As Sting prepares for his final professional match at AEW Revolution, it's hard for some fans not to think about the one that got away, “The Icon” versus The Undertaker at the biggest show on the WWE calendar, WrestleMania.

On paper, the story sort of wrote itself; in January of 2014, when Sting's TNA contract came to an end, Taker was still going strong, with his “Streak” still a few months away from being broken by Brock Lesnar. Assuming the promotion kept true to their plans to give Lesnar the ultimate rub, the duo could have headed into a future match at WrestleMania 32 or otherwise without any pre-existing biases, leading to the sort of “Clash of the Titans” match where either man could come out on top and the excitement surrounding the showdown would have been at an all-time high.

Unfortunately, Sting never made it to WrestleMania 32, as, after taking a brutal Buckle Bomb from Seth Rollins at Night of Champions 2015, he was forced to retire from WWE and wrestling as a whole shortly thereafter, leading many fans to assume that he'd never wrestle again… at least until AEW Revolution 2021, when he made his triumphant return in a tag team match with Darby Allin against Team Taz.

So naturally, with Sting's final match rapidly approaching, Shakiel Mahjouri of CBS Sports asked “The Icon” about the prospects of wrestling The Undertaker during his WWE run, to which Sting had some very interesting insight into what could have been.

“I think if it was done right, it could have been a night, for sure, everyone would remember and never forget. They would be talking about it to this day. But it just was not going to happen. I thought, ‘Well, maybe if I get my foot in the door, we'll see what happens.' So I got my foot in the door. We did a WrestleMania with Triple H, and then Vince [Vince McMahon] called and said, ‘Hey, I want you to have a world title match with Seth. Would you be willing to do that?' ‘Yeah, I'd be willing to do that.' Still, in hopes that somehow I could get in there with Taker,” Sting told CBS Sports.

“I had so many ideas over the years. A lot of times, smoke and mirrors aren't good things. But in our situation, I think with his gimmick and the mystiques of his character and mine, we couldn't have enough smoke and mirrors. I think it definitely would have been a night that people remembered. Man, I would have loved to have seen that. If I could have had that match alone, I would have been great. I wouldn't have had to do anything else.”

Gosh, could you even imagine what Sting and The Undertaker could have cooked up in WWE had the duo both remained healthy and active in WWE? While it's unlikely the match would have been “cinematic,” as that was very rare in the mid-2010s, the idea of using some smoke and gimmicks, maybe a hybrid Street Fight/Coffin match, could have produced the sort of effort that would have given fans all the spots they expected and even some interesting ones they couldn't have imagined in an effort worthy of all-time consideration. *sigh* oh well, at least Undertaker stuck his landing in the Boneyard match, and Sting will likely follow suit with a main event match at AEW Revolution.

Kane appreciates his experiences working with Sting.

While Sting may have never been afforded a chance to work with The Undertaker in WWE – technically, he worked a match against “Mean Mark” at WCW back in 1990 on a house show – “The Icon” did work a match against his “Brother of Destruction,” Kane on WCW Saturday Night in 1993, when he was then known as “Bruiser Mastino.”

Reflecting on his experience working with Sting in the 1990s in an interview with David Gornowski, Kane celebrated his experience working with Sting, as he loved getting in the ring with one of the “greatest Superstars of all time.”

“I didn't get to work with him that much. I was actually one match with him in WCW. I had one match in WCW and that was with Sting. That was very early in my career. Then, he came to WWE late in his career, he had already retired and come back and that was also late in my career, but Steve is a really great guy. From my interactions with him, I can't say enough about the human being. He's always treated me very well. He was also one of my favorites back when I was younger, so it's pretty cool when you get to work with the people he watched on TV and go, ‘Wow, this is really awesome! I'm in the ring with Sting. How cool is that?'” Kane told David Gornowski via Fightful.

“When he was in his prime, he was a great athlete. He could move. People forget he's not a small guy. He's probably 6'3 and 260 lb, but he could do all the things you think of a much smaller person doing. So, he's an impressive athlete, and frankly, one of the biggest Superstars of all time, especially in WCW.”

Jeez, now fans have to imagine what a match between Kane and Sting would have looked like in their fully formed characters, a match that probably would have happened if a match against The Undertaker had gone over like gangbusters in 2015/2016. While Seth Rollins will likely go down as an all-time WWE performer, that Buckle Bomb created one of the greatest “What Ifs” in professional wrestling history.