"Electable" is a code word for "can carry the ball past the media's goal-line stand". And if the media-ocres are saying that people are going to Trump because of wanting to side with the "winner", well, there ya go. That means, in their minds, he's already got past them. In no other case would they allow the word "winner" to appear in such a context.
You're absolutely right, though the Media, as corrupt and depraved as it is, is not the only obstacle, and Trump has proven that he can dispatch the Media-ogres along with the rest of the tangles of the Gordian Knot (note tagline).
Many people did not believe that Trump could get past the Media et al.--establishment Republicans, Democrat politicians, maybe some other things--but when he showed that he can, they jumped to his support--not because they want to be on a winner's bandwagon, but because they wanted to support him all along and now see a path to victory.
Part of the Trump magic is that he is not a politician. Part is that he's honest--blurts out what he thinks and let the chips fall where they may. Part is his obvious love for America. And part is his indomitability.
All of this is part of why I support him enthusiastically, and another, very important part of it is that he promises to halt the decadence of Western Civilization in America and restore ascendancy.
Furthermore, if he succeeds, he may inspire the rest of Western Civilization to do the same.