Everyone knew Hogan would win at Bash At The Beach because You dont sign Hogan, bring him and have him lose. It was hardly a squash match, I thought it was pretty even, lasted just under 25 minutes. No one on planet earth thought Savage would win at WM 5 but it was a huge match.
That said, the heat from Flair's Royal Rumble win, coupled with the whole "2 best champs in wrestling" idea would have made Hogan-Flair at WM 8 huge, rivaling Hogan-Andre and eclipsing all of Hogan's other WM matches. Flair was the first wrestler in the Vince Jr era that was actually promoted as having had a career outside WWE, an "international champion" who "wrestled around the world". That was a huge admission by WWE standards in the pre Monday Night Wars era.
Personally, although the whole 60 minute "beat the whole WWE" Rumble win was a dominating, impressive way to finally crown him champ, I always thought they should have had Flair go over Hogan clean at RR to win the belt. Have Hogan disappear for awhile, reeling from the loss. Flair goes on a rampage, not just winning matches but beating down opponents, all the time proclaiming himself "The Perfect Champion" and the man who ended Hulkamania (remember Curt Henning & Bobby Heenan were his managers). Finally, maybe at a Sat Nite Main Event after another screwjob win and subsequent beatdown of some fan favorite Flair is confronted by a returning Hogan who triumphantly beats up the champ and declares himself back.
Hogan would reveal in interviews that he didnt know how to handle the RR loss, he thought maybe he'd lost it, that after all these years Flair was better, but he had to return because of the mockery Flair was making of the title and the company, that Hulkamaniacs dont quit and Hogan wasnt going to quit and let down his fans. Of course Flair would initially duck Hogan, eventually agreeing to face him for the title on two conditions. 1st, it happen at WM so all the world can see it, 2nd if Hogan loses he leaves WWE forever.
The match would be set, playing on the whole NWA-WWE dynamic with die hard fans, utilizing the old Heenan-Hogan dynamic, Heenan finally had the horse to beat Hogan & bring him a title, could he finally end Hulka-mania once and for all, and finally if Flair wins again he is entrenched as Greatest Champion Of All Time, hands down, but could he do it at WM, not only the bigest show in wrestling but Hogan's personnal highlight film of career defining moments ? With that set up WWE & McMahon would have gotten the proverbial Match Of The Century. Of course Hogan wins, ending Flair's reign of terror, saving his career, proving the "power of Hulkamania" and quite possibly setting up the rubber match at SummerSlam, possibly in a cage or with No DQ rules.
Now in reality there were unconfirmed stories that Hogan didnt want to lose to Flair, the reason for his RR victory, about as impressive a win as he could get without beating Hogan. Later, plans were changed due to the federal steroid investigation and WWEs decission to distance themselves from Hogan & Piper and anyone else who might be a principal in the case or have a drug problem after WM (the reason for the hastily put together "retirement angle" and match vs Sid) and with that the Dream Match was off. Im not how many fans remember that WWE TV ran a "fan poll" where you could vote for Flair's WM opponent from the Top 4 Contenders (Hogan, Sid, Piper, Savage) and Hogan won, WWE TV ran with Hogan-Flair for 2 weeks before they accelerated the Hogan-Sid feud and Savage was chosen for the title matc