This article describes a lesson in which students will examine several views expressed by the founders to understand the context for including freedom of the press in the First Amendment. Students will be asked to think about the role that the news media and the need to be an informed citizen continue to play in our democracy. Students will examine a recent court case and excerpts from the court ruling as they build practical skills in evaluating information and form their own opinion on who qualifies as a journalist in the twenty-first century. Students will then complete a written assignment in which they construct an argument relating to press freedom. The guiding questions of the lesson are: (1) What is freedom of the press in the 21st century? (2) Why was it established? (3) What is its significance in a constitutional democracy? (4) Who does it apply to? This lesson enables students to examine the issue of freedom of the press both as it was conceived by the founders and as it appears in the twenty first century, when the Internet has transformed communications between people.