I believe its this notion that liberal Hollywood looks after each other.

Absolutely they do. When Bruce Jenner first started transitioning, but hadn't formally announced it, all of Hollywood and the tabloids started speculating if he was in fact going through this change... All based off his appearance after a surgery left his throat looking like it had no more Adam's apple. .. Shortly after that the broads on the daytime show The Talk had it as a topic of speculation on the show, saying things like "it seems he could be transitioning or beginning the journey to..." and "if he is he should just let the world know because everyone will be behind him" , "there's nothing wrong with it, he shouldn't be afraid to show his true colours, well support and love him/her".

It was like all of them already knew. Bruce's publicist most likely called all the necessary people to tell them ahead of time, and it was implimented through out Hollywood and the tabloids to start the whole speculation process, the whole support stance, etc. to help soften the blow for when he finally came out with it himself. .. if you plant an idea subtly in people's heads like that before it actually comes to light, people won't be as shocked because they'll think "yeah I already had a feeling that's what he was doing", or, "yeah it was obvious that's what was going on". Then it's easier for the person in question to gain the support they need and normalize something that would otherwise be super big and surprising news that would be talked about forever.