Hey Scott, watching Darkside of the ring and there are some aspects that make me feel it was a work. Scott Hall made some great points regarding the cameramen hitting the angles, spitting on Vince, and making the WCW sign, and I never understood why Bret would let Shawn put him in his finisher. I truly believe Vince, Shawn, and Bret worked everyone. 

Bret let Shawn do the Sharpshooter because there’s no way to screw someone over unless the referee and timekeeper are both in on the deal.  Normally the way you do a shoot finish is like Moolah and Richter or Sting and Jeff Hardy, where you get someone in a pin fall situation and then don’t let them kick out.  That’s what Bret was training against.  Montreal was wholly unique  and needed a lot of moving parts to pull off.