#2 Braun Strowman wins Money in the Bank and turns heel at the peak of his popularity
Another few mistakes WWE made with Braun Strowman came during the summer of 2018. This was him on his last legs as a possible babyface megastar. He won the Money in the Bank Ladder Match, despite not needing the briefcase at all.
Strowman could have easily just gotten a Universal Championship match at will, having won the 50-man Greatest Royal Rumble Match in Saudi Arabia a couple of months earlier. It should have counted for something. The Monster Among Men was already over as well, as other superstars could have done with the boost.
But what made the decision even worse was the fact that Braun Strowman did not even successfully cash in his Money in the Bank contract. He failed to become the Universal Champion, following an ill-advised heel turn.
Strowman became a villain after The Shield had reunited to stop him from cashing in on Roman Reigns, aligning himself with Drew McIntyre and Dolph Ziggler to counter the star-studded trio. He cashed in ahead of time, setting up a Hell in a Cell Match between him and Reigns for the Universal Championship.
It ended in the worst possible way, a No Contest. Brock Lesnar returned, invaded the cell, and attacked both superstars to the point where the referee called the match off. From his heel turn to a terrible Money in the Bank cash-in, Braun Strowman's stock plummeted during this period. He would never be the same.