Brian Beutler makes a very good point about the current crop of Democratic advisors:
Yes, media has changed in the ensuing years, but so too have Democrats. They have lost all confidence in their ability to persuade the masses of anything. In their despondency, they have devalued what is true and stopped even articulating what they want the public to believe. They have replaced storytelling rooted in facts with a defeatist sense that public sentiment is fixed, and that they must conform to it.
It’s so frustrating to see that too many Democrats just don’t think they can change people’s minds. It’s made all the harder by a media environment that is unfriendly (to say the least) to Democrats. On that latter topic, there are two things that professional Democrats need to do.
First, they need to learn how to cede some power. There are a whole bunch of Democrats who are willing to spread Democratic messages–and messages somewhat aligned with Democrats (these aren’t the same thing–for free. But the unwillingness of most Democrats to truly engage rank-and-file supporters (as opposed to bombarding them with emails shrieking about THE CRISIS and then asking for a donation) just alienates them. Essentially, they need to decide if they are willing to cede some of the agenda to other people, or if the Iron Law of Institutions will prevail.
Second, they need to figure out a way to buy media outlets. Probably not explicitly, but donors would be far better off if there were way to take over media outlets in swing states, both print and television. At the very least, just not having rightwingers running and owning them would be an improvement. And the money is there: as a thought experiment, imagine if there were a twenty percent tax on donations that went to a media acquisition fund. I would argue that roughly $500 million spent this way is vastly superior to buying ads from media outlets that, too often, are biased against Democrats.
It wouldn’t need to be Fox News either: just the occasional op-ed and coverage biased in a way that’s more friendly–or at least, less antagonistic–to Democrats.
But these strategies both require that you believe you can change people’s minds, and the Democratic establishment seems to have given up on that.

Republicans are VERY good at this. I was talking to one of the less intelligent political staffers for one of my senators who explained to me (when I was correcting him about something incorrect his office was saying about the ACA during the last administration) that if people said something enough, it became true. “If you call a chair a table enough it becomes a table.” I’m pretty sure that was him not understanding the instructions to propagandize when people called. I felt very shaken after.
I assume the defeatist democrats are getting paid (or blackmailed) by the same rich people that are paying the successful republicans. I mean, maybe never attribute anything to malice that could be explained by stupidity, but also… there’s a lot of payment and blackmail going on these days.
Nobody cared about trans folks 10 years ago. Heck, people were cool with Caitlyn Jenner. Propaganda has turned them into a wedge.