In the way that it is now, the WWE has been around for around five decades, and in that time we’ve had many epic eras, many larger-than-life competitors, and at the end of the day as it’s a wrestling company that has had many fantastic, thrilling wrestling matches. Yet the be all and end all of wrestling is its top Championship, and WWE’s has had a very storied tenure. The WWE Championship has seen 50 men claim it as their own throughout those five decades, starting from Buddy Rogers in 1963 all the way to current Champion Jinder Mahal, and while the belt has mainly kept its prestige over that time, with guys like Hulk Hogan, Steve Austin, Shawn Michaels, The Rock and AJ Styles proving it’s one of the most important in the business, it’s also had it’s fair share of terrible holders.
However, that’s not the only World Title the WWE has ever had, as it promoted the World Heavyweight Championship following the purchase of WCW, as well as the current RAW Championship known as the Universal title, and while those have been seen as inferior to the WWE title, they are considered world titles in the WWE nonetheless.
16 Worst To Win – Alberto Del Rio
On the independent scene in Mexico, Alberto El Patron was one of the biggest stars in the entire industry, so when he came to the WWE, it was a huge deal, but as time went on and the company followed their pattern of turning every top heel babyface, the man then known as Del Rio lost his luster, and while he was still a good wrestler, his character just wasn’t worthy of winning the WWE title. What made this even more disastrous was the timing of it, as Del Rio was chosen to cash in his Money in the Bank contract on CM Punk just a few short weeks after his historic victory at the MITB event over John Cena, and fans soon began to realize just how bad Del Rio had become. He could still work a decent match, but his character was beyond stale, and that in combination with the timing of it just lands him a spot on our list.
15 Best To Never Win – Roddy Piper
Roddy Piper began his rise to stardom in a time where the WWE didn’t have the monopoly over the wrestling industry like it mostly does today, and despite never reaching the mountain top in Vince McMahon’s company, he racked up a very impressive 34 championships throughout his legendary career. Still, we would have loved to have seen him on top just once in the WWE. Piper is widely regarded as the top heel in the history of the wrestling industry, and one of its greatest entertainers, and despite bringing prestige to the already prestigious Intercontinental title, the company never had the opportunity to put its biggest prize on him. At the end of the day, most people who watched wrestling during Piper's prime will remember him as one of the top stars regardless of his lack of World Championship pedigree, but you can’t help but think WWE missed a major trick by not putting Piper on top at least once.
14 Worst To Win – Goldberg
In his day, Goldberg was never a good wrestler, but WCW managed to disguise his weaknesses so well to the point where he was one of the biggest stars in the history of the industry, but like they often do, the WWE managed to stuff up a sure thing, and with his two championship reigns in the WWE, Goldberg just wasn’t the star he should have been. Don’t get me wrong, the fans still treated Goldberg like a star, but especially with his Universal title reign in 2017, fans today grew discontent with his in ring limitations, and his one-month reign with the championship became a joke. His return was electric, and his victory over Brock Lesnar was one of the most shocking and exciting moments in recent WWE memory, but once the fans saw through Goldberg, they turned on him, which shows what a mistake the WWE made by putting the Universal Championship on a 50-year-old man.
13 Best To Never Win – Rick Rude
Most of the people on this list will mainly be remembered for their time with the WWE, but Rick Rude is not one of them. Despite being a very prominent character as “Ravishing” Rick Rude for the company, he will likely be remembered by most fans for his work in Jim Crockett Promotions and WCW following his departure from Vince McMahon’s company. Rude lasted just three years in the company, but made an impact as one of their best heels, as he debuted as part of Bobby Heenan’s family, and he had memorable feuds with the likes of Paul Orndorff, Jake Roberts and The Ultimate Warrior. Despite winning the Intercontinental title, and being seen as one of the most talented performers in the entire business, Rude didn’t last long enough in the WWE to get to the mountaintop, but his efforts were enough to earn him a place in the WWE’s Hall of Fame just this year.
12 Worst To Win - Diesel/Kevin Nash
Like Razor Ramon/Scott Hall, Kevin Nash will most likely be remembered by wrestling fans for his time with the nWo in WCW, but what he and the WWE would likely want you to forget is just how poor he was during his WWE title run with the company in the mid-90s. Despite feuding with the likes of Shawn Michaels, Bret Hart and The Undertaker, he still struggled to have a decent match with any of them. It’s been pointed out that he was one of the lowest drawing champions in the history of the company, and while that can’t be all put on him, as the overall booking at the time was shockingly bad, it is telling of how bad a wrestler he was inside the ring. Whether justified or not, he will always be considered one of the worst WWE Champions out of the 50 the company has so far crowned.
11 Best To Never Win – Shelton Benjamin
It’s unlikely when clicking on an article like this that you would have expected a perennial mid-carder like Shelton Benjamin to appear, but when you think about the career he had with the WWE, he certainly deserved a main event push as he was one of the most talented, athletic and complete wrestlers the WWE have ever had. There were many chances to pull the trigger on Benjamin too, as he was one of the hottest stars in the company around WrestleMania 20-21, but despite starring in every Money in the Bank Ladder match, Triple H, John Cena, Shawn Michaels and others just always clogged up the main event scene. It's just been reported that Benjamin will be back to the company that made him a star, and it’s unlikely he will climb that mountain now that he's 42, but he still should be remembered as one of the most underrated stars in the company's history.
10 Worst To Win – Sid
Despite being one of the most limited and botch prone (particularly on the microphone) superstars in wrestling history, Sid Vicious or Sycho Sid had one of the more impressive careers of anyone on this list. Despite that, he will always be one of the worst performers to win a World Championship, in the WWE or any other promotion. Somehow despite his poor in-ring abilities, Sid managed to headline not only Starrcade, but WrestleMania as well, on top of being a six-time World Champion, two of those coming during his tenure with the WWE. It’s easy to see what Vince McMahon loved in him, especially at this time, but despite his look and solid charisma, he just wasn’t as good as so many other top performers in the business, but all credit to him, he managed to have a very successful career that spanned the '80’s, '90s and early-2000s.
9 Best To Never Win – Vader
Big Van Vader is one of the most divisive performers in wrestling history, as he was considered a super heavyweight that could do things more suited for the cruiserweights of the industry. Despite having a career that spanned from 1985 to the past few years as a semi-retired performer, he never managed to win the big one in Vince McMahon’s company. During his long, illustrious career, Vader wrestled for all the top promotions in the world, from All Japan Pro Wrestling, New Japan Pro Wrestling, WCW, Pro Wrestling NOAH, WWF and even TNA, and while winning the World Title in several other promotions, he was never in the WWE long enough for that to come to fruition. During his three years with the company, he improved his stock in the wrestling world and became a worldwide star, and while fans will still see him as a great performer and one of the most innovative of all time, it’s unfortunate that he never had such a signature moment.
8 Worst To Win – Jinder Mahal
While we truly hate to pile on to the Jinder Mahal hate, as he has done an adequate job of improving in his time with the WWE Championship, he just isn’t main event material, as his character is lacking in originality, and he is incredibly limited and boring in the ring. The WWE put Jinder on top solely to try and cash in on the Indian market, and while he’s performed much better than anyone expected him to, he had been nothing but enhancement talent for the WWE for quite some time, and that’s not who should be in the main event. Maybe with more time, Mahal will fit in as a main eventer, but for now, he’s still not a very good performer holding on to the WWE title, and someone like AJ Styles needs to come along and dethrone the Maharaja.
7 Best To Never Win – Mr. Perfect
Like his name would suggest, “Mr. Perfect” played by Curt Hennig was one of the best professional wrestlers of all time, and while he did win the arguably more prestigious (at least at that time anyway) Intercontinental title, the WWE never pushed him to their main event scene, which is a shame as he truly deserved such an honor. Throughout his 23-year career in the business, Henning crafted a legacy which will live on forever, as he was one of the most technically gifted performers in the business, but during his three runs with WWE that lasted a cumulative 10 years, he never cracked the main event scene. Like others on this list, Perfect was inducted into the WWE Hall of Fame in 2007, and will be remembered as one of the greats despite this, but it would have been a much deserved accolade had he of achieved it.
6 Worst To Win – Jack Swagger
As a performer inside the ring, Jack Swagger was adequate, and he even had some pretty good matches throughout his WWE tenure, but with the limited charisma, character and mic skills, it’s very surprising that the WWE put their World Heavyweight Championship on him. Just a short while after he won Money in the Bank at WrestleMania XXVI, that’s exactly what they did. His reign didn’t last long, because it became clear that the WWE made a huge mistake putting their second-biggest title on him, and while he would go on to some mid-card success during the rest of his WWE tenure, he would understandably never again rise to those heights. At the end of the day, the WWE probably could have done more to make Swagger look like a genuine threat, but after all the chances he was given, he just wasn’t an adequate champion in the WWE.
5 Best To Never Win – Jake Roberts
Jake “The Snake” Roberts is one of the most well-known wrestlers of all time, and while that’s not always been a good thing, as he has struggled with life following his retirement from the wrestling business, he will always be remembered by those inside the industry as one of the best to ever step inside a ring, but that wasn’t his strong suit, as he is regarded as one of the best talkers in WWE history. Sure, he didn’t have levels of charisma like The Rock, but he was very cerebral and had a dark charisma, and used psychology better than any other in wrestling history, but somehow the WWE didn’t feel him worthy to hold their top prize. This is very surprising as he was one of the most over stars in the company for his entire tenure, but thankfully, his character and in ring performances will transcend any accolades that he didn’t manage to achieve.
4 Worst To Win – The Great Khali
If Jinder Mahal is bad, and he is, that’s nothing in comparison to his fellow countryman The Great Khali, who somehow became World Heavyweight Champion despite barely being able to work an exciting match or program with anyone. But it just proves how dedicated Vince McMahon is to pushing those guys who fit his criteria. When he debuted out of nowhere to destroy the legendary Undertaker, fans were shocked and interested in his character, but when they realized how limited he was all around, they just stopped caring. Despite this, the WWE put their second top prize on him, and while some may have seen him as a legitimate champion, looking back on it, he was nothing but a wasted experiment from the WWE.
3 Best To Never Win – Razor Ramon
When looking back on the wrestling business in the '90s, there are a few names that stand out as more important than others, and one of those very key players was Scott Hall, who portrayed Razor Ramon in WWE, and despite having major success in every single company that he worked for, he never managed to win the big one during his WWE tenure, and that’s a major shame. If he had of stayed with the WWE instead of making the huge leap to WCW with nWo stablemate Kevin Nash, maybe we would be telling a different story about Hall, who, unlike Nash, was a fantastic all around performer. At the end of the day, few wrestlers in the 1990s experienced the success that Ramon/Hall did, but we only wish a little bit more of that could have come with the WWE.
2 Worst To Win – Vince McMahon
Whether you like him or you hate him, and it seems as he gets older a lot more people begin to hate him, you can’t deny that Vince McMahon is an icon in the wrestling business, as he built the WWE into what it is today. While the character Mr. McMahon was one of the most over villains as he opposed Stone Cold Steve Austin in the late '90s, it doesn’t mean he was ever going to be a good World Champion, yet he somehow won world titles… twice. McMahon won the WWE’s top prize during the Attitude Era, and a decade later captured the ECW World Heavyweight Championship, and while it may have helped business, as the character was the most hated man in the business, it definitely didn’t help the credibility of either title.
1 Best To Never Win – Owen Hart
Obviously we all know the reason why this one didn’t happen, as Owen Hart tragically passed when an accident occurred live on WWE PPV, and whether you liked him or not, it was one of the biggest tragedies in wrestling history. If this never had happened, you have to assume that Owen would have won the big one sooner or later, even if he had to follow brother Bret to WCW to achieve it. But his immense talent was obvious, and there were many chances for the company to put the big belt on him before that tragic, fateful day. Through no fault of his own, Owen will always be seen as one of the biggest “what ifs?” in pro wrestling history, and despite never winning the WWE title, he will be remembered as one of the greatest to ever step foot inside a wrestling ring.