To date, there have been 29 televised Royal Rumble matches, and yet, despite its billing as the second most important match of the year (behind WrestleMania's main-event), the history of the match is uneven. Arguably, 15 of the 30 winners were the wrong guy at the wrong time. Even when looking at the other 15, you're left with about eight who are in the "take em or leave em" category. Which means only eight out of 30 winners can be pointed to as "the right guy at the right time." That's a pretty poor track record.
The eight perfect winners, in this writer's opinion, were Ric Flair in 1992 (when he won the WWE Championship), Bret Hart in 1994 (when Vince finally started to get behind him as the face of the company), Shawn Michaels in 1996 (the beginning of the great "boyhood dream" storyline), Steve Austin in 1998 (which officially cemented him as the top superstar in the company), The Rock in 2000 (the hottest performer during the hottest period), Austin again in 2001 (en route to the biggest main-event ever), Chris Benoit in 2004 (en route to the storybook ending at the end of WrestleMania XX), and Batista in 2005 (which cemented him as the other top superstar of his generation).
Other than those eight, the Rumble's history is of producing "meh" winners (who served a purpose but didn't set the world on fire) or outright bad ones. Let's skip the "meh" (Studd in 89, Hogan in 91, Yokozuna in 93, Michaels in 95, McMahon in 99, Undertaker in 07, Cena in 08, Edge in 10) and go straight to the bad.
Here are the 15 worst Royal Rumble winners, in order from bad decisions to ABSOLUTE WORST DECISIONS, followed by who obviously should have won that year...
15 1988 - JIM DUGGAN
Jim Duggan won the inaugural Royal Rumble, as a USA Network Special Event. Though he’s kind of a joke today, Duggan was a popular mid-tier superstar back then, comparable to Dolph Ziggler in terms of popularity and stature. But can you imagine Dolph Ziggler winning a big marquee match that was the first of its kind? And yet, Duggan will go down in history as the first televised winner of the Royal Rumble (One Man Gang won an untelevised trial run a few months prior).
So who should have won? Why, the Ultimate Warrior of course! He was right at the beginning of a push that would see him win the IC title at SummerSlam that year. The first Rumble was low on starpower and Ultimate Warrior was already getting hot with fans. A win to start 1988 would been a big boost to the new superstar.
14 1997 - STEVE AUSTIN
No one’s going to argue that Stone Cold is not one of the greatest Rumblers of all time. He’s the only three time winner after all, but that first win has an asterisk next to it. He won by eliminating arch-nemesis Bret Hart, but was later disqualified when it was revealed that he’d previously been eliminated (and reentered the match without refs noticing). As a result, a very popular young superstar (though a heel) had his big break yanked from him, and from fans who were hungry to see a fresh face in the main-event.
Austin will go down in history as the winner of the Rumble, but he never got his chance to main-event WrestleMania 13. So who should have won? Austin. Except he should have wrestled Bret Hart for the title in a Submission Match. Don’t ask me how to get from there to there, I’m just saying that’s how it should have been done.
13 1995 - SHAWN MICHAELS
HBK’s toiled away for years in a tag team and then in the mid-card, before finally getting his big break in 1995, winning the Rumble and facing champion-Diesel. The problem was, Michaels was a heel in 1995 and it’s hard to have your first main-event run come as a heel; fans are predisposed to boo and reject your being a legit threat at the top of the card. It’s easier to be a babyface breaking in, because fans naturally root for an underdog.
The Michaels/Diesel feud failed to spark with fans and their match at the terrible WrestleMania 11 went over like a lead balloon. If the whole Road to WrestleMania could have been done over, who should have won the Rumble? Bret Hart, of course. He was the more reliable star and had a natural story in his feud with Diesel (the guy who beat the guy who stole the title from him).
12 1994 - LEX LUGER
The thing about Bret Hart is Vince never fully bought into him as the next Hulk Hogan. He always used the always-popular Hart to keep his main event warm until the next real face of the company came along. There was Diesel and HBK and eventually Austin hit the groove, but in the beginning there was Lex Luger, whom Vince tried to mold and force onto the fans as the next great superstar. But Luger (who was always a better heel) lacked the charisma or it-factor to connect with crowds. Vince persisted though and booked Luger to co-win the Rumble with Bret Hart. Even when fans clearly supported Hart, Vince still intended to put the belt on the “All American” and only changed his mind when Luger was caught breaking kayfabe days before WrestleMania X.
The better option would’ve been to give the Rumble to Bret and ride him as the top guy until Austin came along.
11 2011 - ALBERTO DEL RIO
When Del Rio won the 2011 Rumble, he’d only been in WWE for a few months. Vince saw potential in him and fast-tracked him to the main-event. Within five years he’d hold multiple titles and accolades (WWE title, World title, US title, Money in the Bank, multiple WrestleMania marquee matches) but never resonated with the crowds. Rushing him to win the Rumble was the ultimate in “too much too soon.” Fans responded to his surprise victory with a mixture of indifference and annoyance; many fans were unfamiliar with him, the rest didn’t care.
So who should have won in 2011? CM Punk. He was over and he was ready. A win there, followed by a Cena title win in February could have given us a big title match worthy of WrestleMania XXVII. The Rock could have interfered, setting up a long-feud with both of them climaxing in a triple threat at WrestleMania XXIX. Alas…
10 2003 - BROCK LESNAR
Brock Lesnar’s 2003 win might not seem like a bad idea because it was supposed to be just one in a series of achievements in a decade-long career. Instead, a year after he won, he was on the way out. Lesnar’s abrupt departure is not why his 2003 win was a bad one, however. Actually it’s the whole booking of Lesnar between November of 2002 and November of 2003. His entire run as a babyface was wrong from the start. The monster Lesnar should not have abandoned his role as a heel so quickly after debuting and he certainly should not have lost the title so quickly after winning it (and certainly CERTAINLY not to Big Show).
Instead Lesnar should have remained dominant while his WrestleMania opponent, Kurt Angle, won the 2003 Rumble. That would have given Angle the chance to be the underdog hero against the monster heel, providing a much better story all around.
9 1990 - HULK HOGAN
This Rumble takes place in that early era before the event came to be the kickoff to the road to WrestleMania, back when the match was a glorified exhibition. Hogan won the 1991 edition and that’s fine; the biggest star should have his name on the record books for the match. Hogan also won the 1990 event, however, and that’s where I draw the line.
Mr. Perfect was undefeated (on television) going into the 1990 Royal Rumble and was in the midst (alongside The Genius Lanny Poffo) of a bubbling-over feud with Hulk Hogan. Naturally the two of them would be the last two men standing at the Royal Rumble. As much as Hogan’s fans loved to see their hero eliminate Perfect, the right call should have been for him to defeat Hogan in the mostly-meaningless Rumble, setting up a big showdown between the two of them at WrestleMania VI…but I’m a shameless Hennig fan.
8 2016 - TRIPLE H
With many “bad Rumble winners” it’s more than just the winner, it’s also about the overall booking going on around it. In this case, you have the terrible Roman Reigns vs. The World storyline that everyone whose name wasn’t McMahon was tired of. Everyone could see the writing on the wall and predict a Triple H “surprise” entry, victory and title loss to Roman Reigns at WrestleMania. What’s frustrating is usually Vince likes to swerve fans when they predict what’s going to happen. Not here, though. They followed the script exactly as fans guessed it, leading to a Royal Rumble, Road to WrestleMania and main-event in Dallas that generated the least amount of enthusiasm since HBK vs Diesel.
What to do differently? Maybe Dean Ambrose? He would get his title shot that February and the fans responded tremendously to him. Maybe give the fans what they want and avoid the boos?
7 2012 - SHEAMUS
What’s frustrating is usually Vince likes to swerve fans when they predict what’s going to happen. In 2012 Chris Jericho returned with a light up jacket and a troll face and became the biggest heel on the roster. He entered the Rumble with a promise to “end the world” as we know it. Everyone and their uncle predicted the same thing: Jericho wins the Rumble, feuds with CM Punk (the so-called “Best in the World”) and has a big title match at WrestleMania.
Instead of giving fans simple, logical booking that they actually wanted, Vince threw a swerve at everyone and gave the Rumble to Sheamus, who last eliminated Chris Jericho, making the eventual WWE #1 contender look like a goober in the process. Sheamus meanwhile had an opening match fiasco with Daniel Bryan that ended up making Bryan into a superstar.
So..I guess it worked out?
6 2006 - REY MYSTERIO
Set aside that Mysterio’s win was a naked exploitation of Eddie Guerrero’s death. Forget that and it’s still bad booking. I’ve thought a lot about WrestleMania 22 and I think that one, IV and X8 are the three most wrongly-booked WrestleManias ever. John Cena should've won the Rumble that year, Edge should've defended the WWE Title at WrestleMania (like The Rock vs Austin in 1999), and the World Heavyweight Title should've been defended in a tournament between January and Mania, ending in a final four, with three matches on the card: Triple H vs. Randy Orton, Mark Henry vs. Rey Mysterio, and Rey Mysterio vs. Randy Orton. Also Kurt Angle should've taken on Undertaker.
The whole card was wrongly-booked but if they simply had a little more faith in Edge to carry the show with the still-newish John Cena, the dominos could have fallen a different way and we might have gotten a great PPV out of it.
5 2013 - JOHN CENA
Speaking of John Cena, while he had every business winning the 2006 Rumble, he had no business winning the 2013 edition. As fun as the build-up to “Once in a Lifetime” occasionally was, there were very few actively longing for Rock vs Cena II. Only Vince McMahon wanted it, because he wanted Cena to have the torch officially passed to him (nearly a decade after he became the top superstar, but I digress).
The right play should have been for The Rock to win the Royal Rumble, for Cena and Punk to feud in January and February with no decisive winner and have WrestleMania XXIX be main-evented by a triple threat, finishing the story that should have started between the three of them at WrestleMania XXVII. As for who would wrestle Undertaker in that scenario, my answer would be “Chris Jericho didn’t need to lose to Fandango that year, did he?”
4 2009 - RANDY ORTON
Granted, the feud between Orton and the McMahon family sort-of worked. WrestleMania 25 was a big anniversary year so naturally the McMahons made it all about them. Randy was the perfect slimy villain for the whole clan to feud with, and Triple H was the appropriate family champion. But on a practical level, it didn’t work. Rumbles that end with a heel victor feel wrong. That moment is supposed to be about a babyface who’s endured a grueling match and is now battle-tested to slay that dragon at WrestleMania. Instead the dragon was…a babyface champion. Wouldn’t it have made more sense for Randy to be the champion and for Triple H to win the belt and thus the family honor? And you wouldn’t need the Rumble for that.
Instead, give Jeff Hardy the Rumble, give Edge the World Heavyweight Title and let them go at it in a TLC match for Jeff’s first world title (forget Armageddon 2008).
3 2015 - ROMAN REIGNS
This one will go down as the most wrong-headed Rumble booking decision in history. Vince McMahon had a year to build up Roman Reigns for his big Rumble win, but as January inched closer the fans were more and more restless and apoplectic at the thought of him winning. It didn’t help that Daniel Bryan made a surprise return just before the event and declared his intention to win the match. Fans wanted Daniel Bryan in WrestleMania’s main-event just as strongly as they wanted Reigns out of it.
In hindsight we can say Vince made the right call. Reigns vs Lesnar was a great heavyweight slugfest with a hot crowd and had one of the best finishes ever. Bryan would be retired for good within a few months. Hindsight is for losers though; Bryan winning would have been great, as would have his David vs Goliath match with Lesnar.
2 2014 - BATISTA
Speaking of Daniel Bryan, here’s Batista! Obviously in the end it all worked out, and the way WWE told its story (adapting to the near-riotous crowds) made the Road to WrestleMania XXX arguably the best ever. But just because their improvising worked out great, doesn’t mean their original plans were any good. On the contrary, the original plan for Batista vs Randy Orton would have turned WrestleMania XXX (which the whole WWE Network was riding on) into a laughingstock fiasco.
Vince should not have panicked when the SummerSlam 2013 buyrate came in under their estimations. He should have stuck with Bryan, told the story of him being knocked down and climbing back to the top, winning the Rumble and winning at WrestleMania. They managed to get there in the end, and—again---the story managed to come together, but that doesn’t change the fact that Batista winning the Rumble was a bad idea that almost sunk the boat.
1 2002 - TRIPLE H
It’s not just Triple H’s win, which was always uninspiring. It’s the whole WrestleMania X-8, and the previous year’s booking that led to it. Everyone has their fantasy-booking, here’s my condensed idea: Don’t do an InVasion. Split the rosters in 2001, with WCW, ECW and a few key WWE guys on one side and the rest on the other.
Have Austin hold the WWE title as a heel for a whole year. Have WCW GM Ric Flair abuse his power and steal the WCW Title, then be stripped of it and have the Rumble be for the belt. Use the Rumble to kick off the 'Mania feud for Rock and Hogan, and bring back HBK a couple months early for a DX vs nWo (HHH/HBK vs Hall/Nash) feud.
Jericho wins the Rumble and WCW title. Turn WrestleMania X-8 into a big inter-promotional PPV with Austin vs Jericho, title vs title as the main-event.
Fans love to fantasy book, and while we don't always agree on what we should do, we do usually agree when we see one done poorly. Too often, the Royal Rumble has fallen into that category.
Will it again? We'll see.