Most Convoluted Storyline - Build to Triple Threat Main Event of WrestleMania 35
The build to the main event of this year's Show of Shows started at SummerSlam 2018. Becky Lynch had earned a title shot at the show, but Charlotte Flair was given a chance right away after being away for a few months. Instead of winning a series of matches like Lynch, she won one bout.
After Flair won, it kicked off the anti-hero Lynch storyline. WWE wanted the fans to cheer Flair, but after already having so many reigns, the fans cheered for who they wanted to. Because of that, Lynch eventually won the title back and was slated to face Ronda Rousey at Survivor Series. She got hurt, however, and the match was postponed.
Once Lynch returned, she lost the title, won the Women's Royal Rumble and intended to challenge Rousey. But in between earning the right and actually getting to capitalize on it, WWE threw a lot of darts at a non-existent dart board. Lynch was suspended but reinstated for not trusting the McMahons.
She was then stripped of her title shot, and instead of earning it, Mr. McMahon simply put Flair in the match instead. Lynch had to re-earn her title shot by beating Flair at Fastlane, but The Man only won because Rousey interfered. Gotta keep Flair looking strong.
Even though she re-earned her shot at 'Mania, the ladies were still going to main event the show.
Two weeks before the Show of Shows, McMahon didn't think that the stakes were big enough so he had Flair randomly challenge and defeat Asuka for the SmackDown Women's title. It made the match Winner Takes All, but when all was said and done, Lynch won both titles.
The result was fine but the direction they took to get to the end point was too confusing. It killed Asuka's credibility and gave Flair another meaningless reign en route to breaking her father's record.
Had WWE just stuck with the initial plan of Rousey vs. Lynch then it would have been fine, but they overthought practically every unneeded detail.