#1.) Defeating The Undertaker at WrestleMania 33
This one has to be the most bittersweet moment in Roman Reigns’ career. He would become only the second man to defeat The Undertaker at WrestleMania, seemingly retiring him for good. It seemed like it was the end of The Phenom‘s career, but he did end up returning for a 3-minute match the following year at WrestleMania 34 to squash John Cena.
Growing up in the wrestling business, Undertaker was likely held in the highest regard and having to put down his idol must have been both an honor and bitter moment for The Big Dog. It could be seen in his facial expressions as he never once smiled after winning. A backstage photo after the match saw Roman Reigns sitting alone and looking down in disappointment. One can only wonder what went through his head after the biggest moment of his career.
