Kaplan's New York Observer played a pivotal role in training a new wave of media reporters, shaping their understanding of journalism as it grew increasingly self-aware and focused on its own processes. This publication became an essential institution within the New York media landscape, influencing how stories were told and reported. The rise of this self-conscious journalism coincided with the media's evolving relationship with significant figures like Donald Trump, who became emblematic of the challenges journalists faced.

Trump's presence in the news cycle was a source of discomfort for media professionals in New York. Writing about him brought about a feeling of shame, as many believed it compromised journalistic integrity. Choosing not to cover Trump, or critically analyzing his role in the media, was seen as a moral stance against the sensationalism that surrounded his public persona. This dynamic reflected broader tensions in journalism as it navigated the complexities of reporting on such a polarizing figure while maintaining credibility.