Undertaker and Sting under the microscope of legendary J.J. Dillon

The Undertaker has wrestled against so many icons. The list of competitors The Phenom has faced is amazing. Hulk Hogan, Ric Flair, Shawn Michaels, Bret Hart and Mick Foley are just some superstars who have felt his in-ring wrath.

As Undertaker prepares for the glory of being inducted into the WWE Hall of Fame, fans still talk about one opponent he never squared off against. It's the match that never was but we all wanted to see. That match would have been Undertaker vs. The Icon Sting. It has been put into the "Dream Match" category and it should have happened. They did face each other once, but The Undertaker was a different person, a different character.

I looked through my extensive files and found that NWA World Champion Sting wrestled "Mean" Mark Callous, managed by Paul Heyman in Greensboro, North Carolina, in 1990. Sting was successful in defending his title. Still, fans continue to wonder what would have happened if Sting and Mark, as The Undertaker, actually clashed in their respective primes.

In a conversation with Sting several years ago, he told me:

"I brought it up a few times. I wanted it to happen. I thought even a cinematic match with him would have worked. It just never got done. It never materialized and I can't put my finger on any real reason it didn't take place."

Undertaker, towards the end of his career, acknowledged the desires of fans and recognized that a match against Sting would've been a high-profile affair. However, The Phenom has admitted in several interviews that the match would've worked better in the '90s or 2000s as opposed to when both he and Sting were already in the advanced stages of their careers.

Would this match have been something the WWE Universe really wanted? Who would've won? What would've happened to the loser?

I had an opportunity today to ask these very questions to the legendary J.J. Dillon. He was a wrestler, manager, the Head of WWE Talent Relations for many years, and a booker for many companies. He had a booker's point of view regarding this particular "Dream Match". Here's what he said:

"Throughout the years fans have loved to speculate about dream matches like Sting against Undertaker. In the mind of us in the business we have a different take. Think about this. You really have to dissect a match and break it into pieces.

"The main object is to move a step further and figure out what will happen after the match ends. Will the fans be satisfied and what happens to the loser? Does he lose favor with the fans or what? In my mind it's best to let dream matches be just that. Let the fans speculate as the actual match may not be what they are actually expecting to see. Sometimes the fantasy in their minds of the match may be better than the reality of the match."

I went on to ask J.J. about Undertaker going into the WWE Hall of Fame this year. (Sting was inducted in 2016.)

"Undertaker, he's an original, one of a kind," he said. "In ring excellence and he always gave fans exactly what they wanted to see. There were two spots they clamored for in each match. One was when Undertaker was laid out by an opponent and laying there on the mat. Then there would be that five to ten second delay and he would sit up, the 'Dead Man' coming back to life and the crowd would erupt with an amazing reaction. Then he would walk the ropes like he was on a tightrope from turnbuckle to turnbuckle and the fans would go bananas again! You cannot create something like that. It's a spontaneous reaction by the fans.

"Personally Undertaker is a great guy. He worked with all the superstars in the industry -- except Sting of course. Success never changed him. He's still the nicest person to everyone he comes in contact with as well. He mentors young wrestlers when he's around. There is no one like him."

I did press the original issue of Sting vs. Undertaker and asked if he had booked the match, what would the finish have been?

"That's easy," J.J. said. "I will make it a 60 minute time limit match and of course, I'll take the easy way out and make it a time limit draw!"