October 30, 2025
Chatting the Pictures

Chatting The Pictures: Trump Raising the Roof

Welcome to Chatting the Pictures. Every two weeks, we present a short, lively video discussion between Michael Shaw, publisher of Reading the Pictures, and writer, professor, and historian, Cara Finnegan, examining a significant picture in the news. Chatting the Pictures is produced by Liliana Michelena.

By Staff
About the Video

White House staffer Molly Riley captured President Trump conducting a rooftop inspection with a private architect on August 5, 2025, as he surveyed plans for his $200 million ballroom project. The 90,000-square-foot, 650-person banquet hall would replace the entire East Wing and nearly double the building’s footprint in the most intensive White House renovation since the 1950s. Trump promises the project will be privately funded. In the photo, Trump is positioned above the Press Briefing Room, with reporters assembled below, shouting questions back and forth about his plans. The walkabout included a stop above the Oval Office area, where Trump surveyed the recently paved-over Rose Garden.

The conversation highlights how Trump’s rooftop stance turns the White House into his personal stage, using height and body language to send a not-so-subtle message of dominance over the assembled press and the national narrative itself. His showy, hands-on presence blurs the line between leader and developer, raising bigger questions about power, public trust, and just how far private ambition can reach in America’s most symbolic space.

You can find all the Chatting the Pictures replays here.

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Panelists

Michael Shaw

An analyst of news photos and visual journalism, and a frequent lecturer and writer on visual politics, photojournalism and media literacy, Michael is the founder and publisher of Reading the Pictures.

Cara Finnegan

Cara Finnegan is a writer, photo historian, and professor of Communication at the University of Illinois. She has been affiliated with Reading The Pictures for nearly 15 years, most recently as co-host of Chatting The Pictures. Her most recent book is Photographic Presidents: Making History from Daguerreotype to Digital.

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