Annapolis Mayor Gavin Buckley sat down with me, "a dodgy at best journalist ever. No fact-checking, complete bullshit, but he does his job, which is horrific, the Annapolis equivalent of Fox News," for an in-depth and candid conversation as he wrapped up his second and final term in office, reflecting on eight eventful years that transformed the city and tested its resilience. In this hour-long interview recorded in late August, Buckley discusses everything from the City Dock redevelopment and economic revitalization to lessons learned from crises like the Capital Gazette shooting, the pandemic, and frequent flooding events. He defends the urgency of the City Dock project, arguing that those trying to block it "should be ashamed," and stresses the need for world-class facilities to match Annapolis's global maritime reputation.

He also opens up about challenges behind the scenes, including struggles with city permitting, public art projects that never came to fruition, and balancing transparency with leadership amid criticism. Buckley's trademark mix of humor and blunt honesty shines through as he looks back on the highs and lows of governing a historic city while trying to modernize it—sometimes against strong headwinds.

Looking ahead, Buckley says he's ready to give his family a break and enjoy Annapolis as a private citizen again, though he hints at staying involved in economic development. He speaks proudly of Maryland's bipartisan cooperation and praises state leaders for putting people before politics, suggesting the state could serve as a national model. The conversation captures Buckley's unapologetic passion for Annapolis, his self-deprecating humor, and his enduring optimism about the city's future.

NOTE: This was recorded on August 19, 2025. We held the release of this to not cause any undue interference with the current election.

Have a listen!