Enough's enough, baby.

Raymond "Ray" Donovan was a sociopathic spree killer, thrill killer, arsonist, and robber who murdered several people with his lover Sydney Manning in the Season Six episode "The Thirteenth Step".


Ray was born around 1984 in Devils Lake, North Dakota. When he was seven years old, he was molested by his alcoholic father Paul, who was presumably drunk at the time. He had been traumatized by the incident ever since. At the age of ten, he was placed in foster care due to drug problems, but 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 the influence. On February 13, 2010, his girlfriend, an alcoholic named Amy Wichowsky, filed a restraining order against him. Ray later started going to Alcoholics Anonymous meetings to get rid of his addictions; at one of those meetings, he met Sydney Manning, who had a similar background of substance abuse and molestation by her father. Sydney fell in love with him, but Ray still had feelings for Amy. When she found out, Sydney murdered Amy by giving her a mixture of alcohol and heroin which she overdosed on. With Amy dead, Ray started going out with Sydney, believing Amy had accidentally overdosed on alcohol and PCP.

The Thirteenth Step

See section on the Ray Donovan and Sydney Manning article

Modus Operandi

Ray used a Beretta 92FS semi-automatic pistol for most of his killings, though his first two victims with Sydney were killed by savage beatings. Additionally, during the Billings gas station massacre, he used at least one pump-action shotgun, one of the victims was bludgeoned with a crowbar before being shot at point-blank range, and the clerk was bludgeoned and sodomized with a tire iron before being shot to death by Sydney. When he killed Sydney, he manually strangled her to death.

Known Victims

  • 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 him are:
      • The unnamed clerk (shot repeatedly)
    • January 8-9, Billings, Montana: Eight people killed at a local gas station. Known victims attacked by him are:
      • An unnamed man (shot repeatedly in the back; killed by a gas explosion caused by Sydney)
      • An unnamed man (fatally bludgeoned with a crowbar, then shot at point-blank range post-mortem)
      • An unnamed woman (shot with a shotgun)
    • January 9, Helena, Montana: At least eight people killed at an Alcoholics Anonymous meeting place. Known victims killed by him are:
      • Tim (the first AA member killed; shot repeatedly)
      • An unnamed woman (shot in the back)
      • Jason (the man hitting on Sydney; pistol-whipped on the forehead by Sydney, then shot in the forehead by him)
      • An unnamed victim (shot repeatedly by him and Sydney)
    • January 10:
      • Unspecified location in Idaho: Paul Donovan and his unnamed wife (his parents; both held hostage):
        • Paul Donovan (held at gunpoint and played a game of Russian Rulette with him; was later executed by Sydney)
        • His unnamed mother (held at gunpoint)
      • Unspecified location: Sydney Manning (his wife; assaulted)
      • 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 him)
          • 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)
        • Sydney Manning (manually strangled to death)
        • Shot at the following:


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