The John Wick franchise's criminal underworld is unlike any other. Spanning every corner of the globe, it exists as a secret society with its lore, governance, and own set of rules. It attracts the toughest of the tough — high-level assassins and ruthless criminals.
With millions of members, John Wick must cross paths with these villains, be they low-level thugs, other assassins, or criminal masterminds, as he fights his way through this world. While some of these antagonists scheme and strategize against John, others seem to be lacking in the intelligence department.
Iosef Tarasov
The son of Viggo Tarasov, Iosef kicks off the events of the series when he orders John Wick's dog killed, unaware that it belonged to the most feared assassins in the world. Enraged, John comes out of retirement to take revenge on those who crossed him.
Iosef has a distinct combination of hotheadedness and ignorance, something that catches up to him in the climax. When John finally has Iosef in his crosshairs, Iosef says "It's just a f*cking dog" before John shoots him.
Gianna D'Antonio
Gianna D'Antonio is the head of the Camorra crime family and a member of the High Table. John Wick is tasked by her brother Santino to assassinate her. After being held at knifepoint by a criminal angered by her actions, Gianna goes off to put on makeup alone, making it easy for John to ambush her while in her bathroom and complete the assassination.
Gianna's lack of awareness of the danger she is in, combined with how befuddling some of her decision-making is, shows that she is not the sharpest crime lord.
Santino D'Antonio
Gianna D'Antonio's brother Santino is forced to go on the run from a vengeful John when a hit on John goes wrong. It's never a smart idea to order a hit on John Wick, but Santino somewhat redeems himself by wisely holing up at the Continental hotel as it's the one place where he can't be killed.
Alas, Santino's thirst for power ultimately leads to his death. When they meet at the Continental, he unwittingly taunts John into breaking the hotel's no-killing rule.
Viggo Tarasov
Viggo Tarasov is a Russian crime lord forced to go on the defensive when Iosef kills John's dog. Knowing exactly what kind of trouble is coming, Viggo puts a bounty on John's head and forces Iosef to go into hiding.
Viggo is a calculated criminal who seems to be doing all of the right things to stop an unstoppable force coming his way. As he's about to finally escape on a helicopter, he lets his guard down and is ambushed by John, leading to his death.
Sofia Al-Azwar
An old friend of John's, Sofia is an assassin who ends up being John's key to the High Table when she takes him to her former boss in Casablanca. After a long gunfight, Sofia and John escape into the desert, where she ends up leaving him.
Aside from being just as skilled in combat as John, Sofia's smarts are also shown through her wise decision not to accompany John on his search for the Elder. At this point, John's mission is quite dangerous and Sofia would be putting herself in harm's way.
Cassian
Sent after John as revenge for Gianna D'Antonio's assassination, Cassian's big moment comes when he attacks John in the middle of a crowded train station. John is forced to come up with ways of fighting him without grabbing the attention of onlookers, ending in John silently stabbing him in the chest.
Motivated by money instead of revenge, Cassian is a cold and calculated killer that provides a formidable opponent for John Wick. He doesn't allow emotions to get the best of him, and instead is undone by John's pure skill.
Zero
Zero is possibly the toughest foe that John Wick has faced, and his students are ninjas sent after John by The Adjudicator. When John fights to defend Winston and the Continental, he must deal with Zero and his men.
Zero is a highly intelligent warrior who is able to predict almost every one of John's moves while in combat. In addition to having skilled proteges at his helm, Zero is a master martial artist, making this an extremely tough fight for John.
The Adjudicator
A no-nonsense agent of the High Table, The Adjudicator must deal with the desecration of the Continental Hotel by forcing Winston and other owners of neutral sites to step down so that the High Table can assassinate John Wick. They offer a peace treaty to Winston, which they use to get him to shoot John.
Like Winston, The Adjudicator is a master manipulator who isn't afraid to do whatever it takes to get what they want.
The Bowery King
The leader of a homeless shelter that doubles as an underground intelligence syndicate, the silk robe-wearing Bowery King assists John Wick with his objectives while maintaining the Bowery's status as a neutral site. Angered by his mistreatment by the High Table, the Bowery King invites John to join his fight against the High Table.
By establishing an interconnected web of ground-level spies, The Bowery King is privy to more information than most other members of the High Table, which he uses to his advantage. Fewer criminals in the underworld are smarter than him.
Winston
As the owner of the Continental Hotel, Winston holds considerable power in the criminal world. He helps define and enforce the rules of the criminal underworld while also using his power in order to preserve the status of the Continental after John desecrates it.
Winston's intelligence is shown mostly in his duplicity. By acting as a friend to both sides, he often manipulates those around him, including John and The Adjudicator, to get what he wants.