#6. The Chairman has also won a Royal Rumble
The 1999 Royal Rumble had a weird result, to say the least. Having realized the potential and popularity of the Attitude Era and Mr. McMahon's involvement, WWE went completely crazy to give fans what they wanted, and also what they didn't.
First, McMahon forced Steve Austin to enter the event at #1. Then, the Chairman decided to enter at #30 himself. However, commissioner Shawn Michaels overruled his decision and forced him to enter at #2.
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In his first and only appearance at the eponymous battle royal, Mr. McMahon did the unthinkable by winning the event by last eliminating The Texas Rattlesnake with the help of a distraction from The Great One.
#5. Lex Luger shared his victory which he achieved at his debut Rumble
Before AEW, ROH, or IMPACT Wrestling, WCW was a legit threat to WWE (then WWF). Hulk Hogan, the top star of Vince McMahon's promotion, left the company to join its rival in 1993.
The producers of WWF saw Lex Luger as the next big thing. They attempted to push him to the main event and make him the biggest star in wrestling. His achievements include a Royal Rumble victory, which he shares with Bret Hart. This is the only instance of co-winners in the Rumble.