|“||You may think you've seen the last of me, but death cannot take me from you. I will be born again. Today you make me a legend.||”|
— Ryan's last words before his execution
Nothing is revealed about Ryan's early childhood history, including why he started killing in the first place. In 1998, he started killing, eventually claiming the lives of six women over a ten-month period. Eventually, in 1998 or 1999, he was caught during an attempted break-in and was somehow connected to the murders. Ryan was subsequently tried, found guilty, and sentenced to death. He spent nine years on death row. During that time, he got a number of female groupies and fans whom he would write poetic letters to since he, a narcissist, enjoyed the attention and had a flair for the dramatic. Among these fans were Chloe Kelcher, one of the jurors in his trial, and Shara Carlino.
Ryan also made origami figures, which later reached the market for serial killer memorabilia, along with other personal belongings and even his semen and blood. All of these items were distributed by one of his guards, Sid Rutledge, who smuggled them out of the prison. On the day of his execution on September 16, 2007, there were complications when the catheter dislodged twice. In the end, it took him nearly an hour to die. Ryan's last words were: "You may think you've seen the last of me, but death cannot take me from you. I will be born again. Today you make me a legend." Chloe later obtained his semen after his death and used it to impregnate herself. When she gave birth, however, the child suffered an illness and died.
The Angel Maker
Exactly one year following his execution, Chloe begins a spree of copycat murders, having begun to suffer from severe psychosis at that point. Prior to starting the killing spree, she dug up Ryan's grave and took his body. Eventually, she commits suicide by cop in the end after killing three and attempting to kill a fourth. During the majority of the investigation, local authorities believed that the killings were actually the work of Cortland himself, according to a tale that he still survived his botched execution. While the BAU searched Chloe's home, they find Ryan's body in a private compartment. It is assumed that the body was reburied following Chloe's death.
It was mentioned Ryan targeted women who excited him sexually, and that he was a narcissist whose only real love was for himself. Since he planned on killing nine women, each one corresponding to a constellation, he was presumably a mission-oriented killer. Given the severity of the injuries he inflicted on his victims before he raped them, he may also have been a necrophiliac.
Ryan would sneak into the houses of single women at night while they slept. He would enter their bedrooms, beat them to death with his fists, and rape them. It is not specified whether he raped them after they were killed or if they were alive and died slowly from their injuries, but, since Chloe Kelcher, Ryan's future copycat, replaced the beatings with bludgeoning with a hammer, the first is more likely. Next, he punctured the victims' stomachs post-mortem with a screwdriver in patterns of the Heavenly Waters constellations. He then crossed their arms, hence his nickname. He also opened all of the windows in the house, which was his way of letting the victims' souls out.
- January: Tina Banbury
- April: Julie Pargrove
- June: Natalie Evercroft
- August: Annette Gratton
- September: Unnamed victim
- October: Unnamed victim
- Note: Ryan intended to kill three other women to complete the constellations, but was apprehended and executed before he could carry out those murders.