About
Jason Gutterman, the operator of Amagansett Press, has built a YouTube channel with nearly 600,000 subscribers and 167 million views on a specific, repeatable formula: film in public spaces, provoke confrontations with authorities or citizens, and monetize the resulting conflict. Flanked by his son Ben Gutterman (sister channel "Watching The Watchmen"), this father-son duo produces "First Amendment audits" — traveling over 200,000 miles across the US documenting encounters that blur the line between civil rights activism and targeted provocation.
Amagansett Press: From Alec Baldwin Letter Wars to National First Amendment Auditing
The channel was established on January 14, 2009. Its roots trace to Amagansett, a hamlet in East Hampton, Long Island. In 2013, a Jason Gutterman engaged in a high-profile exchange of letters in The East Hampton Star with actor Alec Baldwin — revealing an appetite for public confrontation before his auditing career began. From these local disputes, the operation evolved into full-time, national content creation. By 2024: 475 videos and 167M+ views.
Amagansett Press Content: Confrontational Public Filming and Police Encounters
The format is consistent: arrive at a public building (post office, police station, government office), film from public areas, and document the reactions of employees and officers. Encounters escalate when authorities challenge the filming. The resulting confrontations — ranging from civil to heated — are the content. Titles are optimized for outrage and engagement. The stated justification is First Amendment advocacy; critics characterize it as deliberate provocation for profit.
How Amagansett Press Makes Money
Revenue comes from YouTube AdSense on high-engagement confrontation content, direct viewer donations, and community support through YouTube memberships. The confrontational format generates high click-through rates and extended watch times, making it algorithmically effective.
Amagansett Press: Controversies and Legal Encounters
The channel's entire premise generates controversy. Gutterman has been involved in multiple encounters with law enforcement, some resulting in detention or arrest. His supporters view these as proof of government overreach; critics see them as manufactured confrontations. The father-son operation has drawn criticism from both law enforcement advocates and free speech purists who question whether deliberately provoking encounters constitutes genuine activism.
Amagansett Press Today
With 600K subscribers built on confrontation content, Amagansett Press demonstrates the commercial viability of the First Amendment audit genre. Whether the operation represents genuine civil rights activism or calculated provocation for profit remains the central, unresolved question of its brand.