WWE Biggest Missed Opportunities Ever

What's good y'all? It's Boy Ross back at again with another video. So, I'm g check out 10 biggest missed opportunities in WWE. If there's one thing that this company's going to do, they'll set some things up that could be monumental, that could be legendary, that can be uh uh a moment that us fans will appreciate and remember for a very long time, and they can have it all line up, everything just be perfectly, and somehow someway they can find a way to mess it up. We've seen it time and time again. Now, when they get it right, they get it right. But when they actually have the the the steps to make it something better, whether it's a character change, he'll turn, baby face turn, uh uh a moment, someone potentially getting an unexpected win, whatever the case may be. Sometimes things line up for WWE and they'll find a way to mess it up. So, we're going to check out some of these missed opportunities from WWE. Should be an interesting video. I appreciate all love support. Let's get right into the shenanigans. Man, >> at its best, professional wrestling beats all other forms of entertainment, or inspiring moments like Kofi Kingston and Sami Zayn finally laying claim to the WWE Championship will have modern audiences reminiscing for decades to come. This has happened for historical viewers upon reflecting on the glory days of the '90s and the naughties. However, it doesn't always run smoothly, though, especially on the treacherous roads at the top of the mountain in WWE. The industry leader has repeatedly failed to capitalize on key moments, angles, and wrestlers, leaving fans mourning what could have been. Join us now as WrestleMia looks at 10 of the biggest missed opportunities in WWE history. Be sure to subscribe and hit that notification bell for daily wrestling videos. Number 10, The Summer of Punk and Ring of Honor. The summer of punk was crucial in casting a wider spotlight on what was still classed as a niche independent promotion while simultaneously establishing CM Punk as a villain of the piece said unpacking the Ring of Honor World title in a suitcase for Stanford. In WWE, however, the saga fell apart before it even started. Blurring the lines between fiction and reality, the very real situation surrounding CM Punk's contract coming up for renewal was turned into a story line. He was to challenge John Cena for the WWE Championship at Money in the Bank 2011, which just so happened to fall on the exact date of his contract's expiration and took place on Punk's home turf of Chicago. It was almost too good of a story for WWE to tell. The problem is WWE didn't tell the story. CM Punk did win the title that night, but that only came after Cena had been distracted by Vince McMahon and John Lauronitis in his subsequent absence. That only lasted a week. Toss in another questionable defeat of Cena at SummerSlam where John's foot was on the ropes. An idiotic loss to a stupidly irate Triple H at Night of Champions and the general involvement of Kevin Nash and WWE had expertly crafted the first stages of CM Punk's eventual exit from the business. Labeling it as a mess doesn't even touch the sides. They had something there. They legitimately had something special. And there were some great moments that came out of this. But I think ultimately they should have played into it. They should have really played into it. Vince wasn't trying to. But imagine if CM Punk was gone for a while. Imagine he literally took the title and they would allowed him to perform at some of these shows, you know, some of these indie shows or whatnot with the WWE Championship to really sell the story that he took the title and left. They could have really built that up. Was WWE back then going to be willing to work with other companies like that? No. But I think that's just a missed opportunity to really build something up. And then obviously you could have had another WWE uh champion being crowned. And you know, whilst Punk is the real WWE champion out and about, he still works for the company, but they're making it seem as if he doesn't. I think they could have did something there and he came right back. And even though there was some good stuff still, they kind of messed it up. It got muddied very quick. Him losing to Triple H still is to this day makes absolute no sense to me. But hey, it is what it is. Maybe we should do a whole video on this. Number nine, four horse women versus the four horse women. But the movement of UFC's four horse women from the octagon to the squared circle raised many eyebrows in the late 2010s as all eyes were now cast upon a potential showdown with the four horse women of WWE. But the match never materialized despite significant anticipation and the company openly teasing the meeting during the tapings for the 2017 May Young Classic. WWE was unable to move the pieces into place. It was according to Dave Meltzer close to being locked in for Survivor Series in 2018. would have made sense seeing as Becky Lynch and Ronda Rousey were positioned for a singles collision at the event before an injury took Lynch and forced Charlotte Flair into the spot instead and the eight women tag was shelled for good. A lack of experience for two members of the UFC quartet was ultimately ruled as the reason for the match never coming to fruition. While Rousey was tearing it up on Raw and Shaina Basler was doing the same in NXT, Marina Shafir and Jasmine Duke didn't have the same reps as their co-hosts, leading to the WWE's trepidation in placing them opposite Becky, Charlotte Flair, Sasha Banks, and Bailey. >> It would have been a it would have been a big match. >> It would have been a a very big match. Um, obviously, uh, Marina, she's doing her thing in AEW, so, you know, shout out to her. But that I think that would have been a pretty interesting match and it would have been one of the first few times WWE has really centered a show a big PL or pay-per-view at that time Survivor Series around eight women which would have been monumental but uh unfortunately things didn't play out the way you know you know they were expecting to. >> Number eight Shinsuke Nakamura as WWE champion. The WWE is regularly blown hot and cold with Shinsuke Nakamura since he first signed with the company in 2016, but they will never have as good as an opportunity to strike gold with him as they did across 2017 and 2018. promoted to the main roster following WrestleMania 33 propelled Nakamura into the main event picture as he worked a two-pronged WWE championship feud opposite Jinder Mahal that astonishly ended in Shinsuke going Norton two against the Maharaja somehow losing backto-back pay-per-view attractions to the former 3 MB man wasn't a nail in the coffin for Shinsuke's WWE career. He still had a few months left on his shelf life before Vince McMahon swung the axe down for good. A Royal Rumble victory in 2018 meant that Shinsuke would contest AJ Styles for the WWE title at Wrestlemania 34 in a match heavily expected to be on par with the Epic from New Japan's Wrestle Kingdom event in 2016. And although it wasn't on the same level and even though Nakamura lost, all hope still wasn't lost until WWE turned him heel after the match and booked him to become obsessed with whacking people in the balls. That'll literally kill your career. >> Number seven, Ric Flair in the Golden. That's one of those matches that had so much hype behind it and it it just didn't live up to expectations. Um, if there's anybody that maybe could have benefited from a world title run in that period, it definitely could have been Nakamura. The question would have been, would it have been a uh a good title run? That's that's the question you got to ask yourself. Maybe if they would have booked it a certain way, possibly. But that's not what happened. >> Error. While the golden era doesn't receive the same level of internal lording as the attitude or ruthless aggression errors still helped introduce a generation of youngsters to pro wrestling backed by a roster of many of the industry's all-time best. From headline attractions such as Hulk Hogan, Randy Savage, and the Ultimate Warrior to the best inclass midcarters like Bret Hart, Mr. Perfect, and Rody Piper, the era had something for everyone. But it wasn't enough to entice Ric Flair away from WCW. The Nature Boy has talked at length about receiving an offer to jump in 1988 at the time when he was dominating well a new WCW. The topic came up once again during an interview on the Chris Jericho's Rock and Wrestling Ranger Cruz in 2020 where Flair detailed the reasons behind his decision to stay put in Atlanta. They wanted me to come in and wrestle Randy Savage at SummerSlam and I said no, we don't have contracts back then. I just had a deposit on the belt. I was with Anne Anderson and Tully Blanchard and Barry Windham and God we were selling out everywhere. I was happy. It was never about not going up there and having fun because Teddy Beiosi, Rody Piper, I had a lot of friends up there. Bob Orton, too. There were a lot of guys that I was friends with that had already gone there. I just couldn't get myself to leave that circle of friends that I was with. Now, it proved to be the right call for Flair's career as he continued to run high in WCW with his acclaimed series of matches against Ricky Steamboat coming a few months to refuse Vince McMahon's offer. Instead, Rick joined WWF in late ' 91, famously making the move while still in possession of the Big Gold belt for a run that didn't go really anywhere, barring his exceptional 1992 Royal Rumble win. Number six, Ric Flair versus Hulk Hogan. But speaking of that run for the Nature Boy in the WWF, he was reportedly locked in for a Wrestlemania 8 tussle opposite Hulk Hogan, which would have seen Ric Flair defend the WWF Championship. The company even went so far as to print promotional material for what would have been a generation definfing headliner, but it never went through. Rick instead defended against Randy Savage while Hulk may have ended with an infamous disqualification win against Sid Justice. Now, numerous theories have been offered as to why exactly Vince McMahon pulled the plug on such a titanic meeting. The leading presumption being that neither man was willing to put the other over. >> And I figured that's the politics. I I that's you don't even if you know anything about wrestling, you could kind of tell there's there's a probably a very easy reason why this didn't happen. Both of these guys egos was not going to let the other one go over. That doesn't work for me, brother. And Ric Flair, woo, that's not working for me. Like you already know two of these guys, their egos. No, Ric Flair was not about to lay down for Hulk Hogan. You know, Hulk Hogan was not about to lay down for Ric Flair, bro. >> Additionally, a spat of house show matches between the pair reportedly didn't live up to the dreamy expectations. Fle alluded to both theories during the interview with Ariel Helwani in 2025, saying, "I don't know the answer to that. Why the match didn't happen at WrestleMania 8. I'll tell you what I think. I don't think Hulk wanted to leave on a losing note." Which I totally understand because who am I after what he's done for the company? And number two, I don't know. Maybe they thought it wouldn't draw like it should. I have no idea. The one thing I know for sure is that it never got over in New York. Now, accounting for televised outings, Hogan and Flair contested 13 singles matches together, the best of which came upon the former's debut in WCW that proved to be a money maker for the company, grossing an estimated $5.6 million at the box office. It's fair to say that Vince really left money on the table. >> Number five, The Nexus. But no matter how hard WWE tries to find its answer to the overdone and clichéed invading outsiders trope, they'll never be able to replicate the success that WCW found with the nWo. But they could have had something close had they nailed a follow up to the next looming arrival. Interrupting a RAW main event between John Cena and CM Punk. The rookies dismantled everyone and everything in their path, eventually into the area looking like it had been struck by a tornado. John Cena took the brunt of the assault done to set him up as WWE savior and all it led to was a sevenon- showdown at SummerSlam, pitting Cena's group of staunch WWE defenders against Wade Barrett's army of NXT outcasts. It should have been the nexus match to win considering WWE was trying to establish them as this new dominant force. But given that this was at the peak of the Cena wins lol meme, WWE's most loyal protector had other ideas. Yeah, >> he annihilated Barrett and Justin Gabriel in the closing stretch of the match, eliminating Justin like he was nothing and almost immediately after that, forcing Wade to submit despite having just been struck with a DDT on the concrete floor. The Nexus had its legs cut off faster than they've been developed to the writer room. By the ends year, they were practically a non-factor on WWE programming. Number four, Randy Savage versus Shawn Michaels. And although Randy Savage was nearing his 40th birthday by the time the WWF rolled into the New Generation era, he was still a highly gifted performer. Disastrously, Vince McMahon disagreed and based solely on Ry's age, he logged the Macho Man behind the announce booth, reserving his inring duties for certain inconsequential occasions. One such occasion was not going to be against Shaw Michaels. Savage and Michaels wrestled a few times together, but Vince McMahon and his squad of creatively inept writers saw no money in a prolonged storyline between the duo. And reportedly positioned an already developed 2-year saga against the Heartbreak Kid. But with the WWF focusing on younger, fresher faces, Randy was sent packing back to the announce desk. Ry's brother, Lonnie Palfo, details Savage request to McMahon on his Genius Cast podcast, noting how keen Randy was to pass the torch. He's relegated to being the announcer and he's getting bored and he's noticing that Shawn Michaels is emerging as not just a tag team wrestler but the greatest talent in the business at the time. He calls me up at 2 in the morning and he says, "Can you find some breakaway champagne bottles?" His plan was to drink to Shawn Michael's career, pour him a glass, they would drink, they would toast, and then Randy would smash the bottle over Shawn Michaels head, >> starting a 2-year feud like the Hatfields and the McCoys, ending in Wrestlemania where Shawn Michaels loses his hair if he loses and Randy retires to the announcing table if he loses. And then they would have the greatest match ever in the history of wrestling and Randy retires. So, what happens? Pat says, "Well, Randy, we're having a youth movement, and the best thing you can do is stay in the microphone." >> Damn. >> And that's when he went to the WCW. >> Wow. >> The lack of opportunities in the ring eventually led Randy Savage to call time on his WWF career as he followed Hulk Hogan to WCW in 95 where he found immense success even at the ripe age of over 40. >> And that's the thing, it wasn't like he couldn't go. He wasn't like, it wasn't like he wasn't a personality. people know who Randy is. And the fact that, you know, back then they was just like, "Nah, bro. You too old. Sit your ass on commentary after all he's done for the company." That's kind of crazy. I mean, that would have been a very interesting story. I don't know if it would have worked out as long, you know, as for a two-year stint, but that could have been interesting if they would have did it, you know, would have took him up on his offer. But they basically said, "You old. Stick the commentary." And he said, "You know what? I'm out of here." which honestly can't get mad at that. >> Number three, Chad Gable as Kurt Angle's son. Kurt Angle, the then general manager of Raw, had a big dirty secret hidden deep inside his closet in the summer of 2017 that for some reason Cory Graves was threatening to make public. As it turned out, the Olympian had a son among the WWE locker room, a son who happened to comprise one half of the American Alpha tag team, and his name was Jason Jordan. The reveal that it was Jason who carried Angle's blood rather than the also Olympian Chad Gable went down about as well as you could imagine. And Jason did all right in the role which earned him a reign with the Raw Tag Team Championships alongside Seth Rollins. But he wasn't convincing as a supposed offspring of Kurt Angle and Chad Gable meanwhile would have been the second coming of Angle. He'd already wrestled the exact style anyway. Why did cast his eye still down with a serious neck injury just months into his family life spilling onto WWE television. An injury that ultimately cost him his inring career before any sniff of a payoff to the strain saga could be crafted in the writer room. Number two, Sting and the Abyss versus the Undertaker. Starting with his defeat of Superfly Jimmy Snook at Wrestlemania 7, the Undertaker Street became a major selling point for the Showcase of the Immortals and typically produced the hottest bouts of the night. Regrettably, however, neither Sting nor Abyss even stood across from the Undertaker on the grandest stage, despite the opportunity for both matches to become a reality. In the case of the latter, WWE reportedly offered Abyss a debut in the 2007 Royal Rumble match to set up a dreamy showdown with the Phenom at Wrestlemania 23. But the monster refused, later detailing various interviews the difficulties he encountered in leaving TNA behind. But as for Sting, not even the Undertaker is certain why Vince McMahon failed to pull the trigger. He labeled it as the biggest miss of his legendary Wrestlemania. >> That is legitimately the biggest miss ever. They had it. They legitimately had it, bro. They had it. And they didn't do it. They didn't do it. They had it. Even they could have did it when he came in around W, you know, that first go around. I know his first wrestle, first and only Wrestlemania was against Triple H. And you know how that went. They could have did it then or they could have did it after that. I know he ended up getting hurt or whatnot, so that kind of changed things, but even then, they still could have did something. Oh my god. That literally probably would have been one of the biggest Wrestlemania matches ever and it would have sold. Whatever Wrestlemania you put that on, people are going to see just for that match. That's the main event. Undertaker versus Sting Wrestlemania. The promos, the buildup leading to it. Icons going at it. Finally, the question that everyone's been asking for how many years. Who would win between Undertaker and Sting? And they didn't do it >> runner during an episode of a 6 F feet under podcast. Obviously, the people had already been clamoring for that match for a long time. It seems like a no-brainer. Why on earth would you not do that? But for whatever reason, Vince did not see it, didn't like it, didn't want it. I was like, man, this is a home run. This is an easy main event for a pay-per-view, but I really don't have an answer. I never really had an in-depth conversation with Vince about why he didn't want to do it. I think Sting, that's probably got to be the biggest miss of a Wrestlemania. Those two characters that would have done some incredible business. And while Sting finally arrived in WWE in time for Wrestlemania 31, he collided with Triple H of all people, leaving Taker to contest a good, if not forgettable, match against Bray Wyatt. And number one, John Cena's heel turn. After over two decades of fans clamoring it for it to happen, John Cena finally turned heel at the 2025 Elimination Chamber PL and it wasn't great. Pulled off specifically to say that he'd done what Vince McMahon never would. Triple H had no clear vision of what a heel cena would look like, resulting in a critically panned 4-month run. Indeed, Vince McMahon infamously held off on ever turning his biggest star player of the modern era to the dark side, but he almost pulled the trigger in 2012. With Cena slated to tangle with the Rock at Wrestlemania 28, McMahon theorized on a potential term for Cena before he nipped it in the bud. Despite that, Jon was on board with the idea and he had already began planning his new phase of his career. As he detailed to Chris Van Fleet, I heard rumblings of we're going to do it and in 48 hours and a new track, a new studio mix theme song, Final Mix, I had seven new singlets, low cut singles with boxing type robes. I'd already had the boots in storage, so I dusted them off. I was ready to go. Ironically, The Rock would later play a major role in Cena's eventual thing about it. For some reason, Travis Scott stood shoulderto-shoulder with Cena at the chamber before magically disappearing with The Rock not making a single subsequent appearance throughout Cena's run. Thanks, Rocky. But there you have it, folks. One of the biggest >> when you really think about it, he could have he was involved in potentially him turning heel many years ago only for him to be involved in him turning ill many years later and it still didn't work. Uh definitely a missed opportunity. Vince was always afraid to do it and I think I can understand why. I just think especially when you get to that legendary status as a professional wrestler, fans are not going to boo you, bro. It doesn't matter what you do. It don't. We see it with Brandy Orton. We see it with John Cena. We saw it with John Cena. Like when you get to that status where they know eventually you're about to hang it up, you're about to probably retire, it's, you know, it's right around the corner. They're not going to boo you. Why would they? Why would a fan want to boo that? No, they want to see you as long as they possibly can. They're going to cheer you no matter what you do. Now, back then, it would have made more sense to potentially turn a heel to really, you know, tap into that, but that's not something that they ended up doing. But nevertheless, hey, there's plenty of other missed opportunities that have happened in WWE. Comment them down below if you didn't see them in this video that I'm I'm sure y'all can come up with some other scenarios where WWE had gold. They had something and they didn't capitalize on it. But I appreciate all love. Sport wrote twok. Appreciate y'all kicking me. See you on the next one. Peace.