Fun discussion on this week's "Center Stage Chronicles" pod about how Macho Man's deal with the WWF was set to expire around WM5 (which seems like a big oversight by the WWF).
It could have been Savage confronting Flair at Wrestle War instead. OR Savage showing up after Wrestle War and attacking Steamboat.
With Bossman making 20K a night vs Hogan in Feb. it would have been INSANE for Macho to decide to jump to WCW, money guarantee or not.
Hogan's deal was up around this time too and some preliminary talks did happen if I remember the WONs correctly, but I'm sure it was just Hogan getting his leverage secured. Piper was talking to WCW in early 89 as well. IIRC he even had dinner with Jim Crockett, who was still an office geek after his family sold the company. He and Piper were friendly though.
Hogan had flirted with WGN in 1987ish to sign a deal with them, and then WGN would air AWA and Hogan would be the top draw. How far that got along as a bargaining chip vs reality is fairly obvious. You would think there could have been a plan B where WGN would at least help fund the AWA signing Sgt Slaughter and other free agents and try to test the ratings waters. AWA did good numbers on ESPN despite ESPN airing them all over the place.