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Raymond Donovan and Sydney Manning

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Donovan and Manning
Name Raymond "Ray" Donovan
Sydney "Syd" Manning
Type Killer Couple
Country of Origin North Dakota, U.S.
Area of Operation North and northwestern U.S.
Affiliation Each other
No. of Mutual Victims 26+ killed
2 attempted
2 hostages
Appx no. of Members 2 (both deceased)
First Appearance The Thirteenth Step

"Till death do us part."

Raymond "Ray" Donovan and Sydney "Syd" Manning were two young lovers who went on a killing spree together in Season Six of Criminal Minds.


See sections on the Raymond Donovan and Sydney Manning pages

The Thirteenth StepEdit

In the beginning of the episode, 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, stating that she doesn't want to be "a possession". When the clerk begins making cracks about marriage, including that Sydney would eventually get fat, Ray pulls out a handgun and starts firing at him while Sydney draws a revolver and shoots at customers. Immediately afterwards, the pair get a wedding license and get married. The attack, which leaves everyone inside the building dead, leads to the BAU being called in. As the team is being briefed, Ray and Sydney have already started another mass 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 in a stolen car, laughing and declaring their love for each other. Upon investigating the crime scene, Morgan 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 soon after the Billings massacre 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, to which Sydney replies, "Exactly the way we've spent the last twenty-four hours." Ray, feeling some guilt over last night's excessive drinking, later decides to attend an Alcoholic Anonymous meeting in Helena, Montana, while Sydney waits in the car outside 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 once molested him when he was seven years old. When he is finished with his story and another attendant asks him whether he has done step seven of the recovery process (admitting his shortcomings), Ray becomes defensive, stating that it wasn't his fault that his father started molesting him. When the attendant tells him that his drinking problem will continue if he doesn't let the molestation go, an agitated Ray pulls out his gun and shoots the man repeatedly. Sydney, having pistol-whipped the man outside as they were engaged in foreplay, walks in carrying a pair of revolvers and fires at the other attendants, being quickly joined by Ray. As they leave, Ray shoots and kills the man who tried to have sex with Sydney, before the two steal another car and flee.

While the BAU give the profile to investigators, Sydney suggests that they do step nine, make amends, and take it up with the source of all their rage: their fathers, starting with Ray's. After tracking down Ray's parents in Idaho, they force Ray's father, Paul, inside his trailer home at gunpoint. After holding his mother hostage as well, Ray loads a revolver with a single bullet, spinning the cylinder afterwards. He then holds it to his father Paul's head and tries to make him confess to molesting him, pulling the trigger every time he denies it, coming up with blanks every time. Paul consistently and determinedly denies Ray's accusations every time. Eventually, Sydney, growing impatient, finishes a bottle of alcohol, drops it, and passively kills Paul herself. The two then leave while Ray angrily yells at Sydney for killing his father before he could, shouting that it was "his thing", not hers. Soon after the latest shooting, the BAU, having already identified Ray as one of the unsubs, realize the pair's newest plan and manage to identify Sydney as the other unsub. The team then heads to find Sydney's father, knowing that he would be the next target.

After driving away from the house, Ray pulls over by the road and starts fighting with Sydney, who tries to get him to hit her. As he holds her in a choke grip against a tree, she starts unbuttoning his pants. They quickly make up and start kissing. They then drive to Spokane, Washington, make their way to the gas station owned by Sydney's father Gary and hold him at gunpoint, forcing him to also go through step nine and confess to molesting Sydney. When he denies it, she angrily pistol-whips him to the floor. When he apologizes and claims to have found God and changed, Ray gets frustrated to the point where he starts punching and pistol-whipping him while Sydney spurs him on. Gary's 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 that they will take her away, believing her father to have molested Heather as well. As they step outside with her, Prentiss and Morgan arrive, having tracked them down. Shots ring out as Prentiss takes cover and Morgan fires back at them, one of his bullets ripping through Sydney's shoulder. As Sydney is screaming in pain, Ray drags her back into the store while Morgan is still shooting at them, and they are forced to remain where they are due to Sydney's continuous loss of blood.

When the rest of the BAU and SWAT arrive, Hotch calls Ray, who demands to talk to Morgan since he was the one who wounded Sydney. Ray demands a car, tickets to Aruba, gauze for Sydney's wound, and alcohol. After Morgan 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, Morgan tells him that heroin was found in her system; though she had never used heroin before that day, Sydney regularly used it in combination with alcohol, which is what killed Amy. As Ray begins to realize that Morgan 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 of a window with an SUV with Sydney's body in the passenger seat, firing indiscriminately at the police and hallucinating about Sydney, before eventually being shot to death by Morgan, the BAU, and local police.

Modus OperandiEdit

Ray and Sydney used firearms for most of their killings, though their first two mutual victims were killed by savage beatings. Ray's handgun of choice was a semiautomatic Beretta 92F while Sydney used one or more revolvers. Both also used at least one pump-action shotgun. Their favorite target was gas stations (the same kind of business Sydney's father owned), but during their last mass shooting, they targeted an Alcoholics Anonymous meeting, which appeared to have been merely caused by Ray snapping. Though the first mass shooting was apparently a spur-of-the-moment decision, the second was more planned, as they forced several people inside the station and then sealed the entrance with a padlock before they started shooting. During that attack, they used a crowbar and a baseball bat to kill some targets and also left rice on the floor as a reference to their recent marriage. They also bludgeoned and sodomized the clerk with a tire iron before shooting him to death. Additionally, one customer was left alive to be finished off by the explosion Sydney caused, but that appears to be unintentional, as Ray was seen repeatedly shooting him in the back earlier. The two then targeted their fathers under the delusion that they needed to make amends.


The unsubs are a couple, late teens to mid-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 their 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. From this, it is believed that one of them is a sociopath while the other is a psychopath. Though the definitions of both are similar in terms of pathology, a sociopath is less likely to engage in criminal activity and can be led by someone dominant, while a psychopath 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 very likely that she was the psychopathic partner while he was the sociopathic partner.

Real-Life ComparisonEdit

The episode was inspired by the film Natural Born Killers, which is also about a pair of young 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. They are also extremely similar to the infamous Bonnie and Clyde, who too were a murderous couple that committed several notable robberies, and whose crime spree ended in a massive hail of gunfire that killed at least one of the members.

Mutual VictimsEdit

  • 2011:
    • January 2, Jamestown, North Dakota: N. Apu[1] (full first name unrevealed; convenience store clerk; robbed and beaten)
    • January 4, Bowman, North Dakota: Unnamed convenience store clerk (beaten like the previous victim and presumably robbed)
    • January 8, Miles City, Montana: Six people killed at a local gas station. They are:
      • The unnamed clerk (shot repeatedly by Ray)
      • Five other unnamed people
    • January 8-9, Billings, Montana: Eight people killed at a local gas station. They are:
      • The unnamed clerk (bludgeoned and sodomized with a tire iron, then shot)
      • The unnamed owner (shot at least twice in the chest by Sydney)
      • An unnamed man (shot repeatedly in the back by Ray; survived, but was killed by the explosion Sydney caused)
      • An unnamed man (fatally bludgeoned with a crowbar, then shot at point-blank range post-mortem by Ray)
      • An unnamed man (fatally bludgeoned with a baseball bat, then shot at point-blank range post-mortem by Sydney)
      • An unnamed victim (survived the massacre, but most likely died at the hospital)[2]
      • Two other unnamed people
    • January 9, Helena, Montana:
      • At least seven people killed at an Alcoholics Anonymous meeting place. They are:
        • Tim (the first AA attendant killed; shot at least twice by Ray)
        • At least six other unnamed attendants
      • Jason (the man hitting on Sydney; shot in the head by Ray right after the above shooting)
    • January 10:
      • Unspecified location in Idaho: Paul Donovan and his unnamed wife (Ray's parents; both held hostage):
        • Paul Donovan (was later executed by Sydney)
        • Ray's unnamed mother (held at gunpoint)
      • Spokane, Washington: The attack at Gary Manning's gas station:
        • Gary Manning and his daughter Heather (Sydney's father and half-sister, respectively):
          • Gary Manning (beaten by both and shot execution-style by Ray)
          • Heather Manning (intended to abduct; later held hostage by them)
        • Emily Prentiss and Derek Morgan (attempted; both got into a gunfight with them while trying to escape)

Appearances Edit

References Edit

  1. Obviously an off-color reference to the popular animated sitcom The Simpsons, including one of the show's many characters, Apu Nahasapeemapetilon, who too was a convenience store clerk of Indian descent (Garcia's rap sheet shows N. Apu to be of Indian descent)
  2. A Billings police detective told the BAU, "One of the vic[tim]s said the shooters were a male and a female", suggesting that a victim survived, but as there are no injuries confirmed in Ray and Sydney's attacks, it's possible that he or she died of the sustained injuries at a hospital

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