When do you feel the WWE roster was at its all-time strongest?

LODemolition

Championship Contender
For me, I'll say it had to be 1991-92. The roster at this point in time was just stacked beyond belief. This is when they got Ric Flair in his prime, The Undertaker's streak was only beginning, Bret Hart's singles career was also just beginning, and the Road Warriors had arrived to compete in an already amazing tag team division.

The only major losses that come to mind are Rick Rude (who left in October of 1990) and Dusty Rhodes (who left after the 1991 Royal Rumble), but I think we can all agree that Dusty didn't quite fit in.

Here is their roster at the time and if I'm forgetting anyone, please don't hesitate to correct me.

Main eventers/upper card talent: Hulk Hogan, Ultimate Warrior, Randy Savage, Sid Justice, Ric Flair, The Undertaker, Mr. Perfect, Sgt. Slaughter

Midcard talent: Bret Hart, Roddy Piper, Big Bossman, Ricky Steamboat, Davey Boy Smith, Kerry Von Erich, Ted DiBiase, The Mountie, Honky Tonk Man

Lower card talent: Virgil, Jim Duggan, Tito Santana, Greg Valentine, Koko B. Ware, Jimmy Snuka, Jim Neidhart, Irwin R. Schyster, Warlord, Barbarian, Col. Mustafa, Haku, Rick Martel, Bad News Brown

Tag teams: Legion of Doom, Bushwhackers, The Rockers, Demolition, Powers of Pain, Nasty Boys, Natural Disasters, Beverly Brothers, Power & Glory, Orient Express

So what could have been better or at least what would I have done differently? For starters, I never would have split up Demolition or Powers of Pain. 2 of my all-time favorite teams that had no business going their own ways. Who didn't see Repo Man failing from a thousand miles away? Out of these 5 guys, the Warlord was the one who had the look to actually become something on his own, but regardless he and Barbarian were excellent together.

Matches/feuds we missed out on? As great as the roster was, there were a lot if you ask me. Wrestlemania VII and VIII should have been among the best we've ever seen. The 1992 Royal Rumble will always be the greatest rumble match of all-time. So greatly played out. SummerSlam 1991 could have been so much better than it was. I know hindsight is always 20/20, but Ric Flair, Jake Roberts, The Undertaker, Sid Justice and the "retired" Randy Savage weren't even on the card for this one. Survivor Series 1991 always stands out as one of my favorites with The Undertaker tombstoning Hogan onto the steel chair placed in the ring by Ric Flair to win his first WWE Championship. The terrific feud between Randy Savage and Jake Roberts and the cobra biting Savage while he was tied in the ropes. These are some of my favorite memories from when I was a child. But as I said, it just feels like there was always more they could have done with the talent they had available to them.

Here is my short list of matches/feuds that never were bit always should have been:

Hulk Hogan and Mr. Perfect or Jake Roberts at SummerSlam '91 (WWE Championship)
Hulk Hogan vs Ric Flair at WrestleMania VIII (WWE Championship)
"Macho Man" Randy Savage vs Jake "The Snake" Roberts at WrestleMania VIII (Steel Cage or Career Match)
Legion of Doom vs Demolition at WrestleMania VII (Tag Team Championship)
Bret "Hitman" Hart vs Ricky "The Dragon" Steamboat at SummerSlam 1991 (Intercontinental Championship)
Ultimate Warrior vs The Undertaker or Jake Roberts at SummerSlam 1991
"Rowdy" Roddy Piper vs Ric Flair at SummerSlam 1991
Legion of Doom vs Powers of Pain or The Rockers at SummerSlam 1991 (Tag Team Championship)
Mr. Perfect vs Ricky Steamboat or Davey Boy Smith at Royal Rumble 1991 (Intercontinental Championship)

There are plenty of other matches/feuds I would've loved to have seen and won't even be particular about the time:

Randy Savage vs Mr Perfect
Ricky Steamboat vs Ric Flair
Ultimate Warrior vs Sid Justice
Undertaker vs Sid Justice
Ultimate Warrior vs Ric Flair
Randy Savage vs Sid Justice
Roddy Piper vs Randy Savage
The Rockers vs Demolition
Demolition vs Nasty Boys
Demolition vs Natural Disasters
Randy Savage vs Bret Hart
Randy Savage vs Undertaker
Ricky Steamboat vs Jake Roberts

Oh what could have been...
 
02-03 had a pretty insanely stacked roster:

Austin, Rock, Taker, Goldberg, Michaels, Lesnar, HHH, Angle, Flair, Eddie, Edge, Jericho, Benoit, Kane, Show, The Dudleys, The Hardy's, Booker, Christian, RVD, Steiner, Mysterio,... not to mention up and coming names like Cena, Orton, and Batista.

Sure the Divas and Tag divisions sucked, but I would definitely say this was the roster that had the most accumulated star power without a doubt.
 
Today's roster by far. They just have the factors working against them in their overexposure in an industry that hasn't innovated enough for today's performers to look as talented as they really are.

They also aren't popping steroids as much as they should.
 
I can't say which year was the strongest talent-wise for the WWF--I'm far too lazy to do the amount of research I'd need to do to give a definitive answer. While I can't say for certain that it's the best year talent-wise, I can pimp the starpower of the WWF in 1984.

During the first half of '84, they still had Bob Backlund, a man who had just recently held their World Championship for six years. They also had Bruno Sammartino, who holds the record for their longest World Championship reign and also happens to be considered one of the greatest wrestlers of all-time. Hulk Hogan-possibly the most famous grappler in history-arrived and became a mainstream phenomenon, embarking upon another of the WWF's greatest title reigns. To add to that list of great champions, they employed Andre the Giant, who was the biggest attraction in the world of wrestling.

There were also terrific foils for the above mentioned superstars. Rowdy Roddy Piper was one of wrestlings greatest ever heels and soon would be instrumental in the success of the historic first Wrestlemania. Big John Studd was a good opponent for Andre and Ken Patera and Dr. D were some of the most hated wrestlers of the time. The Iron Sheik, another World Champ, helped propel the popularity of Slaughter and Hogan. He then teamed up with the incoming Nikolai Volkoff, with the team becoming multiple World tag champs in early '85.

The midcard was loaded with talent as well. Greg Valentine and Tito Santana are two of the all-time greatest Intercontinental champions. The British Bulldogs, one of histories best teams, arrived and the young team of Barry Windham and Mike Rotundo was loaded with promise. Sgt. Slaughter, Jimmy Snuka and JYD were some of the most popular wrestlers in the country. Paul Orndorff battled Hogan early in the year and later became of one of Hogan's greatest rivals, selling massive amounts of tickets.

There are tons of stars I haven't even mentioned yet, guys like Adrian Adonis, the always underrated Bob Orton, Jr., Dick Murdoch, Jesse Ventura, the newly arriving Bret Hart, Blackjack Mulligan, and the Briscos. The WWF had also acquired Gene Okerlund to handle interviews and had some of the most successful managers ever with Bobby Heenan, "The Guiding Light" Lou Albano, Classy Freddy Blassie and The Grand Wizard on board.

I'm sure there will be some convincing arguments for many other years, but I think it will be difficult to find any that can match the legacies and sheer star power of Hulk Hogan, Bruno Sammartino, Andre the Giant and Bob Backlund. Those guys have combined to hold the title over twenty-two years!
 
When you think about it, and admitted it's probably a bit biased; but the current day WWE roster is really strong and even the weaker wrestlers tend to have a redeeming feature to them.

You have great wrestlers not just in the main event, but also in the midcard to; people like Cesaro, Kevin Owens, A.J Styles, John Cena, Seth Rollins, Roman Reigns, all of which have proven to be phenomenal workers that can be counted on to have a great match.

Admittedly the booking may not be the best for everyone, but even in other rosters mentioned as 'the strongest' such as 2002-03 and 1991-92 they probably had people complaining about why this person wasn't world champion or why that guy was getting pushed over everyone else.
 
From an in-ring talent perspective, the roster just seems to get better and better as time goes on. The 2017 roster is absolutely stacked with some of the best wrestlers in the world, all of whom come in all sorts of different shapes and sizes, from the top of the card to the bottom. Big guys like Braun Strowman and Samoa Joe are delivering like they're half the size and are changing the ways in which big guys should be perceived in WWE. The top stars of the company, guys like John Cena, AJ Styles, Roman Reigns and Seth Rollins, are consistently delivering top quality matches and are certain to deliver match of the year-worthy competition when the time is right. And as you go down the roster, it continues to impress.

From the perspective of legacy, and what particular stars meant at that time and what they would come to be, I suppose that the 1991/92 roster was indeed very stacked. The mid-card in particular had a plethora of talent, some very new and exciting, others a little more experienced and perhaps heading out the door in one way or another. But it was a very solid line-up. I agree that the 2002/03 roster was, in retrospect, very stacked too, though I'm not so sure which of the two will have a bigger legacy once the latter is as aged as the former.

I don't know if this truly qualifies, but I'd also argue that the roster in the very late 1990s, heading into the end of the Attitude Era, was quite special. Top stars like Stone Cold, The Rock, Triple H, Mick Foley, Undertaker, Kane, even Kurt Angle and Chris Jericho to a certain extent, are some of the best of all-time and all collided at the same time in a very short period. The shows were written in a way in which even the most irrelevant seeming guys, like say a Perry Saturn for old time's sake, would seem like a very important deal in whatever kind of way he was featured. That's part of what I think made that era very special, because everyone seemed to play an important enough part that they are still remembered, even when they probably wouldn't be as so in other times. I think it all depends on perspective and what you value in a roster.
 
Another match/feud I can't believe I forgot to include is the Hart Foundation vs Legion of Doom. I feel like the 1991 Royal Rumble or WrestleMania 7 would've been an opportune time.

Also, I've always wondered why in the world the Hitman and Anvil never feuded after they went their separate ways in 1991. They lost the tag team championships to the Nasty Boys at WM7, had one more match in July, and then of course Bret quickly was pushed on his own and won the IC Title at SummerSlam. It seems to me they should have turned Neidhart heel and they could have spent the next 3 months in a feud, maybe longer. I know Hennig was having back issues and they needed to get the title off him, and Bret was their guy, but that doesn't explain why they never took advantage of a good storyline opportunity in the months prior to SS. Maybe there is more to it that I'm not aware of, but I'm just confused why they wouldn't go the traditional route of having former tag team partners square off.
 
Another match/feud I can't believe I forgot to include is the Hart Foundation vs Legion of Doom. I feel like the 1991 Royal Rumble or WrestleMania 7 would've been an opportune time.

Also, I've always wondered why in the world the Hitman and Anvil never feuded after they went their separate ways in 1991. They lost the tag team championships to the Nasty Boys at WM7, had one more match in July, and then of course Bret quickly was pushed on his own and won the IC Title at SummerSlam. It seems to me they should have turned Neidhart heel and they could have spent the next 3 months in a feud, maybe longer. I know Hennig was having back issues and they needed to get the title off him, and Bret was their guy, but that doesn't explain why they never took advantage of a good storyline opportunity in the months prior to SS. Maybe there is more to it that I'm not aware of, but I'm just confused why they wouldn't go the traditional route of having former tag team partners square off.

I'm pretty sure neidhart was fired for throwing a camera at someone after Vince told him they were breaking up the team.

Plus neidhart has never been strong in singles...

who?
 
Wikipedia says Neidhart wasn't fired until early 1992 for misconduct. I agree he was never strong on his own, but that goes for plenty of guys who were in tag teams and split up. There's more often than not a break out star of the team and then the "Jannetty" of the team. It just would've been a much better use of him to help put Bret over and be a stepping stone on his way to the IC Title.
 
Wikipedia says Neidhart wasn't fired until early 1992 for misconduct. I agree he was never strong on his own, but that goes for plenty of guys who were in tag teams and split up. There's more often than not a break out star of the team and then the "Jannetty" of the team. It just would've been a much better use of him to help put Bret over and be a stepping stone on his way to the IC Title.

Quite simply because that's not how things were done regularly back then. And to be honest, I wish today were the same, as we get tag teams splitting far to frequently and FAR too soon. I'm sure I may be missing some, but off-hand the only teams I can think of that split BEFORE the Hart Foundation and immediately feuded were the Twin Towers (Boss Man turning face) and Strike Force (a means to get the titles on Demolition, and an expertly done heel turn by Martel.)

I'm not counting Demolition as it took Crush over a year to start feuding with the Repo Man, and to my knowledge it was never mentioned on tv that they used to partner.

Add to that the fact already mentioned that Neidhart wasn't a great singles wrestler - indeed, he was put on commentary for a while before teaming with Owen Hart as the New Foundation, with only a handful of televised singles matches after the Hart Foundation split.

I always feel bad for Jannetty. His name has become wrestling parlance for the weaker tag team member who fades into obscurity after a split, but actually this is very revisionist. Watch early Raws on the Network and you will see a Jannetty who is heavily featured, in some of the best tv matches in 1993 and early 1994, won both the Intercontinental and Tag Titles, and only actually got taken off tv after a jobber sued WWE and Jannetty after breaking his neck in a botched Rocker Dropper by Marty a couple of years earlier.

Contrast that with Neidhart, who never really did anything of note after splitting with Bret, and who's comebacks usually lasted only a handful of months, and surely the failed tag team member should be known as the "Anvil" of the team?
 
Contrast that with Neidhart, who never really did anything of note after splitting with Bret, and who's comebacks usually lasted only a handful of months, and surely the failed tag team member should be known as the "Anvil" of the team?

Haha, excellent point. Marty does get a raw deal. If he hadn't gotten fired before the '92 Rumble, we could still be talking about him and Shawn having one of the greatest feuds we've ever seen. I guess his name gets associated with failure because he faded away and was never really heard much from again rather than Neidhart who popped back in from time to time to stay somewhat relevant in WCW and the new Hart Foundation.
 
from in ring talent and star power perspective 2001-2004 id say, you had Goldberg, nWo, Hogan, HHH, Austin, Rock, Taker, Booker, DDP, Guerrero, Angle, Benoit, Jericho, Rey, Brock, Big Poppa Pump, Foley, Flair, HBK, Kane, Cena, Orton, Batista, Big Show; the list goes on and on... not only established names but the true next generation was peppered in there also. It was the best time for dream matches as well as 5* matches
 
Again, i think it all depends what you look at. Personally, i think 87 through 91 was probably their strongest mostly because when you look at their roster at the time. All the division were covered. Everybody had a job to do and did it well. You really didn't need to be in the title picture to be over at the time. You look at the list of babyface that we're super over at the time and didn't win a championship. Guys like Duggan, Rhodes, Piper, Beefcake & roberts we're all super over with the crowd and didn't need to be put in a title program to stay over. You also a awesome tag team division at the time with teams like the hart foundation, demolition, the rockers, the rougeaus & the bushwhackers and later on the nasty boyz, the natural disasters and legion of doom. Tag team wrestling was made important back then.

Plus you had some great talent on the heel side to go against Hogan. Guys like Andre, Dibiase, earthquake & mr. perfect all help made hogan the huge star he became.

If it wasn't for those guy back from that era, i don't think we would still have a WWE in this or any form right now, they are the guys that made the WWE what it is today and that's why i think they are the strongest roster.
 
My top choice would be 1991 when they had names on their roster like...
Hulk Hogan, Ric Flair, Roddy Piper, Ultimate Warrior, Randy Savage, Undertaker, Andre The Giant, Sgt Slaughter, Mr Perfect, Kerry Von Erich, Dusty Rhodes, Dustin Rhodes, Ted Dibiase, Hawk, Animal, Jake Roberts, Boss Man, Bret Hart, Davey Smith and Shawn Michaels.

My 2nd choice would maybe be 2002 with names like....
Steve Austin, The Rock, Hulk Hogan, Ric Flair, Undertaker, Kurt Angle, Brock Lesnar, Randy Orton, Batista, John Cena, Shawn Michaels, Triple H, Kane, Big Show, Kevin Nash, Scott Hall, X-Pac, Chris Jericho, Rob Van Dam, Booker T, Goldust, Dallas Page, Edge, Christian, Bubba Dudley, Devon Dudley, Ron Simmons, Bradshaw, Matt Hardy, Jeff Hardy, Rikishi, William Regal, Rey Mysterio, Chris Benoit and Eddie Guerrero.
 
I think that when it comes to All-Time strongest in the ring, it's today's roster. The wrestling in today's age is wrestling. instead of very short matches, the wrestlers put on nicely timed matches and they usually are always good. AJ Styles, Kevin Owens, Samoa Joe, Seth Rollins, Shinsuke Nakamura, Finn Balor, Cesaro, Sami Zayn, Neville, The Hardys, Chris Jericho put on fine matches and there's other talent in either NXT or that's just not being used well that can go in the ring too.

Now when it comes to star power and used correctly, then it should be during the era when Goldberg was in WWE (his first run), but i'm more into watching good matches and while it's great seeing star power or legends, they arent as good as the wrestling.

Even Brock in his short matches are entertaining because his matches actually feel like it's real because of how short he sometimes wins or loses.
 
1997

Beginning to transition into the Attitude Era.

Bret Hart, HBK, Stone Cold, Triple H, The Rock, Taker, LOD, New Age Outlaws. Even Golddust, and Mankind were getting pretty over.
 
I guess it depends how you're viewing the talent and what makes a "big name"... Personally, I don't think later rosters are as "stacked" as there may be more ex WWE champions but the value of titles diminished over time so there's a point where anything upwards of 12 former champions are on the roster at any one time (Cena, Batista, Edge, Taker, Jericho, Orton, Kane, Rey, Miz, Triple H, Booker etc...)

For me the earlier eras are more stacked as they had more legit star power that was "cherry picked" rather than WWE being the only real option.

1987 is a strong year... you had Hogan and Harley Race, two of the top champions of the past decade... even past his prime, Harley was still a draw. Add to that:-

Andre
Piper
Steamboat
Savage
Ted DiBiase
Jim Duggan
Superstar Billy Graham & Pedro Morales (early 87 only)
Iron Sheik
Muraco
Rick Rude (from middle of year)
British Bulldogs
Hart Foundation
Orton & Orndorrf
Bam Bam Bigelow

That is one hell of a roster of established, fresh and future talent and thats before you add in the Beefcake's, Butch Reed's and Jake Robert's of the world.

Spring 1989- to fall 90 was arguably the peak however....

You had:-

Former/Current World Champs

Hogan, Warrior, Savage, Kerry Von Erich, Dusty Rhodes, Andre & Ted DiBiase (technically), Rick Martell & Curt Hennig (AWA) & Ronnie Garvin

Main Event level talents who won a title later

Rude, Slaughter, Piper, Barry Windham

Future Main Eventers

Bret Hart, Shawn Michaels, Big Bossman, Owen Hart/Blue Blazer, Davey Boy Smith

Top Level Talents

Jimmy Snuka, Masked Superstar/Ax, Arn & Tully, Bad News Brown, Powers of Pain

Again, add your Jake's, Honky Tonk Man's, Greg Valentine's and Power and Glory's to that and you have a hell of a roster.


That is an insane level of talent for the WWF roster to have at one time with guys like Windham being "lost in the shuffle" and much of the WWF's future being hidden in plain sight in the tag/lower card divisions. Talent had gotten over either in the WWF or elsewhere and didn't need titles to do it. Someone like Kerry Von Erich might only have won the IC in the WWF but the star power was clear, just like how a Rick Martel was nowhere near the WWF title...but was always a former World Champ in how he came across..

Talent can't do that today... they need 15 title reigns for legitimacy... in that earlier era, the title rewarded legitimacy, didn't create it.
 
I would say around the time of the 1992 Royal Rumble.

You have Hogan and Flair, the 2 most iconic stars of the modern era (at a time when they were new to each other), there are future legends in Bret, Shawn, Undertaker.... established legends such as Randy Savage, Piper, Sgt Slaughter, Iron Sheik.... Jake Roberts at his evil best, though inactive Curt Hening would soon be wrestling again, the most iconic tag team of all time in LOD, and you have a solid array of midcarders such as Davey Boy, Owen, Dibiase, Kerry Von Erich, Santana, Martel, Boss Man, Mountie, , Valentine, Earthquake, Snuka, Rotundo .... and even the Nasty Boys, Tatanka, Neidhart and Sid had their moments.

I can't believe that by 1993, how much of that roster was depleted.
 
Rather than listing the most stacked roster in WWE history, with the top being candidates (84, 87, 91, 92, 98-99, 02-03, current) already being mentioned, I"m gonna instead list what I feel is the most overlooked and underrated/stacked roster in the history of the WWE, which hasn't been mentioned yet.

That roster is none other than the roster of 1993.

Yes, a lot of top stars had left in 1992, but here's a list of wrestlers that were on the active roster of the WWE at some point in 1993 (I'll say more than 2 months), not in any particular order (stature, level of card, etc).


Hulk Hogan, Randy Savage, Bret Hart, Shawn Michaels, Undertaker, Ted Dibiase, Curt Hennig, Yokozuna, Lex Luger, Bam Bam Bigelow, Marty Jannetty, Razor Ramon, Diesel (though he didn't wrestle much), 1-2-3 Kid, Jerry Lawler, Doink the Clown (Matt Borne), Crush, I.R.S., Tatanka, Owen Hart, Rick Martel, Giant Gonzalez, Bob Backlund, Papa Shango, Tito Santana, Hacksaw Jim Duggan, The Steiner Brothers, The Smoking Gunns, The Natural Disasters, the Headshrinkers, The Heavenly Bodies, The Quebecers, etc.


I'd say that's a pretty darn stacked roster. Sure WWE lost a lot of big stars in 1992/very early 1993 like Roddy Piper, Jake Roberts, Ultimate Warrior, Davey Boy Smith, Sid, the Big Boss Man, and Ric Flair, but they made up for it by either bringing in and pushing younger, fresher talent like Yokozuna, 1-2-3 Kid, Razor Ramon, Diesel, the Smoking Gunns, the Headshrinkers, or bringing in big names from other companies for the first time, or the first time in awhile like Lex Luger, the Steiner Brothers, Jerry Lawler, and Bam Bam Bigelow. Yeah, I'd agree the combination of Piper, Flair, Roberts, Warrior, Bulldog, Sid, and Boss Man is a bigger group of talent, but Hall, Nash, Luger, Yoko, Lawler, the Steiners, and Bam Bam is a pretty darn good group of talent too.


The problem for the WWE in 1993 was that they just didn't have very good direction as a company. The mass exodus of talent of the Hogan era that occurred 1992-mid 1993, plus the steroid trial I think pushed WWE to feel that had to get rid of any remnants of the Hogan era and push forward a whole new generation of talent, which they tried to do with Luger, Yoko, Bret, HBK, Hall, Nash, Taker, 1-2-3 Kid, etc. But I think WWE going so heavy on new talent kind of also contributed to some fans from the Hogan era turning away from either wrestling as a whole, or eventually WCW. But WWE still had tremendous talents from the Hogan era right on their fingertips to use and push to the top to help the younger talent become more established. The main three I'm talking about are Randy Savage, Ted Dibiase, and Curt Hennig. This would've been the time for Dibiase and/or Hennig to finally get the world title reigns they long deserved. And they were established heels and the among the best heels of their era. They would've made for great adversaries for Bret and Luger as the top two babyfaces, not to mention Randy Savage who could've been either the top face to anchor the company around until Bret and Luger got more established, or they could've made him the top heel for Bret and/or Luger to go after.

They ultimately went with Yokozuna as the monster heel, but they also had Bam Bam Bigelow who could've filled that role as well and IMO would've been better as he was more mobile and could have better matches than Yoko. Hall and Nash, along with Marty, HBK, and 1-2-3 Kid were perfect to anchor the mid-card like they did.


WWE I feel could've stalled the epic fall they went down at least for another year as they still had some of the biggest names in the world over the previous 10-15 years in their company (Hogan, Savage, Lawler, Dibiase, Hennig, Backlund, Luger, etc.). They pushed too hard towards younger talent, (somewhat like WCW tried to do in 2000) and it alienated some fans. They didn't have the right balance of keeping the established guys as top guys (again Savage, Dibiase, and Hennig beings the keys here) while establishing the younger or newer talent (Hart, Taker, HBK, Razor, Yoko, Luger, etc.).


I think if WWE could've had better direction and done more with the talent they had, 1993 would maybe remembered as the last great year of the WWE in the 90's period (before the Attitude Era reignited the company), instead of the first year of the downfall, like it is today.
 
93 was an interesting one as it was one of the "oil changes" that WWF did from time to time, notably in 87. 89 and 1991 into 92. Between WM3 and 4 you had whole swathes of the roster replaced and 92 into 93 was the first one that didn't quite pay off as WWE hoped.

For the first time, there were unproven names and workers replacing big ones... When guys like Orndorff and Shiek disappeared in 87, they were brigning in guys like DiBiase, Duggan and Rude, who had drawn elsewhere. Likewise in 89, when guys like Hennig and The Rockers came in.

This oil change took longer and often seemed reactionary rather than well planned. For the first time they weren't "cherry picking" who to bring in but seemingly just bringing people in en masse to cover lost talents.

Rude walked and they brought Luger in eventually in his role... on paper that should have worked but it didn't. The Steiners shouldn't have been able to miss but somehow they did and guys like Yoko, Razor and Tatanka had potential but were very much unproven and thrust into top positions when fans hadn't even gotten used to them.

Heading into 93, you had a LOT of talent on the roster, but few of them were actually being used correctly or it was a false position. Flair was leaving, Lawler was facing his legal trouble, Hennig was already looking for the Lloyds payout again and DiBiase and Hogan weren't planning on sticking around.

93 has the most missed potential of any roster WWE has ever had, mainly because of Vince's decisions. Who let's Flair lose a career match on RAW? even if you are trying to launch a show... Who benches Randy Savage as a commentator when trying to get a champ like Bret Hart over? Who allows a talent to outright lie about fellow workers and keep the belt on him?

Admittedly the steroid issues were a big problem, but Vince being Vince was also a massive problem that stopped that roster from fulfilling the potential it had and made that "oil change" the start of a downward spiral rather than a boost like the others.

Just think of what we DIDN'T get at Mania 9 that could have been...

Bret v Savage for the title
Flair v Perfect Career match
Jannetty v Michaels for the IC (or Tatanka winning it)
Steiners v Money Inc.
Hogan vs Gonzales
Yoko v Taker
Lex and Razor v Legion of Doom

How different would it have been if Vince had kept the talent around and booked THAT show?
 
For me, I'll say it had to be 1991-92. The roster at this point in time was just stacked beyond belief. This is when they got Ric Flair in his prime, The Undertaker's streak was only beginning, Bret Hart's singles career was also just beginning, and the Road Warriors had arrived to compete in an already amazing tag team division.

The only major losses that come to mind are Rick Rude (who left in October of 1990) and Dusty Rhodes (who left after the 1991 Royal Rumble), but I think we can all agree that Dusty didn't quite fit in.

Here is their roster at the time and if I'm forgetting anyone, please don't hesitate to correct me.

Main eventers/upper card talent: Hulk Hogan, Ultimate Warrior, Randy Savage, Sid Justice, Ric Flair, The Undertaker, Mr. Perfect, Sgt. Slaughter

Midcard talent: Bret Hart, Roddy Piper, Big Bossman, Ricky Steamboat, Davey Boy Smith, Kerry Von Erich, Ted DiBiase, The Mountie, Honky Tonk Man

Lower card talent: Virgil, Jim Duggan, Tito Santana, Greg Valentine, Koko B. Ware, Jimmy Snuka, Jim Neidhart, Irwin R. Schyster, Warlord, Barbarian, Col. Mustafa, Haku, Rick Martel, Bad News Brown

Tag teams: Legion of Doom, Bushwhackers, The Rockers, Demolition, Powers of Pain, Nasty Boys, Natural Disasters, Beverly Brothers, Power & Glory, Orient Express

So what could have been better or at least what would I have done differently? For starters, I never would have split up Demolition or Powers of Pain. 2 of my all-time favorite teams that had no business going their own ways. Who didn't see Repo Man failing from a thousand miles away? Out of these 5 guys, the Warlord was the one who had the look to actually become something on his own, but regardless he and Barbarian were excellent together.

Matches/feuds we missed out on? As great as the roster was, there were a lot if you ask me. Wrestlemania VII and VIII should have been among the best we've ever seen. The 1992 Royal Rumble will always be the greatest rumble match of all-time. So greatly played out. SummerSlam 1991 could have been so much better than it was. I know hindsight is always 20/20, but Ric Flair, Jake Roberts, The Undertaker, Sid Justice and the "retired" Randy Savage weren't even on the card for this one. Survivor Series 1991 always stands out as one of my favorites with The Undertaker tombstoning Hogan onto the steel chair placed in the ring by Ric Flair to win his first WWE Championship. The terrific feud between Randy Savage and Jake Roberts and the cobra biting Savage while he was tied in the ropes. These are some of my favorite memories from when I was a child. But as I said, it just feels like there was always more they could have done with the talent they had available to them.

Here is my short list of matches/feuds that never were bit always should have been:

Hulk Hogan and Mr. Perfect or Jake Roberts at SummerSlam '91 (WWE Championship)
Hulk Hogan vs Ric Flair at WrestleMania VIII (WWE Championship)
"Macho Man" Randy Savage vs Jake "The Snake" Roberts at WrestleMania VIII (Steel Cage or Career Match)
Legion of Doom vs Demolition at WrestleMania VII (Tag Team Championship)
Bret "Hitman" Hart vs Ricky "The Dragon" Steamboat at SummerSlam 1991 (Intercontinental Championship)
Ultimate Warrior vs The Undertaker or Jake Roberts at SummerSlam 1991
"Rowdy" Roddy Piper vs Ric Flair at SummerSlam 1991
Legion of Doom vs Powers of Pain or The Rockers at SummerSlam 1991 (Tag Team Championship)
Mr. Perfect vs Ricky Steamboat or Davey Boy Smith at Royal Rumble 1991 (Intercontinental Championship)

There are plenty of other matches/feuds I would've loved to have seen and won't even be particular about the time:

Randy Savage vs Mr Perfect
Ricky Steamboat vs Ric Flair
Ultimate Warrior vs Sid Justice
Undertaker vs Sid Justice
Ultimate Warrior vs Ric Flair
Randy Savage vs Sid Justice
Roddy Piper vs Randy Savage
The Rockers vs Demolition
Demolition vs Nasty Boys
Demolition vs Natural Disasters
Randy Savage vs Bret Hart
Randy Savage vs Undertaker
Ricky Steamboat vs Jake Roberts

Oh what could have been...

Ric Flair vs Ultimate Wsrrior did happen, several times, they feuded ptetty much non stop from July (SummerSlam build up) through November (when Warrior was besten up by Flair/Hall to explain his leaving WWE), interupted only by Flair's injury time off.
 
This is too much of an open ended question. Meaning that context of society is important. I.e. It's a much more TV driven industry today vs House shows/live event in the 80s.

Then you got 'star' power vs in-ring technical power. Obviously technical skills has gotten much better but under the 80s/early 90s WWF, there was still a form of the territory system which a Darwinian survivalist approach was taken. Only the top guys made it up and out into the WWF, meaning they were way more experienced and established. Today, you have work-in-training annointed ones.

That said, I'm biased too because wrestling is memorable. But I will say the original Hulkamania run era. Around WM 1-3 time. Where they would run 3 house shows and sell out all. 84 is included. You had Andre in his last 'prime', Orndorff, Savage, Snake, Steamboat, Tito, Hammer in their Prime (sure some were around in 92, but not in their physical prime). As well as types like the Junkyard Dog, Don Muraco, Harley Race, Black Jack Mulligan, Adrian Adonis, Bob Orton. Then the tag team. Killer Bees were always underrated IMO, Rougeaus, Bulldogs, Hart Foundation, Shiek and Volkoff, a bit later, Demolition, Islanders. Bundy and Studd as the Monster heels. Then you have all the colorful managers. Of Course Hogan and Piper. Legends like Snuka and of course Sammartino is up there too though they largely stopped wrestling during this time. The 87 Survivor Series really showed what it was about.

And most of all, there was a innovation and unpredictably about it. The early SNMEs were just tense and very well booked. From a name perspective, agreed that 1992 (WM 8) is also tops. But that old school group, what they lacked vs today's athleticism, they more than made up for in wrestling experience and just knowing how to work a crowd.
 

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