History Monster / ThePunisher

* [[SinisterMinister Reverend Samuel "Sammy" Smith]], aka "The Rev", was a UsefulNotes/JimJones-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 [[TamperingWithFoodAndDrink 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 [[SterilityPlague 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, [[WouldHurtAChild including the children]]. Near the end of the story, Smith was trying to dump his sterility drug into the Gulf of Venezuela.

[[AC:''ComicBook/ThePunisherMAX'' (even DarkerAndEdgier than 616 Punisher)]]

** [[AxCrazy Nicolas "Nicky" Cavella]] may [[FauxAffablyEvil seem polite]], but in fact is so psychotic that even other Mafiosi despise him. Nicky started his career in murder when he was [[EnfantTerrible 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 [[FamilialCannibalismSurprise 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 DirtyCoward hiding under a tough guy exterior, Cavella was nevertheless the worst of the gangsters Frank had to face.
** [[SmugSnake William Rawlins]] was a sociopathic, greedy UsefulNotes/{{CIA}} operative who made his living as a leech in war zones. [[ChronicBackstabbingDisorder 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 [[SlashedThroat 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 [[{{Greed}} he could earn more from it]].

** [[PsychoForHire Barracuda]], one of Frank Castle's most resilient and persistent enemies, is always ready with a [[FauxAffablyEvil 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 [[ComicBook/ThePunisherPresentsBarracuda later]] betrayed a man who had worked with him for years simply because [[OnlyInItForTheMoney he got a better offer]]. After being defeated by Frank once, Barracuda, [[ItsPersonal 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 ''ComicBook/FuryMyWarGoneBy'', Barracuda is revealed to have once been a [[SociopathicSoldier 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 [[UsefulNotes/{{Nicaragua}} 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 [[ImAHumanitarian indulge in cannibalism]]. Defined by selfishness, cruelty and [[ChronicBackstabbingDisorder his willingness to betray anyone]] for a buck, not even the "Barracuda charm" can disguise what a savage Barracuda truly is.

''[[AC:ComicBook/ThePunisher2099]]''
* [[ArchEnemy Darryl "Fearmaster" King]] juggles being a CorruptCorporateExecutive, TheDon, a SerialKiller, and a SinisterMinister. 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".

* The [[Film/ThePunisher1989 1989 film]] can be found [[Monster/FilmOToS here]].

* ''ComicBook/ThePunisherPurgatory'': [[BigBad Lord Olivier]] is a [[DemonLordsAndArchdevils Hell-Lord]] banished for his [[AmbitionIsEvil 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 AntiHero 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, [[BloodBath 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.

* "Black and White" arc" Guillermo Del Sol is a leader in the [[TheCartel 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 [[DeadlyGas 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 [[YouHaveFailedMe failing to stop the Punisher]] and blows up his HQ to cover his tracks, [[BadBoss killing all of his men]] in that building.

* [[SinisterMinister Reverend Samuel "Sammy" Smith]] ("The Rev") was a UsefulNotes/JimJones-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 [[TamperingWithFoodAndDrink 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 [[SterilityPlague 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, [[WouldHurtAChild including the children]]. Near the end of the story, Smith was trying to dump his sterility drug into the Gulf of Venezuela.
* [[VillainOfTheWeek Colonel Herbert Fedenia]], from the November 1990 issue ("St. Paradine's"), carves a uniquely depraved niche for himself even in spite of his status as a minor, one-shot villain. A [[VillainWithGoodPublicity 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 [[WouldHurtAChild 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.
* [[NamesToRunAwayFromReallyFast Colonel De Sade]], appearing in the 1991 and 1992 issues of the Punisher Summer Special, is a former military official who served with Frank in [[UsefulNotes/TheVietnamWar 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 [[SnuffFilm 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 [[BadBoss 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 trap}}s, even threatening to kill Allison if Punisher does not back off.

* Judge [=DuPrey=], from ''War Zone'''s "Dark Judgment" arc, is a respected federal judge who is secretly the "[[SerialKiller Full Moon Killer]]", who has a double-digit body count. A smug ControlFreak who gets off on having power over others, [=DuPrey=] butchers women and [[WouldHurtAChild girls]]--in one instance killing a victim's dog alongside her--with a SwordCane on nights with a full moon. A blackmailed mobster named Brazo, who is [[EvenEvilHasStandards 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.

* [[InsaneAdmiral General Kreigkopf]] ("[[NamesToRunAwayFromReallyFast Warhead]]"), from the "Army of One" arc, 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 [[WretchedHive hub for criminals and mercenaries]]. Kreigkopf resurrects the Punisher's old enemy, [[HuskyRusskie 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 [[NukeEm 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.
* Guillermo Del Sol, from the "Black and White" arc, is a leader in the [[TheCartel 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 [[DeadlyGas 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 [[YouHaveFailedMe failing to stop the Punisher]] and blows up his HQ to cover his tracks, [[BadBoss killing all of his men]] in that building.
* [[AxCrazy Face]], from Becky Cloonan's 2016-2017 run, is a [[PsychoForHire psychopathic mercenary]] working for [[PrivateMilitaryContractors Condor Private Military Company]]. Face is in charge of Condor's operation to distribute [[FantasticDrug 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, [[PlayingWithSyringes where he is testing EMC on the inmates]]. Face also likes to [[TearOffYourFace 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 [[ImAHumanitarian 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.

** "The Slavers" arc: [[RuthlessForeignGangsters Romanians]] Tiberiu Bulat, his son Cristu Bulat, and their associate (and Cristu's lover) Vera Konstantin are the titular [[HumanTraffickers slavers]]. Tiberiu and Cristu led an Eastern European militia during UsefulNotes/TheYugoslavWars 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 [[AxCrazy sadistic, trigger-happy madman]] who'll kill anyone at the slightest provocation, while Cristu and Vera are [[PragmaticVillainy 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.

* [[ArchEnemy Jigsaw]] was originally [[AxCrazy William "Billy" "The Beaut" Russo]], a [[PsychoForHire 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 [[FrameUp 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 [[AbusiveParents abandoning his own son to die]] when it becomes a choice between his life and a few extra seconds to murder Frank Castle

* The [[Film/ThePunisher1989 1989 film]] can be found [[Monster/FilmMToR here]].

* ''ComicBook/ThePunisher'': [[AxCrazy Face]], from Becky Cloonan's 2016-2017 run, is a [[PsychoForHire psychopathic mercenary]] working for [[PrivateMilitaryContractors Condor Private Military Company]]. Face is in charge of Condor's operation to distribute [[FantasticDrug 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, [[PlayingWithSyringes where he is testing EMC on the inmates]]. Face also likes to [[TearOffYourFace 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 [[ImAHumanitarian 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.

[[AC:ComicBook/ThePunisherMAX (even DarkerAndEdgier than 616 Punisher)]]

* "Girls in White Dresses" arc, by Gregg Hurwitz, Laurence Campbell, et al.: "The Heavy"--[[spoiler:Jigsaw]]--is the [[PoliticallyIncorrectVillain racist, misogynistic]] co-leader of a [[TheCartel large drug cartel]]. He and his associates have been terrorizing a Mexican border town by kidnapping [[WouldHitAGirl women]] and girls--as young as [[WouldHurtAChild 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 BadBoss, 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.

* The [[VideoGame/ThePunisher 2005 video game]] can be found [[Monster/VideoGamesGToP here]].

[[AC:[[ComicBook/ThePunisher Earth-616]] Punisher]]

With ''ComicBook/ThePunisher'' being DarkerAndEdgier, and the BlackAndGrayMorality of Frank Castle being an AntiHero who's [[PayEvilUntoEvil willing to kill]], to be a CompleteMonster, one must REALLY stand out.

[[AC:[[Franchise/MarvelUniverse Earth-616]] Punisher]]

[[AC:[[Franchise/MarvelUniverse 616]] Punisher]]

* The [[Film/ThePunisher1989 1989 film]] can be found [[Monster/FilmJToQ here]].

* The [[Film/ThePunisher1989 1989 film]] can be found [[Monster/FilmKToR here]].

** [[AxCrazy Nicolas "Nicky" Cavella]] may [[FauxAffablyEvil seem polite]], but in fact is so psychotic that [[EvenEvilHasStandards even other Mafiosi despise him]]. Nicky started his career in murder when he was [[EnfantTerrible 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 DirtyCoward hiding under a tough guy exterior, Cavella was nevertheless the worst of the gangsters Frank had to face.

** "The Slavers" arc: [[RuthlessForeignGangsters Romanians]] Tiberiu Bulat, his son Cristu Bulat, and their associate (and Cristu's lover) Vera Konstantin are the titular [[SlaveryIsASpecialKindOfEvil slavers]]. Tiberiu and Cristu led an Eastern European militia during UsefulNotes/TheYugoslavWars 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 [[AxCrazy sadistic, trigger-happy madman]] who'll kill anyone at the slightest provocation, while Cristu and Vera are [[PragmaticVillainy 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.

** [[SmugSnake William Rawlins]] was a sociopathic, greedy {{CIA}} operative who made his living as a leech in war zones. [[ChronicBackstabbingDisorder 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 [[SlashedThroat 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 [[{{Greed}} he could earn more from it]].

* [[SinisterMinister Reverend Samuel "Sammy" Smith]] ("The Rev") was a UsefulNotes/JimJones-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 [[TamperingWithFoodAndDrink 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 becomes a Satan-worshipper. Smith decides to use a [[SterilityPlague 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, [[WouldHurtAChild including the children]]. Near the end of the story, Smith was trying to dump his sterility drug into the Gulf of Venezuela.

* [[NamesToRunAwayFromReallyFast Colonel De Sade]], appearing in the 1991 and 1992 issues of the Punisher Summer Special, is a former military official who served with Frank in [[UsefulNotes/TheVietnamWar 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 [[SnuffFilm 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 [[BadBoss 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 trap}}s, even threatening to kill Allison if Punisher does not back off.

* Guillermo Del Sol, from the "Black and White" arc, is a leader in the [[TheCartel Dos Soles drug cartel]], running most of the drug trade in Los Angles. 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 [[DeadlyGas 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 [[YouHaveFailedMe failing to stop the Punisher]] and blows up his HQ to cover his tracks, [[BadBoss killing all of his men]] in that building.

* Guillermo Del Sol, from the "Black and White" arc, is a leader in the [[TheCartel Dos Soles drug Cartel]], running most of the drug trade in Los Angles. 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 [[DeadlyGas 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 [[YouHaveFailedMe failing to stop the Punisher]] and blows up his HQ to cover his tracks, [[BadBoss killing all of his men]] in that building.

''[[AC:ComicBook/ThePunisher2099]]''
* [[ArchEnemy Darryl "Fearmaster" King]] juggles being a CorruptCorporateExecutive, TheDon, a SerialKiller, and a SinisterMinister. 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".