His name is first mentioned in the episode Ghost in This House by Zach who tells Deacon that Jessie Caine was previously married to him. She later reveals that he was abusive to both her and their son and had an affair with her former assistant who was also her best friend.
He first appears in the episode The Night Before (Life Goes On) when he approaches his ex-wife at a charity fundraiser that Deacon is attending. The latter notices how uncomfortable she is around him, especially when he talks about their son. After Deacon leaves following Rayna's jacket being auctioned off, Brad sends Jessie a text, poking fun at his stepfather issues.
He shows up unannounced at Jessie's house looking for Jake only to be told that the latter is spending the night at a friend's house. Jeff does not take too kindly to the news, mentioning the court order and tells Jessie to bring Jake home so that he can take care of him.
He meets with Deacon and announces his intention to buy him out but Deacon is not interested. He later meets with Zach and suggests they team up to take over Highway 65.
He meets both men again at a New Year's Eve function in the final season premiere and derides both of them - Deacon for showing up alone and Zach for, in his eyes, not being as wealthy as him. When he leaves, Zach tells Deacon how much he hates Brad, a feeling that Deacon shares.
In the episode Beneath Still Waters, he sees Will, Avery, Gunnar and Alannah perform and then gives the latter his business card, saying that she does not need boys around her and that she is wasting her talent with them.
After seeing Daphne Conrad performing at her school talent show in the episode Can't Help But Wonder Where I'm Bound, he takes a special interest in her while feigning interest in his son's rapping skills at the same show.
When he sees Daphne audition for his new reality talent show Nashville's Next Star in the episode Sometimes You Just Can't Win, he mentions that she is Rayna Jaymes' daughter. Jessie later confronts him after Jake reveals to his mother that Brad intends on sending him away to boarding school and refuses to leave his room or talk to her. When Brad shows up, a fight breaks out which is broken up by Deacon as a shocked Jessie looks on.