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Bray Wyatt was a once-in-a-lifetime WWE performer whose time was tragically cut short last August. Wyatt portrayed several memorable characters during his tenure. The first persona as the cult-like leader of The Wyatt Family put him on the map as a force in the company.
He attempted to corrupt babyfaces like John Cena and Daniel Bryan. Wyatt also introduced the world to The Fiend and later a stripped-down version of himself, which was the final character of his career.
While his career was memorable for its unparalleled creativity, the in-ring portion of it was marred by some questionable losses. Wyatt was born on May 23, so let's look back on five matches he deserved to win that WWE booked him to lose.
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#5. Bray Wyatt fell to John Cena at WrestleMania 30
The biggest hero for any heel to target was John Cena. The Cenation Leader was always the good guy who did things the right way. He also championed never giving up and always trying the hardest.
Bray Wyatt was the antithesis of this rhetoric, and he challenged Cena to turn to the dark side. It was one of his biggest feuds to date, and like most others, Wyatt ended up on the losing side.
Beating Cena would have put Wyatt on the map as a major star, but like many others, he fell at the feet of The Face that Runs the Place. Wyatt got a small measure of revenge by beating Cena in the Firefly Fun House match at WrestleMania 36.
#4. Battling The Undertaker at WrestleMania 31
Fans got a dream match at WrestleMania 31 between two of the best gimmicks in WWE history. Bray Wyatt challenged The Undertaker in a match between The Deadman and The New Face of Fear.
While The Undertaker was heading toward the end of his career, Wyatt was starting as a fixture on programming. Despite his best efforts and help from The Wyatt Family, The Phenom bested Bray Wyatt.
The strange part was that Brock Lesnar broke Undertaker's undefeated streak the year before at WrestleMania 30. Had that honor been saved for Wyatt, he would have instantly been a huge star. The Beast was already a made-man in WWE.
#3. The Eater of Worlds battles The Viper at WrestleMania 33
Randy Orton was in the middle of an angle where he joined The Wyatt Family. He joined up with Wyatt and eventually won the 2017 Royal Rumble.
The Viper declined to challenge then-WWE Champion Bray Wyatt as he had won the title at Elimination Chamber the month before The Show of Shows. Despite the initial claim, Orton eventually challenged and defeated Wyatt to win the title.
Winning the title was exciting for Wyatt, but he was only given a month-long reign to build a WrestleMania program. The Eater of Worlds deserved better and could have established himself with a meaningful run.
#2. Goldberg crushes The Fiend
Things were finally looking up for The Fiend after he defeated Seth Rollins for the Universal Championship at the 2019 Crown Jewel event. The title changed hands during the infamous red light Hell in a Cell match.
It was exciting for Wyatt to get another shot with a major title, but the ending was anything but exciting. WWE wanted a Goldberg vs. Roman Reigns match for WrestleMania. Bookers then had The Fiend fall to the aging Legend at Super Showdown just six weeks before The Show of Shows.
It essentially took the air out of the work Bray Wyatt had done to craft The Fiend and win the title. Goldberg would then drop the title to Braun Strowman at WrestleMania as Roman Reigns stayed away from crowds due to COVID.
#1. Another short title run ended
Officials wanted Reigns to beat Goldberg for the title at WrestleMania, so whoever was Champion when The Big Dog returned was going to lose. Reigns re-emerged in WWE at the end of SummerSlam after Wyatt regained the title from Strowman. His return overshadowed the big win.
The Big Dog was on a mission to claim the Universal Championship, and he did so the next weekend at the Payback event. Bray Wyatt only held the title for a week before dropping it to Reigns.
It was another slight to Wyatt to prop up a star who didn't need the title. The quick title swap kicked off Reigns' 1,300-day run that ended in April.
