Ray Donovan and Sydney Manning

Raymond "Ray" Donovan (played by Jonathan Tucker) and Sydney "Syd" Manning (played by Adrienne Palicki) were a pair of young lovers who went on a killing spree together in The Thirteenth Step.

Background
Raymond Donovan was born in North Dakota around 1984 and was regularly molested by his alcoholic father. At the age of 10, he was placed in foster care due to drug problems, where he continued acting out by drinking, doing drugs and abusing people. In total, he spent time in four different foster homes. He was later arrested twice for driving under influence and his junkie girlfriend, Amy Wichowski, filed a restraining order against him. He later started going to help meetings to get rid of his addictions. At one of those meetings he met Sydney Manning. She was born on October 14, 1985 in Spokane, Washington, but her family later moved to North Dakota. Molested by her father frequently during her childhood, she was eventually placed in foster care in Billings, Montana. On April 12, 2007, she received a citation for driving under the influence and had to pay a fine, but didn't serve any jail time. On December 20, 2010, she caused a hit-and-run accident while under the influence of alcohol and heroine and was sentenced to mandatory rehabilitation after being paroled. At a meeting, she heard Ray open up about his substance abuse and how he was molested by his father and fell in love with him. Unfortunately, she also realized that he still had feelings for Amy Wichowski and got her out of the way by giving her alcohol and heroine, indirectly causing her to overdose and die. After that, she and Ray started going out and killing people across Montana and North Dakota.

Season Six
In the beginning of The Thirteenth Step, Ray and Sydney stop at a gas station in Miles City, Montana. Inside, they discuss getting married. Though Ray wants to, Sydney is not as certain. When the clerk begins making cracks about marriage, Ray pulls out a gun and starts firing at him while Sydney draws a revolver and shoots at customers. The attack leads to the BAU being called in. The pair then get a wedding license and get married. As the members of the BAU are being briefed, Ray and Sydney have already started another shooting at a gas station in Billings, Montana, dressed in impromptu wedding attire and sometimes kissing between the killings. After making out in their pickup, Sydney uses a cigarette to light a line of gasoline and blowing up the whole gas station, remarking "That...was awesome" to Ray's camera phone. The pair then drive away, laughing and declaring their love for each other. Upon investigating the crime scene, Derek and Hotch find grains of rice all over the floor and realize that the UnSubs are newlyweds.

Ray and Sydney get a room at a motel and consummate their marriage. They talk about their future and think about moving to Aruba and living by the ocean. Ray asks how she wants to spend their honeymoon. Sydney tells him "Exactly the way we've spent the last twelve months". Ray later attends a help meeting while Sydney waits in the car and drinks when a man stops by and starts flirting with her. She is quick to reciprocate and offers to have sex with him for $20. Ray tells the attendants about how his father drank and would molest him. When he is done and another attendant asks him whether he has done step seven of the recovery process, admitting his shortcomings, Ray becomes defensive and pulls out a gun and starts shooting. Sydney, having knocked down the man outside as they were engaged in foreplay, walks in carrying a pair of revolvers and joins in. As they leave, Ray shoots the man who tried to have sex with Sydney. While the BAU give the profile to investigators, Sydney suggests that they do step nine, make amends, and take it up with the source: Ray's father. After going to his old home, they force Ray's father and mother inside at gunpoint and Ray loads a revolver with a single bullet. He then holds it to his father's head and tries to make him confess to molesting him, pulling the trigger every time he denies it. Eventually, Sydney finishes a bottle and kills Mr. Donovan herself. The two then leave while Ray angrily yells at Sydney for killing his father before he could.

After driving away from the house, Ray pulls over by a road and starts fighting with Sydney, who tries to get him to hit her. As he holds her at a chokegrip against a tree, she starts unbuttoning his pants. They quickly make up and start kissing. They then drive to Spokane, Washington to Sydney's father's gas station and hold him at gunpoint, forcing him to also go through step nine and confess to molesting Sydney. When he denies it, she pistol whips him to the floor. When he apologizes and claims to have found God and changed, Ray brutally beats him while Sydney spurs him on. Mr. Mannings new daughter, Heather, then steps in and asks for her father. While Ray takes him to a private room and shoots him, Sydney promises the daughter to take her away, believing her father to have molested her as well. As they step outside with her, Prentiss and Derek are there, having tracked them down. A gunfight ensues, during which Derek hits Sydney in the shoulder, forcing her and Ray inside. When the rest of the BAU and SWAT arrive, Hotch calls Ray, who asks to talk to Derek. They demand a car, tickets to Aruba, gauze for Sydney's wound and alcohol. After Derek delivers the medical supplies and alcohol, he calls Ray and tells him more about Amy Wichowski's death. While Ray had previously thought she committed suicide, Derek tells him that heroine was found in her system; though she had never used that before that day, Sydney regularly used it in combination with alcohol, which is what killed Amy. As Ray begins to realize that Derek is telling the truth about Sydney indirectly killing Amy, Derek tells him about Sydney's likely responses to being questioned about it. As predicted, she first tries to avoid the question while thinking of a good answer. When Ray pushes her further, she tries a sexual distraction, suggesting they have sex on the spot. As they get down on the floor, Ray grabs her throat and strangles her to death for lying to him. Horrified by what he has done, he sends Heather out the door and backs out a window with an SUV with Sydney's body in the passenger seat, firing indistinctly at the police, before eventually being shot to death.

Modus Operandi
Ray and Sydney used firearms for most of their killings. Ray's handgun of choice was a semi-automatic Beretta 92F while Sydney used a revolver. Ray also used a pump-action shotgun. Their initial favorite target was gas stations. Though the first shooting was apparently a spur of the moment decision, their second was more planned, as they sealed the entrance with a padlock before they started shooting. At that attack, they used a crowbar and a baseball bat to kill some targets. They ﻿also sodomized the clerk, a middle-aged man, with a tire iron before beating him to death. Additionally, they apparently left one customer alive so that he could be finished off by the explosion Sydney caused.

Profile
The UnSubs are a couple, late teens to early 20s in age, from North Dakota who may recently have gotten married. Alcohol plays a role in their crimes and allows them to kill freely and uninhibited. Their victims are surrogates for people from their lives responsible for deep emotional and psychological wounds. The fact that they changed target from gas stations to an alcohol support meeting suggests that one of them may have a slight moral compass that led them to get help. The BAU believe one of them is a sociopath while the other is a psychopath. Though the definitions are similar in terms of pathology, a sociopath is less likely to engage in criminal activity and can be lured by someone dominant. A psychopath, on the other hand, is a consummate leader and likely to destroy anyone or anything in their way. Given that Sydney indirectly killed Amy to get her out of her way and the fact that Ray was the one who willingly attended a support meeting, it is likely that she was the psychopath while he was a sociopath.

Known Victims

 * December 20, 2010: An unspecified hit-and-run accident caused by Sydney
 * 2010: Amy Wichowski
 * January 2, 2011, Jamestown, North Dakota: N. Apu
 * January 4, 2011, Bowman, North Dakota: Unnamed convenience store clerk
 * 2011: Six killed in the Miles City gas station shooting, including the clerk
 * 2011: Eight killed in the Billings gas station shooting, including the clerk
 * 2011: At least eight killed in the Alcoholics Anonymous meeting shooting. Named victims are:
 * Jason
 * 2011: Paul Donovan
 * 2011: Mrs. Donovan
 * 2011: The attack at the Spokane gas station:
 * Gary Manning
 * Heather Manning
 * Emily Prentiss and Derek Morgan
 * Sydney Manning
 * Aaron Hotchner, David Rossi, Spencer Reid, and several SWAT agents

Real-Life Comparison
The episode was inspired by the film Natural Born Killers, which is also about a pair of lovers who go on a killing spree together. Like the female of that couple, Sydney was also molested as a child. The movie, in turn, was inspired by the two-month killing spree of Charles Starkweather (whose middle name actually was Raymond) and his then-underage girlfriend, Caril Ann Fugate.