Viggo would have been more than happy to see John stay retired forever, but his stupid progeny decided to fuck with the metaphorically sleeping boogeyman.
We’re going to take a minute to play devil’s advocate here and have some sympathy for Michael Nyqvist’s Viggo Tarasov.
He knew from the start that he would really have no chance against the titular assassin, raising the price on his head at every opportunity, but he does give it the old college try in the movie’s final fight sequence.
Sure, the guy is a monster in the sense that he makes money entirely based on the suffering of others, but he basically got dragged kicking and screaming into the plot of the first John Wick thanks to his idiot son.