There was once a rumor in which Randy Savage was set to go back to the WWF in late 1996 once his initial WCW contract signed from the end of 1994 was set to expire. That's why the bookers had Savage (a Team WCW face) constantly get beaten down by the nWo, whether it'd be Hollywood Hogan, Scott Hall, Kevin Nash and The Giant up until Halloween Havoc '96.
That's when WCW had Roddy Piper as their backup plan in case Randy Savage decided to rejoin the WWF, given that Vince McMahon's New Generation Era had failed with Bret Hart, Kevin Nash and Shawn Michaels as their top draws, plus Savage would've developed a proven track record as the WWF's top draw on his resume.
Also, Bret was supposed to be going to WCW because they were gonna give the Hogan role in the nWo to Bret if he joined them. But once Bret eventually reupped with the WWF by Survivor Series '96, he had an epic feud with Steve Austin, Shawn Michaels and The Undertaker,...until his 20 year contract became an issue, when Vince realized that the WWF was losing money because he was spending more money on Bret than Bret was drawing butts in the seats, largely because Bret's a total boring hack and he's not a megastar on the level of Hogan, Savage, Austin and Rock.
WWF was legitimately in near financial peril at the time, because then Vince would've had Austin, Undertaker and Michaels demanding the exact same contract as Bret, so the easy way for the WWF would be to deliberately breach Bret's 20 year contract and convince the guy to revisit talks with WCW as 1997 was almost coming to a close, plus Bret just turned 40 years old, while Shawn (even though he's only 32) still had plenty of good years left in the tank with the proper booking, so it was easier for Vince to go with the younger model than the aging veteran who is to be put out to pasture by Survivor Series '97 in Montreal.
Face it, 1996 was also the year when Bret was physically past his prime and his body was starting to break down as being active non-stop for virtually his whole wrestling career took its toll on especially his knees. He would eventually miss only three weeks for knee surgery in 1997 after IYH:Revenge of the Taker, but how long can Bret physically hold up if he can't be at the same physical peak level he was from 1984-1995?