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Volgin doing what he does best.

"Colonel Vermon CaTaffy! The single most feared terrorist on the planet, a psychopath bent on dominating the world, his nature so cruel as to verge on insanity. He was a total paranoid, his deeds those of a madman.
Colonel CaTaffy was dictator for life of his small but incredibly wealthy and savage desert country, Nouria. CaTaffy's sole purpose in life was to bring the democratic nations to their knees. His terrorist actions were hideous, violent, always unexpected.
And always effective, because they struck fear into the hearts of world leaders. CaTaffy bombed civilian aircraft, killed innocent people, took non-combatants hostage, and tortured them without mercy."

In a franchise where many antagonists have loved ones, standards, or well-intentioned goals, these select few stand out as utterly reprehensible figures.

Entries for each group are by approximate release/publication date.

All spoilers are unmarked. You Have Been Warned!

Canon Games

  • Metal Gear Solid 3: Snake Eater: Yevgeny Borisovitch Volgin is a Psycho Electro Soviet colonel whose history is replete with awful violence. Within minutes of appearing, Volgin fires a Davy Crockett nuke at his countrymen just to give it "a test drive", knowing full well that he won't be blamed for it. A cruel sadist who gets off on the pain of others, Volgin abuses his "lover" Tatyana—actually EVA in disguise; arbitrarily suspecting one of his own men might be a spy, tortures him by beating him within a drum can, eventually killing him; and subjects Naked Snake to a vicious round of torture that ends with Naked Snake less one eye, intending to visit further cruelties on him later. Volgin, with the Philosopher's Legacy, intends to overthrow Khrushchev, take over Russia, and throw the entire world into a storm of violent uprisings and war with his mass-produced weapon, the Shagohod.
  • Metal Gear Rising: Revengeance: Sundowner led Desperado Enforcement LLC and Desperado's Winds of Destruction. Selling weapons and technology to terrorists, Sundowner instigates war, which he believes to be the natural state of man. Sundowner comes up with a project to create his own army by kidnapping hundreds of homeless children from third world countries and having all of their organs removed, keeping the brains, which he puts in a realistic VR simulation of war to brainwash them into becoming killing machines; he sells the rest on the black market. Sundowner starts the plot by gleefully murdering African Prime Minister, N'mani, and all his guards, while using the Metal Gear RAY unit to spread destruction all over the city, solely to ensure that Africa descends into war once again. Sundowner later assists Senator Steven Armstrong in trying to create widespread conflict.

Non-Canon Games

  • Metal Gear (NES version) & Snake's Revenge: This non-canon version of Big Boss is lacking all redeeming qualities of his canon counterpart. Leader of Outer Heaven, Big Boss kidnapped Dr. Drago Pettrovich Madnar and forced him to create Metal Gear, a bipedal Walking Tank capable of launching nuclear missiles from anywhere in the world, threatening to kill his daughter, Ellen Madnar, if he refused. Solid Snake managed to destroy his Metal Gear, free his prisoners, and blow up his base, leading to Big Boss barely surviving, but needing to replace his damaged body parts with cybernetics. Desiring revenge, Big Boss started to recreate Metal Gear, planning to use it to launch nuclear strikes across the whole world, with the first targets being New York, Tokyo and Moscow.
  • Metal Gear Ac!d2: General Wiseman, a member of the Joint Chiefs of Staff, was the mastermind behind the horrific event known as the Praulia Massacre. Thinking that the data about the Model 2 soldiers was insufficient, he had the technicians provoke said soldiers into going berserk, causing the deaths of 10,000 people. After this, he sent the Model 3 soldiers in to eliminate the Model 2 soldiers, despite knowing that eliminating their brethren hurt them. These actions resulted in death of Dr. Thomas Koppelthorn's wife—which Wiseman pinned on Snake—resulting in Koppelthorn threatening to launch a nuclear attack unless those responsible for the death of his wife were handed over. Sending Snake and Venus to stop Koppelthorn, Wiseman in reality used them to destroy any evidence of his involvement in the Praulia Massacre, planning to dispose of them as well when they finished, resulting in Snake's amnesia.

Metal Gear Solid comic series by IDW Publishing

  • Liquid Snake is one of the three clones of Big Boss, who was jealous of his status as the most inferior. Growing to hate Big Boss, Liquid became furious upon hearing that Solid Snake killed him; angry that he "stole his chance for revenge", Liquid organized a scheme to take over the nuclear base on Shadow Moses, using his FOXHOUND unit to get his hands on a new Metal Gear Rex, which he planned to use to force the US government to hand over the body of Big Boss, and when they refused, he has DARPA Chief Donald Anderson and ArmsTech President Kenneth Baker tortured for the codes to launch Metal Gear. When that failed, he manipulated Solid Snake into activating Metal Gear and tries to kill him with it, brutally crushing to death Solid Snake's ally Grey Fox, who he had previously brainwasher, in the process. Managing to survive by possessing the body of Revolver Ocelot, Liquid first managed to take over his body when he was about to steal Metal Gear RAY from USS Discovery tanker, and used this Metal Gear to tear this tanker apart, killing dozens of people who were onboard the tanker. Taking over Ocelot's body again, when Ocelot betrayed Solidus Snake and taken over Arsenal Gear, Liquid sent Arsenal Gear towards Manhattan, escaping before it crashed into the city, destroying a big part of it.
  • Sons of Liberty:
    • Solidus Snake is the self-proclaimed best of the 3 clones of Big Boss and former President of the United States, who was deeply involved in the First Liberian Civil War, personally going into the field and killing countless people, innocent and otherwise. Building his army of Child Soldiers there, Solidus at one point killed the parents of Jack and adopted him, and makes another child soldier for his army from him by abusing him his entire life and forcing him to commit murders, like during his 10th birthday he forces Jack to brutally kill 10 of his hostages as a "birthday gift". After Jack was taken away from him by the Patriots, an angry Solidus created a plan to overthrow the Patriots. When the Patriots found out about this, Solidus escaped, bombing a Paris hotel as a cover up, framing Solid Snake in the process. Solidus attempted to extract the brains of a grown-up Jack, who became known as Raiden. Solidus wanted to kill the Patriots and be hailed as a hero by the public for returning their freedom.
    • Fatman, aka "The Emperor of Explosives", is one of the members of the Dead Cell terrorist group and the vilest of them all. Having a fascination with bombs, Fatman, as a child, creates a nuclear bomb, thus earning his nickname after the bomb dropped on Nagasaki, and while still a child he killed at least one of his classmates by blowing him up, all because he wanted to build himself a name and hated that classmate for daring to think himself smarter than Fatman. Helping Dead Cell commit their crimes by creating explosives and assisting them in taking over the Big Shell facility, Fatman became a spy for the Patriots, just for the chance of killing his former mentor Peter Stillman. Chaotically blowing up parts of the facility solely to kill Raiden, Fatman rigged the entire facility, desiring to destroy it and to kill all hostages and his own teammates, if either Raiden or Stillman would have bested him.

Other Media

  • Metal Gear (Worlds of Power): Colonel Vermon CaTaffy is the dictator of the small, but wealthy, country of Nouria. CaTaffy always hated "the free world" and wanted to bring it to its knees. Constantly committing atrocities, like the bombing of civilian aircraft and the torture of civilians and non-combatants for fun, CaTaffy decided to build his own Weapon of Mass Destruction, kidnapping Doctor Pettovich and his daughter Ellen, to force Pettovich to build him Metal Gear, threatening to kill his daughter,if he refused. When the US military sent nearly all Snake Men to Outer Heaven to stop CaTaffy, he managed to capture them and tortured them all, some fatally. After his Metal Gear was complete, CaTaffy tried to launch the nukes at Washington, London, Tokyo, Canberra and Paris to "destroy the free world".
  • Metal Gear Solid (1998-1999 Japanese audio drama): Sergei Ivanovich is a partner of the commander of the Esteria Army Special Forces, Mark Cortez, in an attempt to overthrow the local government in South America. In reality using Cortez for a scheme of his own, Ivanovich has Cortez assist him in capturing Colonel Ray Campbell in the planned ambush, killing Cortez's entire unit in the process. From there, torturing Campbell for fun, he uses his life signal to lure Solid Snake and Meryl to him, promising to torture them all to death. Ivanovich reveals his plan to extract the FOXDIE virus from Solid Snake, so that he could use it to create a biological weapon to use against the government and innocent people; Ivanovich turned on Cortez, mortally wounding him, before killing the arriving soldiers, and then trying to sadistically kill Campbell, Meryl and Solid Snake.