The collapse of Hong Kong’s last big pro-democracy news outlet, Stand News, caps one of the world’s most dramatic declines in press freedom this year.

From the closure of Jimmy Lai’s Apple Daily newspaper in July to the raid, arrests and asset seizures that precipitated Stand News’s shuttering Wednesday, the global financial hub has gone from being one of Asia’s most free-wheeling media markets to one of its most regulated.

In addition to employing a national security law that carries sentences as long as life in prison, Hong Kong authorities have begun charging journalists and internet users under a colonial-era sedition law that can jail a writer for up to two years.

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