The Cowboy was a bounty hunter who specialized in extralegal skiptracing. He was notorious for wearing a large, black cowboy hat, giving him his name.
The Cowboy is approached by Raymond Reddington in his car, who hires him to find out where Lucy Brooks has been and what she has been doing. After reluctantly agreeing, the bounty hunter goes through her apartment and finds fake identities, a flash drive and numerous trips to places such as D.C, Miami and Havana, Cuba; the same locations Red has been at for the past 6 months. He deduces that Brooks is either after many small, quick targets or is preparing for one big target.
He meets with Red again, showing him what he found in the flash drive; pictures of Red and Elizabeth Keen, offering to take her out. Red says no, that he wants to see how her plan "plays out".
The Cowboy tails Tom Keen and Lucy to Tom's safehouse, where Tom keeps a record of Liz's work. He shows Red pictures of them together and tells him that if he wants him to bring her in, he will charge Red double. As The Cowboy closes in to stab Lucy and take her, Tom walks up behind the bounty hunter and subdues him.
The Cowboy is later tied to a chair while Tom argues with Lucy about what to do with him and for whom he is working. He tries to convince her that Tom will kill her since she has become too intrusive into his mission, but is ignored. After Lucy is suffocated by Tom, The Cowboy is shot by Tom and later buried alongside Lucy. Dembe Zuma later tells Red that he was unable to locate The Cowboy.
Kathryn Nemec shows Red and Dembe the bodies of both Lucy and the Cowboy in the forest where she found them, casting suspicion on Tom.
- What is the history between The Cowboy and Raymond Reddington? It was implied that a previous deal ended in mutual anger.