The existential crisis that Jay referred to was a long time in the making, but when it happened, it happened fast. Someone (not me) could write a very long book on this topic, but let me do the CliffsNotes version. First, the Internet allowed people to get information without paying for it, which was not good for the newspaper business, which sold ads based on the number of subscribers. Second, the Internet and the smartphone made it so people could get information whenever they wanted it, wherever they wanted it, which was not good for the television industry, which sold ads based on the number of people who sat down to watch TV at an appointed time. Third, the 2008 financial crisis crushed the very businesses that bought the ads that funded the media industry. Newspapers were laying off people or closing altogether. The more experienced reporters were being offered buyouts, so outlets could replace them with cheaper, younger reporters. You now had fewer reporters with less experience and fewer editors writing more often to meet the never-ending deadline of the Internet.

Fourth, while media was weakened by technology and economics, it was also losing its sacred place in our democracy in the eyes of many Americans. By the time Obama had started running for president, the halcyon days of journalism were a distant memory. Public trust in the media declined precipitously, and by the time Trump won the 2016 election, the media was about as popular as Trump himself. Some of this decline can be attributed to a rise in skepticism of American institutions, but the media is not blameless either. Several high-profile incidents have given the public legitimate reasons to be more skeptical. Foremost among these is the coverage of the run-up to the Iraq war, where the media—and The New York Times, in particular—parroted the Bush administration’s false claims about the presence of weapons of mass destruction in Iraq.

Finally, the Republican Party and the right-wing media had been running a decades-long effort to convince their voters that the media was their enemy and to create an alternative version of reality. Fox News, the Republican propaganda outlet, which marketed itself under the banner of being “fair and balanced,” was the embodiment of the effort to nullify news that ran counter to the political wishes of the Republican Party and conservative activists.

All of this meant that Obama was entering office at a time when it was harder than ever to reach people through the news media, and people were more skeptical than ever before about anything they learned from the media. Not exactly a recipe for success for a new president (and his communications director) trying to tell the country about his agenda.