The Undertaker: Unwilling to Retire, Roberts, & Tattoo Anecdote with McMahon

“My transition…I knew my time had come. But I wasn’t ready for it to come."

by Sead Dedovic
The Undertaker: Unwilling to Retire, Roberts, & Tattoo Anecdote with McMahon
© JP Yim/Getty Images Entertainment

Retiring is never an easy thing. When you've been on the big stage for years and have had great successes behind you, deciding to retire can be very difficult. 

The Undertaker had big dilemmas about whether to end his career and realized it was the best decision for him. 

During his "Six Feet Under with Mark Calaway," The Undertaker reflected on one of the toughest decisions in his life. 

Despite knowing that his body couldn't endure the same demands anymore or perform at his best, The Undertaker had tough days contemplating retirement.

This once brilliant wrestler made his debut in the WWF back in the 1990s, where he secured a victory over Mario Mancini. After showing immediate potential for great things, his career only went up. The Undertaker became one of the best wrestlers.

The Undertaker emphasized that he had always had a huge passion for wrestling, and he had spent almost his entire life doing it. When you end your career, there's a big void left. The Undertaker was thinking about how he could fill that void.

“My transition…I knew my time had come. But I wasn’t ready for it to come. I just knew that my body couldn’t deliver what my mind and my heart wanted to give the fans and it was kind of difficult. You have to remember that for over half of my life, being in the ring is what I did, and then it’s not there anymore. That does, it leaves a huge void in you because you’re trying to fill that void, which was a passion. You’re trying to find out what that next passion is and what it is that you’re gonna sink your teeth into and there just may not be something that will ever refill that void.”- The Undertaker said, as quoted by

Even after retiring in 2020, The Undertaker still finds it challenging to fully transition away from wrestling. He admits that while watching wrestling at home, he tends to analyze it more critically, but when he's at a live event, he often feels the urge to return to the ring. 

This internal conflict between his retired status and his former wrestling career continues to affect him, and he hopes to eventually overcome it.

It's incredible how much the sport you engage in becomes a part of you, and it's hard to imagine life without it. Many athletes express the same sentiment.

After ending a career, there's a significant void that you try to fill. Many choose various ways to do so, but often without success.

The Undertaker and Jake Roberts: Roberts helped me through my career

The Undertaker also reflected on Jake Roberts, his close friend, who had helped him throughout his career. This Hall of Famer highlighted that he had the opportunity to learn a lot from his colleague. The Undertaker often traveled with Roberts and picked up some things from him. 

Although many consider these to be mostly positive, The Undertaker confirmed that he also developed many bad habits from Jake. 

Jake Roberts
Jake Roberts© Larry Busacca / Getty Images Entertainment

Nevertheless, this Hall of Famer regards Roberts as a wrestling genius because of everything he has accomplished in his career. 

The once-brilliant wrestler also revealed the advice Roberts gave him before matches. Jake often emphasized: "Your match starts as soon as you walk through that curtain. It doesn’t start at ding ding ding; the match starts as soon as you come out of Gorilla Position."

The Undertaker and Vice McMahon

The Undertaker and Vince McMahon generally had a great relationship, considering they worked together for years. However, there were also times when The Undertaker would anger McMahon with certain actions. During his podcast, The Undertaker recalled one of these moments.

WWE legend The Undertaker talked about how his boss, Vince McMahon, got mad at him for getting tattoos without asking. He explained that even though McMahon didn't like it at first, the tattoos actually made his character better.  McMahon was angry, and emphasized that The Undertaker should not do such things. The WWE boss expected The Undertaker to consult with him before making a decision.

Vince McMahon
Vince McMahon© Ethan Miller/Getty Images

He also mentioned that he wasn't happy with one tattoo he got because it didn't turn out how he wanted it to. So, he decided not to finish it. 

The Undertaker, like many wrestlers, made huge mistakes in the early stages of his career due to inexperience. However, over the years, he became much more mature, and McMahon had increasingly more respect for him. It's not surprising why McMahon respected him. The Undertaker was one of the main faces of the company for years.

The Undertaker