6 times Bray Wyatt lost when he should have won
In the world of WWE, it can be very difficult for a new, young Superstar to get a foothold. A couple of recent call-ups from NXT have fared better than expected (such as Ricochet, for example, and after a brief period of struggle, Andrade). But it's tough to break-in to WWE these days unless you're already a star coming from somewhere else (unless your names are Luke Gallows and Karl Anderson).
One very specific, and somewhat peculiar case, is Bray Wyatt. The character portrayed by the third generation wrestler Windham Rotunda was one that excited many people when it came to light in NXT in 2012.
The Wyatt Family, after weeks of vignettes warning of their arrival, appeared on RAW in the summer of 2013 to attack Kane. This made sense. You go after the biggest guy in the yard. Kane's a dependable veteran who has given himself up many times to make younger, newer talent look good. That is exactly what Kane did, and it immediately propelled Wyatt (along with Harper and Rowan) to stardom.
Wyatt stayed strong throughout the rest of 2013, which saw him and his Family mostly dominate a feud against CM Punk and Daniel Bryan, both big Superstars and multiple time World Champions. Wyatt even got a singles victory over Bryan at the Royal Rumble in 2014.
That was a very significant victory for Wyatt. It marked the conclusion of his second big storyline, both of which he came out as the winner. In the second, he was able to defeat the man who would win the main event of WrestleMania less than three months later.
Things were looking very good for Wyatt. He was on top of the world (or, actually, he had it in his hands) and he looked unbeatable. But he didn't stay undefeated for long. The Firefly Fun House and The Fiend have reinvigorated Bray Wyatt after a number of disappointing years, but there's a reason those years were disappointing.
#6 Randy Orton (WrestleMania 33, 2017)
Bray Wyatt had been having a rough go of it. After a strong, dominant start, the leader of the Wyatt Family suffered a number of crippling defeats. There were victories that peppered his timeline, but they were few and far-between, and he was never able to follow up and string together a set of big wins and stayed stagnant. To sum up a long story with a short, cliched sentence: Wyatt was all talk, no action.
It seemed like things were going to turn around for Wyatt in the latter half of 2016. He confronted Randy Orton and got the better of the veteran Superstar at almost every turn. It came to the point where Orton seemed to take the phrase "if you can't beat 'em, join'em" to heart, and joined Wyatt and Luke Harper to create a new Wyatt Family. The team would have great success for the rest of the year and into 2017. They were together for around four months. Along with Harper they became SmackDown Tag Team Champions (defending it like The New Day, with the Freebird Rule) but lost the titles after only a few weeks. It was the Harper and Orton team which lost the belts, causing Wyatt to attack Harper and oust him from the Family.
As it turned out, this was all part of Orton's plan to weaken Wyatt. He struck with the Wayyt Family leader for a little bit longer, as the men teamed up in the Royal Rumble match, making it to the final three men. Roman Reigns eliminated Wyatt (Randy could have helped, but didn't) and was very shortly eliminated by Orton, who would claim a WrestleMania title shot.
Bray Wyatt finally won the WWE Championship, to the joy of his fans, in the Elimination Chamber match the following month, and Orton, as the No. 1 contender, pledged that out of respect and reverence for The Eater Of Worlds, he would not challenge him for the title at WrestleMania (he could have challenged Goldberg instead, but that would have been a bad idea).
In the end, Orton would burn down the cabin where Wyatt spent much of his life, and the location in which Sister Abigail was supposedly buried. He revealed that joining the Wyatt Family was a ruse from the beginning, and being able to take the WWE Title from Wyatt at WrestleMania would just be icing on the cake.
With the fans almost split down the middle in terms of supporting the Champion and Challenger, Bray Wyatt would go on to lose his championship after only 49 days. This would mark the final big loss of his career to that point, and possibly his biggest one of them all. He also never received a rematch for the championship.