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I love you, Ray.
Sydney to Ray

Sydney "Syd" Donovan (née Manning) was a psychopathic spree killer, thrill killer, arsonist, and robber who murdered several people along with her lover Raymond Donovan. They appeared in the Season Six episode of Criminal Minds, "The Thirteenth Step".


Sydney was born on October 14, 1985, in Spokane, Washington, but her family later moved to North Dakota. During her childhood, she was frequently molested by her father Gary, who owned a gas station, where some of the molestation took place. Whenever she was molested at the gas station, Sydney would always hope to somehow be rescued when a customer came by, but it never happened. Eventually, her father's sexual abuse was discovered and she was taken away from him by Family Services on August 23, 2006, and placed her in foster care in Billings, Montana. On April 12, 2007, Sydney received a citation for driving under the influence and had to pay a fine but didn't serve any jail time. On December 20, 2009, she caused a hit-and-run accident while under the influence of alcohol and heroin and was subsequently sentenced to four years of mandatory rehabilitation after being paroled. While at an Alcoholics Anonymous meeting, Sydney fell in love with Ray Donovan after she heard him open up about his troubled past, in which he was molested by his own father, Paul. However, she realized that he had feelings for his ex-girlfriend Amy Wichowsky. Out of jealousy, she gave her a mixture of alcohol and heroin, indirectly causing her to fatally overdose on it. Afterward, she and Ray started going out.

The Thirteenth Step[]

See section on the Ray Donovan and Sydney Manning article

Modus Operandi[]

Sydney used one or two revolvers for most of her killings, though her first two victims with Ray were killed by being savagely beaten to death. Additionally, during the Billings gas station massacre, she used at least one pump-action shotgun, one of the victims was bludgeoned with a baseball bat before being shot at point-blank range, the clerk was bludgeoned and sodomized with a tire iron before being shot to death, and another victim was unintentionally finished off by a gas explosion. She also indirectly killed Amy Wichowsky by giving her heroin that she mixed with alcohol in a fatal mixture.

Known Victims[]

  • December 20, 2009, unspecified location: An unspecified hit-and-run accident
  • March 13, 2010, Jamestown, North Dakota: Amy Wichowsky (Raymond's ex-girlfriend; killed by an overdose of drugs and alcohol)
  • 2011:
    • January 2, Jamestown, North Dakota: N. Apu (first name unrevealed; robbed and beaten)
    • January 4, Bowman, North Dakota: Unnamed convenience store clerk (beaten and presumably robbed)
    • January 8, Miles City, Montana: Six people killed at a local gas station. Known victims killed by her are:
      • An unnamed man (shot at least three times)
      • An unnamed man (shot three times)
    • January 8-9, Billings, Montana: Eight people killed at a local gas station. Known victims killed by her are:
      • The unnamed owner (shot at least twice in the chest)
      • An unnamed man (killed by a gas explosion)
      • An unnamed man (fatally bludgeoned with a baseball bat, then shot at point-blank range post-mortem)
      • An unnamed teenager or young man (shot with a shotgun)
    • January 9, Helena, Montana: At least eight people killed at an Alcoholics Anonymous meeting place. Known victims attacked by her are:
      • Jason (the man hitting on her; pistol-whipped on the forehead by her, then killed by Ray)
      • An unnamed victim (shot repeatedly by her and Ray)
    • January 10:
      • Unspecified location in Idaho: Paul Donovan and his unnamed wife (Ray's parents; both held hostage):
        • Paul Donovan (was later shot in the head execution-style)
        • Ray's unnamed mother (held at gunpoint)
      • Spokane, Washington: The attack at Gary Manning's gas station:
        • Gary Manning and his daughter Heather (her 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; got into a gunfight with them while trying to escape)



  1. Though she is stated to have married Ray right after the Miles City gas station massacre, Sydney is commonly referred to by her birth name, also being credited in the episode as such.