This article contains plot spoilers for the 2017 series of Twin Peaks.
At dinner with Cooper, Darya, and Jack, he and Cooper discussed the latter's alleged worry about the next day. They further discussed information that Ray was to receive from the secretary to William Hastings.
Ray did not show up for a planned meeting with Cooper, as he had been arrested and incarcerated in federal prison in South Dakota for carrying guns over the state line. He called Darya and they discussed their job from to kill Cooper, having received a message from Phillip Jeffries.
After Cooper deactivated three tracking devices on the car, they went to a secluded area. Cooper demanded the information and tried to shoot Ray, but Ray had already unloaded his gun. He then shot Cooper and saw shadowy men gathering around him and tearing at him, revealing to him the face of BOB.
Cooper tracked Ray to The Farm, where he arm-wrestled and killed its leader, Renzo before demanding to be alone with him. Ray was shot in the leg by Cooper and he told him that Phillip Jeffries was hired Ray and Darya to kill Cooper and was to place a ring on Cooper after killing him. Cooper had Ray put on the ring and hand over the coordinates. Ray was asked about Jeffries' whereabouts and Ray said he was at "The Dutchman's" before Cooper shot him in the head. The ring disappeared from Ray's body, which then followed suit, appearing in a red room.