First time, long time. As I was reading the Observer Flashback, I was reminded of a question that I probably already know the answer to (Vince gonna Vince). What was the logic behind pairing decidedly-less-cool-since-he-went-babyface Shawn with who, at the time, I thought was his Mexican grandfather?
Combination of stuff. Mostly, as noted, Vince not really understanding what people wanted to see out of Shawn Michaels.