- "They call me Il Pazzo. In English, that means I'm a crazy summanabitch! Don't you forget it!" -Il Pazzo
Il Pazzo is the leader of the Italian criminal organization Danger Danger. He also holds a grudge against Dmitrij Volkov calling him a Russian bastard. His real name is unknown and is only addressed by his nickname. Il Pazzo is determined to compete with H.A.R.M. and rise to the top of the criminal underworld. He has an unnamed brother and a nephew named Furio.
Throughout the first six chapters of Contract J.A.C.K., Il Pazzo is unseen and is only heard over the two-way radio John Jack is carrying. He speaks in a thick, stereotypical Italian accent laced with profanity.
Il Pazzo leads the assault on the Czechoslovakian Army secret launch facility to hijack a rocket so they can find Dr. Harij. The mad scientist was on the H.A.R.M. Space Station when it was hit by meteorites and survived the crash on the Moon. Il Pazzo believes that Dr. Harij's knowledge will help Danger Danger grow in the criminal community. When Jack (who was sent by Volkov to find out what Danger Danger was up to) becomes a pain in Il Pazzo's side, Il Pazzo becomes more obsessed with getting rid of Jack.
In the last chapter there is a brief glimpse of Il Pazzo as he sails away in his gondola with Dr. Harij. After Jack's successful rescue Dr. Harij, Il Pazzo is heard threatening John that he is dead.
- Il Pazzo in Italian means "The Madman".
- He appears to have dead-white skin, like the Joker.
- He is voiced by John Armstrong.