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Trust Me: Jake ‘The Snake’ Roberts Return to the Darkside

Posted: Jun 9th 2026 By: Brian Damage - RingTheDamnBell.com

It was always going to take a big angle to turn Jake ‘the snake’ Roberts, one of the WWF’s top babyfaces at the beginning of the 90s heel. But what an angle it was. Today, we ‘trust’ Brian to take us through the story about how Roberts turned to the dark side in 1992.

It began with two simple words: Trust Me. It would become the words that would turn the World Wrestling Federation on its ear both literally and figuratively. The year was 1991 and Jake the Snake Roberts was one of the top babyfaces in all of the WWF right behind Hulk Hogan and the Ultimate Warrior. Roberts had just completed a feud with the Earthquake in which Earthquake “killed” Jake’s pet snake Damien. After the death of Damien, Roberts began showing more of a dark side to his gimmick. His promos were darker in tone and he seemed to be evolving as a character. While Jake was exacting his revenge on Earthquake, the Ultimate Warrior was beginning a feud with the Undertaker. It all began when the Dead Man attacked Warrior while he was a guest on Paul Bearer’s Funeral Parlor talk show. Taker would stuff the Warrior inside a coffin and left him for dead as road agents and officials tried to open the airtight casket.

Jake Roberts would then be a guest on Bearer’s talk show and offer to “teach” the Ultimate Warrior the ways of the darkness to combat the Undertaker. The Ultimate Warrior begrudgingly accepted the offer and Jake simply told Warrior to trust him. Roberts would then put the Warrior through a series of tests that would push the Ultimate Warrior to confront his fears. These tests were supposed to make the Warrior stronger mentally to fight such a dark and ominous figure in the Undertaker. The first test had Jake Roberts convince a very fearful Warrior to climb back into a coffin. Jake Roberts offered the Warrior an opportunity to walk away but the Warrior agreed to go through with it. Warrior sat in the coffin and despite his fears, Roberts urged him to trust him. He closed the coffin with Warrior inside and began tutoring him on how to survive inside of it.

The second test found Jake and the Warrior in an undisclosed cemetery. Jake made Warrior dig a deep ditch. Warrior would discover a skull and started to freak out but once again Jake would comfort him and urging him to trust him. Jake would then bury the Ultimate Warrior in the ditch, leaving only his head above the dirt. Jake then placed the skull right in front of Warrior to just stare at it and embrace his deepest fears. The third and final test had Jake take the Ultimate Warrior to some sort of dark basement and told the Warrior to enter this room and open the box in the middle of the room. This was his final test and it would reveal the keys to defeating the Undertaker and conquering his own fears. Once the Warrior entered the room, he was greeted by seemingly hundreds of different snakes. As Roberts urged Warrior to just move forward and open the box, the Warrior was navigating through all these snakes. In reality, the Warrior was fearful of the snakes. Behind the scenes, Roberts told the Ultimate Warrior how to move in the room without the snakes legitimately biting him. Roberts told Warrior to shuffle his feet but Warrior began to really panic and began quickly stepping through the snakes, getting bit several times in the process.

Back to the actual segment, Warrior reached the box in the middle of the room. When he opened the box, a king cobra popped out staring him in the face. The poisonous cobra bit the Warrior and Roberts continued to tell Warrior to fight his fears. The poison started to make the Warrior fade into unconsciousness. Warrior was able to break the locked door down and standing in front of him was none other than the Undertaker and Paul Bearer. Roberts would ask Warrior to reach out and take his hand for help but Roberts pulled away and began to laugh. He then told the Warrior “never trust a snake.” The heel turn was complete, Jake the Snake was in cahoots with the Undertaker all along.

The backstory to all of this was Jake Roberts was legitimately unhappy as a baby face behind the likes of Warrior and Hulk Hogan. For months, Roberts approached Vince McMahon about turning him back to a heel. McMahon was never completely sold on having a popular wrestler like Jake turn heel but Roberts eventually convinced him. With McMahon on board, Roberts came up with the idea of how to turn heel. The only thing Roberts had to do with Vince’s request was to ask the Ultimate Warrior himself to go through with it.

Jake Roberts thought McMahon was joking but, alas, he was very serious. The Warrior was a top star and apparently required all storylines go through him first. When Roberts called the Warrior about the angle, Warrior initially gave Jake a very hard time. In the end, though, Roberts was extremely persuasive and convinced him to the idea. Sadly, the feud never culminated in a match because the Warrior would have a dispute with McMahon over money he felt was owed to him and he was suspended. The Ultimate Warrior rejected the suspension and decided to walk away instead. The WWF had no choice but to fire the Ultimate Warrior. The decision left Jake the Snake Roberts without a feud. All of that for nothing. Looking back, it was one of the most daring the WWF had been during that era in its history. Who knows how the Ultimate Warrior/ Jake Roberts feud would have turned out? All we have are the vignettes and trust the WWF would have delivered on it.