Shawn had spent five years cultivating that womanizing, sexy boy gimmick and I think it was to portray Shawn in a different light. We all know Shawn wasn't happy with it but Vince wanted to push the "Boyhood Dream" angle.

I do think Vince was legitimately concerned about Shawn's off-screen behavior if not out right worried. The LAST thing he needed was the WWF Champion and FACE of the WWF overdosing on drugs or even getting jumped (like in Syracuse, NY) Vince knew that Triple H couldn't keep Shawn in check so he brought in Lothario and even put him with Tim White.

Vince knew Shawn was an insecure womanizer plagued with drug addiction issues. I think Vince HOPED the break-up of the Kliq and the responsibility of being WWF Champion would put Michaels on the straight and narrow. Vince knew who the bad seeds were (Scott Hall, Sean Waltman) and who the good ones were (Triple H, Kevin Nash) and tried HARD to keep Nash who had SOME level of influence on HBK but once Nash jumped there was no one to rein in HBK on the road.

Then the NWO hit and the WCW was beating the WWF in the ratings wars. Shawn started to crack under the pressure and people were LOVING it!

I also love the fact that none of Shawn's stories matches up with what other people say about him including his own friends.

Shawn was pretty much alone at this point. His friends were gone. HHH was being buried. His "relationship" with Sunny had ended, he was failing as champion.....the writing was pretty much on the wall. Vince needed somebody to watch over him or it would be OD city.