Looking back at Andre's career, at what point do you think it would have been best for the big guy to hang up his size 24's?
– Right after his Wrestlemania 1 match? It would have made the inaugural Wrestlemania more special and would leave us with the enduring memory of the smiling Giant throwing money out to the crowd before saying goodbye.
– Following the loss to Hogan at Wrestlemania III? He could shake Hogan's hand and say, “You're the better man” or become an evil manager who wears custom suits and knocks over camera guys. (He was actually pretty good in that role.)
– Following Summerslam 88? This was his last main event match, and I thought it was sad to see him moved down the card to wrestle Jake Roberts and The Ultimate Warrior when he was really in no condition to work anymore. Perhaps he could have been taken off TV and used as a house show attraction. But really, was there any point in having him go on after Summerslam other than that he didn't want to give it up and Vince wanted to milk the Giant for every dollar he could get out of him?
– Or would you go with some other scenario I didn't bring up?
I think Wrestlemania 3 was the right time to go out in hindsight. Take the leg drop, beat up Heenan and call it a day.