This article contains spoilers from the 2017 series of Twin Peaks. If you are not up-to-date with the aforementioned television program, it is strongly recommended that you do not read this article.
Ray Monroe is an associate of Cooper.
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 a long-haired man.