August 27, 1964 - Paul Bernardo

Bernardo's crimes unfolded across two distinct phases — a years-long series of sexual assaults in suburban Toronto, followed by murders carried out with his then-partner — giving investigators an unusually complex case that exposed significant failures in how early forensic evidence was handled. The involvement of Karla Homolka, and the plea arrangement that secured her relatively brief sentence in exchange for testimony, drew lasting controversy about how the justice system weighed culpability between the two. The murders of three young women, including Homolka's own sister, and the videotaped evidence that later emerged, made the case one of the most disturbing in Canadian criminal history.

From Wikipedia

Paul Kenneth Bernardo (born August 27, 1964), also known as Paul Jason Teale, is a Canadian serial rapist and serial killer dubbed the Scarborough Rapist and Schoolgirl Killer. He initially committed a series of rapes in Scarborough, Ontario, a district of Toronto, between 1986 and 1990, before meeting Karla Homolka, with whom he committed rape leading to the death of her sister Tammy, followed by two murders in 1991 and 1992.

After his capture and conviction, Bernardo was sentenced to life imprisonment and was declared a dangerous offender, making it unlikely that he will ever be released from prison. Following his conviction, Bernardo confessed to ten more rapes committed a year before the spree officially ascribed to the Scarborough Rapist. Homolka was given a lighter sentence in exchange for testifying against Bernardo as part of a controversial plea bargain; she was released from prison in 2005. Bernardo has been denied parole three times.

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