2018: Dean Ambrose's Heel Turn
When Dean Ambrose returned to come to the aid of Seth Rollins in the summer of 2018, it was a matter of when (not if) he would turn heel on his Shield brother. It was like a ticking timebomb. After another Shield reunion, Roman Reigns gave the WWE Universe some sad news by announcing that his leukemia had returned. To pile on the emotions on that very night, Ambrose turned heel on his best friend and considering the highly emotional circumstances, it was one hell of a turn.
On the night when their brother announced he had to step away from the ring, the two of them captured the RAW Tag Team Titles and then in front of an emotionally spent crowd, Dean Ambrose executed the most heartless character change in a very long time. It was perfect. Unfortunately, everything that followed was far from perfect. Ambrose did not give a proper explanation for attacking Rollins, despite it being so easy to write.
Vince McMahon insisted on him doing the vaccination skits and name-dropping Roman Reigns in a vile manner. There were several outrageous ideas that were likely classed by the chairman as "such good s***." The storyline with Seth Rollins ended up flopping so badly when it was the easiest thing to get right in a whirlwind time on the Red Brand. Even their matches failed to click. This eventually led to Dean Ambrose leaving the company in April.
The alignments were seemingly perfect and the story was so easy to tell, but WWE utterly botched one of the most exciting heel turns of the decade. Bizarrely, Daniel Bryan turned into a villain a few weeks later and it was perfectly executed. This was such a wasted opportunity at a time when WWE needed some good programming more than ever.