In the short-term, languages with good developer outreach and other factors win. But you don't get things like generics or the .NET TPL without some serious long-term vision. I really do believe well-designed languages win over a long enough timescale.
Even popularity is a value, as it automatically provides a community, but it's also a pitfall, as massive popularity inevitably means the average programmer of language X becomes as smart, careful and reliable as the average programmer irrespective of language. And, to put it mildly, that's not a positive evolution. That, above all others, was VB and Delphi's downfall.
On three axes, I would argue VB, Javascript and Delphi did/do incredibly well: ease of development (of small-ish programs), and the deployment story, as well as the empowerment they provided.
On things like consistency, developer productivity, batteries included (Delphi was better on the batteries included front), type system soundness, ... they were somewhat sub-par.
It's just what people value at the time. And of course, it is critical during a career in development to distinguish yourself from the average programmer.