#1 Booker T
Booker T was pushing super-stardom in early-2003 and a win over the biggest heel in the WWE at Wrestlemania 19 seemed perfect for the star. Booker had enjoyable programs with Steve Austin, The Rock and a host of other superstars from 2001 to 2003 and it was finally time to pull the trigger on the final WCW World Heavyweight Champion.
The build-up to Wrestlemania 19 was not comfortable viewing, as Triple H made racial slurs towards Booker, stating that 'people like him' don't win such matches. His character was verbally being assassinated by Triple H, and all that Booker needed to do for redemption was deliver comeuppance to the arrogant heel that was Triple H.
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It was the only logical conclusion, as Wrestlemania is where storylines culminate with heartfelt crowd responses. However, Booker T lost to Triple H clean after a pedigree which saw HHH take his sweet time before pinning Booker, making him look weak. This still stands as one of the worst decisions in company history and one of the worst examples of backstage politicking by Triple H or anyone else ever.