This presentation examines the attitudes of three presidents toward American press and media: John F. Kennedy, Richard Nixon and Donald Trump. More specifically, the American Presidency Project Archival database was used to gather the instances in which these three presidents used the term “press” and “media” in news conferences, interviews and miscellaneous remarks. These mentionings were gathered to gauge the attitude these presidents had towards these democratic entities. With context, each time Kennedy, Nixon and Trump used the terms “press” and “media” could be broken into different categories involving tone and compared/contrasted as such. Press freedom in this country is crucial to ensure a sustained and thriving democracy. Thus, any condemnation of the press by political elites could pose a threat to such democratic ideals.