With all due respect, putting up a “pay wall” is exactly what these organizations don’t need. They need to decentralize, get further out into the world, not hole-up behind a wall and try to tough it out.
What worked for HBO won’t work for the news because HBO is fiction, and news is not. You can take years writing and developing a story on HBO, polish it, cut out parts that don’t support the plot you’ve devised, even drop the series in the middle if you lose interest. That doesn’t happen with the news. News is happening all the time, on its own schedule, all over the place, including many places you don’t have reporters.
I’m working on my own response to Simon’s argument, but I think Winer is correct that the HBO model is fundamentally incompatible with the nature of news.