Business Buckley came to Maryland in 1992 by boat, with only 200 dollars in cash; in the region, he found work as a waiter and farm laborer, among other jobs. He was one of several partners in West Village LLC, which renovated a strip of dilapidated buildings on West Street near Tsunami in 2001 and restored a variety of businesses to what had become a "relatively desolate" part of the city. Buckley's businesses accrued several debts and contract disputes between 2006 and 2012, which he attributed to cash flow problems due to the
Great Recession. Buckley was also cited by local authorities for failing to display boat registration numbers and failing to obtain a rental license. Throughout the controversy, Buckley argued that Annapolis's economic development depended on loosening historic preservation policies, saying "We have to celebrate our history, but you can't get stuck in it." In the general election campaign, Buckley proposed a "firestorm" of reform proposals, including replacing curbside parking on busy Main Street with a trolley, that his Republican opponent, incumbent mayor
Mike Pantelides, mostly dismissed as unrealistic. The race was unusual for its relative civility, with Buckley and Pantelides dining together publicly. Pantelides's campaign at times contrasted his Annapolis pedigree with Buckley's Australian identity, but Buckley believes this tactic backfired, telling an Australian newspaper "People are very nice to Australians here." As Annapolis Mayor, Buckley convened the City Dock Action Committee Buckley has worked to strengthen ties with both of the city's two colleges: St. John's College and the United States Naval Academy. Work with the Naval Academy has included the development of a comprehensive flood mitigation plan that addresses the combined effects of land subsidence, sea level rise, coastal flooding/storm surge and stormwater management. Coordinating the Academy's plans with the City Dock Action Committee's work has fostered more consistent coordination on resiliency issues, with USNA leadership serving on the City Dock Action Committee and City personnel as members of the Academy's Sea Level Rise Advisory Council. His administration has undertaken numerous infrastructure projects, including HUD's Choice Neighborhood Initiative (CNI), a partnership with the Housing Authority of the City of Annapolis to revitalize distressed public housing properties at Eastport Terrace and Harbour House. Trump's press secretary,
Sarah Huckabee Sanders, called Buckley later that day; on the following day, the White House issued the requested proclamation, saying Trump had ordered it as soon as he learned of Buckley's petition. In the wake of the shooting, Buckley called for stronger gun control, blaming the
National Rifle Association of America for opposing legislation restricting gun sales to certain people with mental illnesses, such as the accused Capital Gazette shooter, and suggested looking into gun buyback programs such as
those enacted in Australia. He remained in office until December 1, 2025. On February 11, 2026, Buckley registered as a candidate for the Anne Arundel County Council. ==Personal life==