Randy Orton has carved out one of the greatest all-time careers in the history of the WWE, starting in 2001 when he signed a developmental deal with OVW.

Being the former Head of Talent Relations for WWE and the person who signed Orton to his original WWE contract, Jim Ross spoke about having to convince Vince McMahon to hire the third generation superstar on the latest episode of the Grilling JR Podcast. JR mentioned how McMahon had an issue with Orton leaving the Marines before pursuing wrestling, and wasn’t interested in signing the 14-time World Champion at that time.

“Every recruiting story is different,” Ross mentioned. “I had a hard sell to get Randy Orton hired because of his negative exit from the Marines, and Vince, being a strong patriot, didn’t like how that worked out with Randy in the military. I said, ‘Didn’t you get a second chance, [Vince]? Well, what’s the difference with this kid? He’s third generation. If he hits, look what we have. If he doesn’t hit, I can get rid of him in 90 days notice. What do we have to lose?'”

“He’s going to end his career as one of the greatest talents. Hall of Famer, no doubt, but also going to be regarded by his peers as one of the greatest in-ring workers. It worked out well.”

While speaking on the podcast, Ross covered the infamous Hulk Hogan heel turn, where one of the biggest babyfaces in the history of wrestling transitioned into “Hollywood” Hulk Hogan by joining the nWo at Bash at the Beach 1996. The WWE Hall of Famer revealed that although Hogan’s heel turn happened in WCW, it would’ve been difficult for him to envision Vince McMahon changing his mind and turning Hogan heel in WWE.

“Vince would’ve had to have been really convinced,” Ross said. “Vince was a Hoganite. He helped create the character so he believed Hogan was the supreme, ultimate babyface, and he would’ve had to have a strong argument to change horses. It worked out in WCW the best. I think the fact that we didn’t turn Hogan heel in ’93, and he probably would’ve been a damn good heel in ’93. He could’ve had matches with a lot of guys, but that’s just not what Vince felt. It had to have been a special set of circumstances for [Hogan’s heel turn] to happen.”

Speaking of infamous heel turns that didn’t occur in WWE, John Cena is the poster boy for criticism regarding the star never transitioning back into a heel after his Dr. of Thuganomics gimmick. Ross spoke about WWE never wanting to turn Cena heel on a previous podcast, revealing he was surprised the company never did it.

Someone similar to John Cena would be Roman Reigns, who finally turned heel the past year and has had the best run of his career. Ross spoke about Reigns as well, stating Vince McMahon learned his lesson after not turning Cena heel.

“Vince had the same strong babyface feelings for John Cena that he did for Hulk Hogan,” Ross mentioned. “A superhero. The epitome of a babyface, how a babyface is supposed to be, what he’s supposed to represent. Cena did that well beyond just the lens of the camera. He’s granted more Make-A-Wish requests than anybody in history. He loved Cena’s game plan and how he represented the company.

“Roman Reigns, he found his personality. He discovered his voice so to speak, and I also think Paul Heyman, my old broadcast partner, has been instrumental in the evolution of the Roman Reigns TV persona. You just have to find your voice, find what fits for you. And as we talked about here [with Hogan’s heel turn], it was the right place, right time, right pieces in place, and well executed.”

If you use any of the quotes in this article, please credit Grilling JR with a h/t to Wrestling Inc. for the transcription.