I agree with the following: See there's one aspect people aren't grasping with all this - some have touched close, but the reality is that Vince really was in last chance saloon financially when he asked Bret to go to WCW. He'd tried everything he knew in his comfort zone to turn the company around and it hadn't work, leaving the raunchy, Attitude direction as in reality, a last throw of the dice. Vince abandoned it and went back to his comfort zone first chance he got... marketing to kids.
As for Bret and the 20 year deal, I think even then Vince knew the writing was on the wall and the deal would never actually be honored in full. Either the company was gonna go under or Bret would eventually throw his toys from the pram and they'd negotiate a settlement.
What Vince did was offer Bret a win/win (in his mind) get pretty much the same money as the 20 year deal in a shorter space of time with WCW and it got the increasingly whiny (Wrestling With Shadows watched today shows Bret in a pretty negative light) and intransigent star who would have eventually caused a Montreal situation regardless.
Had he stayed, I don't think WWE would have been going "under as such" but I think Bret would have inadvertently damaged their success. WWE was able to create at least new main event star EVERY Year for the next decade except for 03 when Goldberg took that slot. Look at the list below... had Bret stayed for any period of that 20 year contract, one or more of those pushes couldn't have happened. He was already protecting his "spot" despite his claims that he'd drop to "anyone but Shawn" in 97... had the issue not been with him it might have been with the greener Rock, or not wanting to lose to Chris Jericho or Triple H who he didn't respect... or he'd have forced them to give Owen that title run at some point.
98 - Austin & Rock
99 - Foley & Trips
00 - Kurt Angle & Big Show
01 - Chris Jericho
02 - Brock Lesnar
04 - Eddie G, Orton, Benoit & JBL
05 - Cena & Batista
06 - Edge, RVD, Rey
There's also the possibility that signings would have been different and people jumping ship would not have done so. Someone like Jericho might have been excited by being able to face Bret in WWE... but they equally might have been wary that they'd be second string and not get the chances if he lived up to his increasing rep.
Remember word would filter through to WCW about how Bret was via the Kliq... they would only have "one side" of the story perhaps, but much of Bret's actions caught on camera on Wrestling With Shadows would have unnerved some talents on the way in. "Is he gonna power play us like The NWO do..." would have been a factor in some guys not going to WCW or leaving.
Would Owen be alive? Who knows - Personally, I think had Bret stayed then Owen would have been a one time WWF champion by May 99 and retired, living as the firefighter he planned to be... perhaps Final Destination style luck sees him killed fighting a fire instead?
SO realistically... it goes like this if Montreal doesn't happen and Bret is staying.
Bret doesn't drop to Shawn at Survivor Series... he chooses to drop to Taker. Shawn gets pissed and leaves for WCW... dying less than a year later in a drug related incident or car accident.
Bret gets the belt back at the Rumble to drop to Austin at 14 - but makes sure there is an "out" for himself via Taker interference, rather than letting Austin get the straight revenge and win for the prior year. That devalues Austin as there was no Mike Tyson/McMahon feud to kick off his run.
The Rock gets held down in the IC division at least another year, and Bret refuses to help elevate him as he feels he hasn't "paid his dues yet". This annoys Vince and the Ano'i/Samoan faction and starts to cause issues between them and the Harts. The Samoans feel Bret owes for Yoko doing him the favor back as Yoko could have legit refused to do so.
Davey Boy is made to put Rock over instead and buried in the match, souring relations further. We see a Hart Family v Samoan feud with Haku coming back to the WWE and legit making clear to Bret that no more of his games will be tolerated.
Bret finally refuses to job to Rocky one last time and it causes a severe altercation backstage with Haku, Afa and other members of the Anoi' family. Rocky stays out of it wisely but it's the final straw for Vince who makes plans for life without Bret.
Screwjob situation occurs at Wrestlemania 15 when Rocky is handed a shock and "screwjob" title win. Bret is without a WCW contract and has to accept reduced terms, but the bad blood with the Samoan/Tongans is even there in WCW with guys like The Barbarian there.
Owen retires rather than face repercussions (although the Samoans never have an issue with him or Davey, only Bret, Bruce and Neidhart who all stick close to Bret) and the Hart family "splinters" in real life. with Davey staying in the WWF and being pushed - with Rocky dropping the title to him as a receipt for putting him over strong at one of their UK Events... Davey gets to lift the title in the UK and top off his career... he never goes to WCW and gets the back injury... away from Neidhart's influence he cleans himself up and becomes a solid WWE main eventer for the later years of his life, helping the burgeoning UK PPV/RAW events and their TV deal with Channel 4 and later ITV although as with real life - a lot of the damage was done already.
The controversy helps make the WWF must see again and with Rock and Austin's "Battle Of THe Badasses" it goes over the top... it takes another year to win the war but it's still won... Foley doesn't get the title but Davey does.
Bret makes it to Mania 15 tops... made REAL enemies that severely limit his options in the business and Shawn is dead...with Davey perhaps still being here, although badly aging. Butterfly Effect perhaps... but VERY likely had he not gone when he did.
If his options were very limited Hart could've went to ECW for a year or two to refresh his image and then try to return to WWE.
I think it's completely baseless to say Bret would've refused to lose to someone else.....huh? I mean, where does that come from? Bret was a 5 time champion.....meaning he lost it 5 times. One was the screwjob, but he never had a problem putting anyone else over. That was an extraordinary situation. At least Bret was up front about it and didn't fake an injury like Shawn. Seems you guys who go hard at Bret always forget that part. Shawn hurt the product way more than Bret, with all his BS around that time period.
Suggesting Bret would've blocked Rock or Jericho's push is flat out ridiculous and baseless. Bret made Owen a star, made Austin legit, put Shawn over in the first place, put Yokozuna over, etc.
Edit: whoa! I made my post after reading halfway through your message. If I knew just how ridiculous the post would get, I wouldn't have bothered replying. Wow.