You bring up a great topic. It's a topic that I think is one of the biggest screw-ups the WWE made in the "New Generation" era. Never having an epic Bret Hart/Randy Savage matchup.
To start off with, I have never been able to understand or support Vince's decision to relegate Randy Savage to being an announcer/lower-card talent in 1993/1994. I get that Vince was pushing younger wrestlers (Hart, Razor, HBK, Diesel, Luger, Undertaker, etc.) and was pushing for a new era, but there was certainly nothing wrong with keeping at least a couple of veterans to help bring up these newer guys and put them over. Randy Savage would've fit the bill perfectly. Savage didn't have to be the No. 1 guy in the company. But he could've very easily been a top heel or babyface that could've gotten anybody over. By 1993/1994, Randy Savage could still go in the ring and he definitely would've been able to keep up with the younger guys. You're talking about the greatest WWE worker of 1986-1992 here. Skill-wise, he certainly didn't go from being the guy who was the champion and carrying the company on his back (like in 1992) to being a commentator and lower-card wrestler (like he was in 1993 and 1994) like his role in the company seemed to state. He deserved way better than he was treated in his last few years. I don't blame him at all for leaving and going to WCW. I don't think Savage had a Hogan-like ego in that he felt he should continue to be the top guy in the company. As long as he was in the upper-mid card to main event level (which he certainly should've been at), just wrestling on the shows, he would've been happy I think.
I mean for example at Wrestlemania X. Besides the now, legendary Ladder Match between HBK and Razor, and the technical classic between Bret and Owen, what was the other match on the show that was pretty darn entertaining and unique and good and memorable? Savage and Crush. Yes, compared to the hardcore matches that would happen later on in the WWE, it doesn't compare, but for 1994, it was a pretty unique and interesting, and decent match. I think if it had lasted longer (it was way too short for my tastes), more attention would be given to that match now. For me, the Falls Count Anywhere match was always the most memorable match at Wrestlemania X besides the Owen/Bret and HBK/Razor encounters. You didn't have matches like the Savage/Crush brawl in the WWE pre-1994. So even though that was like one of the few matches he had in a year's time (he wrestled at Survivor Series 93 as well), Savage still managed to put on an entertaining and memorable matchup. Also check out his matchup with Yokozuna on Raw from just a few weeks before Wrestlemania X. I hadn't watched that matchup in years, but I watched it a few months back on the Savage DVD, and I think it might actually be the best match I ever saw Yokozuna wrestle in (even better than his two Wrestlemania matches with Bret Hart). So if Savage at this time period could've still had good to even great matches with Yokozuna and Crush, then he certainly could've still had some awesome, even, classic matches with guys like Bret Hart, Shawn Michaels, Owen Hart, Bam Bam Bigelow, Lex Luger, Razor Ramon, the Undertaker, etc. Savage could still go at this point, and WWE should've done everything they could to keep him. I understand letting Hogan go. He still wanted to be the main focus of the company and make more money than everyone else. Savage just wanted to be on the show and wrestle. He was an excellent veteran that was maybe just starting to be a bit past his prime (but still very good), and could've really helped elevate the younger talent at the time that was coming along. Vince should've kept him and made him a part of the show.
So, with that said, that brings me back to the topic at hand. Should Bret have won the title from Savage instead of Flair?
I think that's a very interesting scenario, and it might've helped get Bret over more as a legitimate champion than Flair did. As you stated, Savage and Bret were actually good friends, fans of each other's works, and respected each other greatly. Savage would've had no problem whatsoever in getting Bret over. Both since then have stated that they both wished they could've had a program together during Bret's early reigns as champions. And other than the Flair/Hogan matchup that should've happened at Wrestlemania VIII, I think that Hart/Savage was the biggest program/feud that Vince never capitalized on and should've in that era. Bret Hart and Randy Savage would've been epic, simple as that.
However, I wouldn't have built it up to them clashing at Survivor Series 92 with Savage as the champion and Bret winning it then. I agree with the previous poster in that the "shock value" of his win was actually good for him and made his win more exciting. I also have no qualms whatsoever with Bret winning the title from Flair. What WWE messed up on in late 1992, was not capitalizing on having a Hart/Flair program for the title. Part of that might be Ric Flair's fault for not really wanting to work with Bret or put him over. Or it could've been the lack of chemistry they had in matchups on house shows. But if Flair was a "company man" like he's always stated he was, Vince should've pushed a Hart/Flair program on them for the remainder of 1992, then later on built to an epic Savage/Hart feud. Flair and Hart could've worked out the kinks in their in-ring chemistry and with a few month's worths of build up (and practice matches on house shows), they could've probably put on a solid, if not great ppv matchup. Here's what I would've done.
I would continue with the way everything worked out up to October 92. Have Flair win the title from Savage in September like they did. Go forward with the surprise, out of nowhere win by Bret over Flair. It was good shock value and it made everyone stand up and pay attention to Bret. Unfortunately, nothing ever really materialized with this. You had a great opportunity to continue with a big time feud with Hart and Flair over the title and even keep Savage and Razor in the program as their respective allies. I saw a promo on YouTube awhile back highlighting a tag team match the two had at a house show or something, and it was epic to say the least. Flair and Razor talking about how they're going to take Savage and Hart out, and then Savage and Hart retorting back saying they were going to take Flair and Razor out. This could've and should've been the main event for Survivor Series 92. Instead of the Warrior and Savage teaming up against Razor and Flair, it should've been Bret and Savage against Flair and Razor. Yeah he wouldn't have defended the title, but Savage and Flair was still the main feud going on in the company at the time. Razor was being elevated by being associated with Flair. Bret, as the new champion should've been elevated by being in the program with Savage and Flair.
Now of course that would eliminate the now classic match that HBK and Bret had at Survivor Series 92, but you know, what can you do? I mean in reality, other than having a great match what did that event/match do for Bret? At the time Shawn was a mid-carder and new IC champion. It was fantastic for Shawn to be working with the world champion at one of the biggest ppvs of the year (which Survivor Series obviously was at that time) and really made him look great, but how exactly did that look for the new world champion having to wrestle the I-C champion on one of the biggest ppvs of the year? Savage/Warrior (well Savage/Perfect) and Razor/Flair was still the top drawing program for the show and the angle that was getting the most hype and attention. Bret should've been in the top program as he was the new champion. He should've been the main focus. It's kind of the same deal with Benoit/Kane at the Bad Blood 04 ppv being overshadowed by the HBK/HHH Hell in a Cell matchup. The main event should focus on the champion, especially when the champion is a new guy (in the role of being world champion I mean) that the company really needs to get over.
So I would've had Bret teaming up with Savage against Flair and Razor at Survivor Series 92. Give Shawn something else to do. He'll get his time to move up and be elevated. Then after that matchup (in which Savage/Hart wins of course), then you build to an epic rematch between Bret and Flair at the 1993 Royal Rumble. Scott Hall and Bret Hart have both since stated that Razor wasn't ready to be thrust into the main event that early on. His character wasn't over enough yet. I mean I think they still had a good match, but it was kind of risky having two "new guns" going at it in the main event. A Flair/Hart matchup for the title would've been a much better main event. Flair didn't officially leave the company until early February of 1993, so he could've very easily been in the title match at the ppv instead of being in the Royal Rumble matchup for like 10 minutes like he was. Flair should've left the company putting Hart over, not Mr. Perfect. It was nice he put Perfect over of course, but in the grand scheme of the WWE, what good did that really do? WWE didn't end up doing much with Mr. Perfect after that. At least not compared to Bret Hart anyway. Between Survivor Series 92 and Royal Rumble 93, have Flair and Razor attacking Hart on Superstars or Wrestling Challenge a few times. Have them interfere in some matchups, have them do promos with Flair talking about how he's going to take the title back, etc. Have them got at it at the Royal Rumble. Flair loses and puts Hart over again on ppv television as the champion. Whether he wanted to do it or not, Vince should've made him. This alone would've made Hart look stronger. But I'm not done yet obviously
At the same ppv, instead of Yoko winning the Rumble, have Savage win it, like someone else suggested. Have Yoko be the last guy of course so it'll make him look strong and put him over for a future run with the title. Then you have an epic babyface encounter between the Hitman and the Macho Man for Wrestlemania IX. This match alone could've saved the show and made it go from what is generally considered one of the worst Wrestlemanias of all-time, to one of the best (at least in my mind, because I've always loved the setting and theme of the show, it just really needed a great match to put it over the top, which Savage/Hart could've done). Have them wrestle a 20-30 minute back and forth classic babyface-styled matchup, and Hart wins. But don't have him win with the sharpshooter. That's too much of a conclusion. Have him win with a fluke like rollup/pinning combination (ala the match he had with Roddy Piper at Wrestlemania VIII). Have Hart try to shake the Macho Man's hand after the matchup. Savage gets angry and just leaves.
The next night on Raw, have Savage come out and apologize and just say that he was frustrated, yadda yadda, and then have them shake hands. Then have them team up on Raw and help each other out, exist as allies over the next few months, but with subtle hints of tension/jealousy building up on Savage's part. Hart's the young gun "showing" the veteran (Savage) up.
Now comes King of the Ring 93. Now have Bret and Razor as the main event (like what happened in the 1st round matchup at the real King of the Ring 93). Razor should be ready at the point for a main event matchup. Have Savage and Yoko in the King of the Ring tournament. Have them end up in the finals. Mr. Fuji and somebody else (I don't know who lol) is interfering helping Yoko out in the matchup. Hart comes out to help Savage. Somehow Hart ends up costing Savage the matchup and King of the Ring title on accident (steel chair shot/salt in the eyes, take your pick). Yoko gets put over and becomes the King of the Ring (which can eventually lead to a title run if you want). Savage gets angry at Hart for costing him the matchup and the King of the Ring win. But doesn't attack him, yet.
Have Savage push Hart and nearly come to blows with the refs stopping them from fighting. The show ends like that with Yoko celebrating as well.
Then on Raw have Bret apologize profusely, and then they reconcile. Then eventually have them team up in a matchup on Raw (about a week or two later), and then Savage blindsides him and turns heel. Then Savage can go on a big Macho Man like promo talking about how Hart thinks he's the new king of the WWF and the new top guy, well not on his watch. Savage is still the Macho Man and the best, yadda yadda, and challenges Hart for a rematch at Summerslam 93. Have the feud get real personal. Have Savage attack Owen and the Hart family (like what Razor did leading up to their Royal Rumble 93 matchup). Just have Savage become a flat-out nutcase on TV and a real threat to the Hitman. Then at Summerslam 93, have a falls count anywhere, or no DQ brawl/fight/matchup between Bret and Randy Savage.
Hart wins with the sharpshooter and concludes the feud.
I think that would've made for a far more interesting and better 1993, then we got with Hulk/Yoko as champs and Yoko feuding with Luger, don't you think?
To give a final answer to your question. I think Savage could've really done wonders in getting Bret over (Flair could've and should've been made to do better too). If only Vince knew what he had with Savage.
