12. Worst: Jim Duggan (1988)
It saddens me to place the very first Royal Rumble winner, “Hacksaw” Jim Duggan, on our list of bad Rumble winners. Duggan won the inaugural battle royal in 1988, but it was very different from the Rumble spectacular that we know today. The simple fact is that the event was an experiment for WWE (WWF at the time) and they simply had no idea where it was going to go. While this is an interesting bit of history to go with the Rumble, these facts showed with their selection of Duggan as the winner. Though often a fan favorite, he certainly was not a top star in the company. Should WWE have chosen someone more prominent to win the first Rumble, it would have received much faster recognition. As it stood with Duggan as the winner, it would be quite a few years before the Rumble would begin to amount the acclaim that it receives today.
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