It has turned out to be the case. Selling the combination of good content and good editorial through the internet is a successful business model. It just isn't a broadly successful business model. It only works for a few prestigious brands. Charging for print content worked for a lot more smaller and more obscure outfits like local news organizations, but on the internet, everyone competes with everyone, and those outfits can't compete with the big names. I personally think that's a bummer, but it doesn't mean that pay-for-content-and-editorial is a dead business model, it has just changed to the kind of model where a few well-known companies accumulate all the benefit.
Of course there are other successful business models too, which you and your parent have mentioned a couple of:
You can sell ads against "10000000 random sources of free news". Lots of people are doing this, but most of the profit accrues to the big advertising sellers rather than the content creators, but still, it does work. I would personally rather be one of the companies with enough clout to go the pay-for-content-and-editorial route.
There is also direct-to-customer, like lots of people do with Patreon or some people do by running their own subscription services (like Stratechery or Sam Harris). This seems like a really good model to me, but I think it's still pretty nascent and hard to make money with.
But what I've been saying in this thread is: what model is Medium going for? They have a pay-wall, so it isn't the second model (free news), but they don't seem to be doing editorial so I don't think it's the first model, and they also don't seem to be aiming at their creators building a person-to-person following, so it doesn't seem like the third model either.
I'm just not sure where they fit in, is all I'm saying.
To add to this, this was the misguided idea that news people had, thinking it would allow them to survey.
That "Sure, we might now have 10000000 sources of free content, but because of that people will value our curation that separates the wheat from the chuff more, and pay us for that" (or, in a variation of this, our "professionalism" and "knowledgable meta-analysis of news").
Turned out not to be the case. 90% of the people are totally fine with those 10000000 random sources of free news, thank you very much.