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Of all of them, Kirill is the only one that can actually defeat John in a fight, and came the closest to killing him.
He is portrayed by Daniel Bernhardt.
When John Wick invades the club Iosef visits, he is spotted by Kirill who watches the camera feed in a control room. Kirill recognizes Wick, draws his weapon and storms out of the room. After John manages to kill a whole divison of Kirills men, he gets shot by Kirill, but survives thanks to a bullet proof vest. Kirill manages to disarm Wick and a fight erupts. But John may have underestimated Kirill, as he defeats John within moments, beating the hell out of John, before throwing him off a balcony, but in return gets almost shot by John who still had a gun hidden in his belt. Kirill survives the shootout at the club, as did Losef, cause their brawl allowed Losef to escape unharmed.
Krillin later drives a car during John's ambush, knocking John out cold
Later, he is ordered to kill John Wick who by then was captured by Viggo Tarasov. He and another henchmen try to suffocate John with a pastic bag, but his assistant gets shot by Marcus, who observed the situation with a sniper rifle. John manages to break free and fights against Kirill, after a long violent fight, John strangles Kirill to death with his handcuffs still on.