that the number of crosses in a cemetery indicates the massive scale of the cartel. The Heavy tries to drive Frank away by placing an already-dead little kid at the scene of the shootout to make Frank believe he shot her. Aside from being a very Bad Boss, The Heavy plans to sexually assault one of the workers, and, when Punisher's closing in, orders his men to kill the remaining workers before they can talk to the police.
- "Naked Kill" one-shot, by Jonathan Maberry, Laurence Campbell, et al.: Mickey Fane, along with his lover Polly Hu and Mickey's nephew Eleventhree, run a horrific human trafficking operation. Taking monthly shipments of women and making rough pornography with them, they eventually force the women to kill one another until one can go free, only to make her film a video with Eleventhree, named for his massive size, to the point where Eleventhree simply rapes his victim to death. Polly also regularly brings Mickey girls to rape while filming Eleventhree in his movies. When Frank arrives, Mickey callously abandons Polly and Eleventhree to be killed in the security protocol as well, with Frank managing to save the girls, before ambushing Mickey himself when Mickey plans on a new shipment of girls to torture and kill.