231988: Jim Duggan
The trivia answer regarding the first winner of the Royal Rumble match will always be Hacksaw Jim Duggan. Pat Patterson pitched the idea of the Rumble, delivering the first PPV in 1988 with a twenty man battle royal before the WWE upgraded it to thirty competitors. Duggan won the first
ever Rumble to always have the accomplishment associated with his name. The WWE Championship eluded him as the first Rumble didn't come with a title shot, but the Rumble win is almost as noteworthy in wrestling history.
Duggan would have a legendary career with runs in WWE and WCW. Wrestling fans adored Duggan for his fun-loving personality. The 63 year old is still going, wrestling matches on independent shows across the country. Duggan obviously is limited by the aging process but still loves performing in front of crowds that appreciate his past work.