#2 Buff Bagwell (3-month WWE run)
Buff Bagwell took part in one of the most infamous matches in WWE RAW history when he challenged Booker T for the WCW World Heavyweight Championship in July 2001.
At the time, WWE wanted to make WCW its own brand within the company. This meant that the main event of RAW had a WCW theme, including different ring skirts and announcers.
Unfortunately for Bagwell and Booker T, WWE’s loyal fans decided to hijack the match with “boring” chants before Steve Austin and Kurt Angle attacked both men to cause a disqualification.
The disastrous match, coupled with complaints about Bagwell’s backstage behavior, led to WWE releasing the five-time WCW Tag Team Champion just three months after taking over his WCW contract.
Like Cain Velasquez, Bagwell’s only televised WWE match came in a World Championship encounter, but neither Superstar likely expected their time in the company to come to an end so quickly.
WWE’s website even published an article in 2013 describing Booker T vs. Buff Bagwell as “the most awkward match ever”, but Bagwell declined to comment when he was contacted by the company for the article.