When Chris becomes enraged about rumors that Adriana and Tony are having an affair, he pulls a gun on Tony, who is ready to kill him for doing so. He is spared only after Tony Blundetto. Scene from:Season 6 Episode 18 "Kennedy and Heidi"

Tony Kills Chris
Tony gave Chris so many chances and passes because of their relationship. He indulged his weaknesses because they were close. The car crash, and realizing Chris could have killed his.