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For the longest of time, I always thought Bret's contract expired at the end of the night (midnight). Therefore, he would technically not be obligated to attend the show the following day. However, in recent years it's been made known that Bret's contract actually expired almost a month later. In that case, he legit could have done anything on Raw and was still under contract. This is where the murky water is hard to tread through:
Was there an agreement made between Vince & Bret that the Montreal match no matter what would be his final appearance with the company before the idea of Bret dropping to Shawn became pitched? This would be a great question to get an answer to.
Bret has stated that he fulfilled all his required dates in the contract and didn't have to show up anywhere after & including that match. I wonder if Vince's big hang up was not the Bret/Shawn issue, but more of the Bret/Vince/Eric issue. I have a feeling that even if Bret said that he would do ANYTHING with the belt on Raw that Vince asked, Vince did not trust that Eric didn't shelve him 100 million or something to ditch Raw and go to Nitro instead. This would be a logical reason because Bret fulfilled his WWF responsibilities of his contract already there for it would be like a CM Punk walk out, minus the no-compete clause that didn't exist back then.
For the record, I do not think Bret would have shown up on Nitro with the belt if Vince agreed to let Bret retain at SS and drop it the following night. I truly believe Bret in that he felt shafted by Shawn as a friend & colleague at the time and that is the only reason why he refused to do the job at SS.
Anything, even tar & feathering Bret's character in the ring, the following night on Raw would have been better than what actually happened at SS.
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