The plan for WM16 from May 1999 was always Rock/Austin 2 at WM in a mega babyface vs mega babyface match, Rock as the Rumble winner, Austin as the WWF champion, Rock getting his win back. There was also a big talk to turn Austin heel in October 99 because Rock was so hot but Austin was out for the neck surgery the next month. Austin/HHH was never the plan at any point for WM16, they already wrestled plenty of times on RAW in 99 and had a PPV match in October.
Very interesting. I'm curious how the heel turn would have gone in 1999, with Taker and Triple H both great heels at the time. Just the whole late 1999 - 2000 scenario with a healthy Austin and Taker sounds incredible. There's no doubt that The Rock would have been huge. But where does that leave Triple H, say an Austin heel turn happened?
2000 was already an awesome main event scene, but it could have been "fuckin" incredible with the addition of the other two. As long as Taker was still in his Ministry stage.