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