In the American press, news publishers and advertisers have enjoyed a close relationship well before the birth of our nation. When Benjamin Franklin bought The Pennsylvania Gazette in 1729, he became the owner of a communications platform and printed both information and advertisements. Today, news publishers and tech companies like Facebook and Twitter do the same—they publish and distribute news and commercial messages. Organizations like The New York Times and Washington Post produce more than news stories. News outlets have new departments—branded content studios, product marketing teams, and innovation teams—that are dedicated to creating and placing marketing messages beneath our gaze as we turn the physical page of a paper or scroll, click, and tap our screens throughout the day. This dissertation examines how advertisers aim to invisibly inject their messages into and alongside news stories by investigating the relationship between the business and newsroom side of various news publications. The research methodology is qualitative and draws upon over 125 interviews with people who work at news organizations, ad agencies, media and tech companies. This dissertation has a simple premise: compare the words of CEOs, executive leadership, and mission statements with the actions of news organizations to identify where discrepancies exist between the core tenets of journalism and its practice.