10 Worst WWE Royal Rumble Winners Ever

6. Mr. McMahon (1999)

Vince McMahon worst
WWE

Vince McMahon is an evil, malevolent human being. That statement has no relevance to this list entry, but it wouldn’t get stated enough if it was stated twice a day. 

The Mr. McMahon character had no business winning the Royal Rumble. Except he did, in 1999. 

He was a stunt winner fitting for the time. It was a time not for prestige or climbing mountains to succeed, but for great whopping breasts and stupid plot twists that were retconned within weeks. 

While the result “made sense” within the warped context of its era, it was still rubbish. Mr. McMahon winning the Rumble match only exposed that the roster depth was shocking and you’d have to endure yet another retread of the Steve Austin Vs. Undertaker feud within months. And, sure enough, you did. Even the Undertaker knew it sucked which is why he took on the American Badass persona a year later. 

The experiment was cute, but unlike the extraordinary Over The Edge 1998, the wild, OTT TV-style booking did not translate well to PPV. 

McMahon missing the entire match only to win at the end was telegraphed, and an hour of 1999 undercard acts carrying a pointless Rumble was as abysmal as you’d expect.

Contributor
Contributor

Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!