a rental license. A dispute with the local Historic Preservation Committee in 2015 over a large mural on the outside of Buckley's Tsunami restaurant brought him to public attention in municipal politics. 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." Politics Buckley ran for mayor of Annapolis in 2017 with no prior political experience. He defeated longtime Annapolis State Senator John Astle in a Democratic primary with unusually high turnout, a "stunning" result after a primary campaign in which he presented himself as a contributor to the renewal of downtown Annapolis, a fresh voice from outside the political system, and an ally of underprivileged Annapolitans. 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." Buckley defeated Pantelides by over 1,000 votes in the November election. In office, Buckley fought to relax zoning restrictions in Annapolis's City Dock area to match those in the West Street area where his restaurants operated, a move he argued was necessary to revitalize economic activity in "the best real estate that the city has". He introduced legislation to do so in a City Council meeting in May 2018, where it was rejected after historic preservationist opponents raised concerns about losing the area's designation as a National Historic Landmark District and pointed out that a "cultural landscape study" mandated by the city's master plan for the area was still underway. Buckley announced his intention to reintroduce the legislation with more sponsors after the study had been completed, and in June the National Trust for Historic Preservation named the district one of "America's Most Endangered Historic Places." Buckley was in office during the Capital Gazette shooting on 28 June 2018, in which five people were killed at a local newspaper's office. In the aftermath, Buckley requested a federal proclamation allowing flags to be flown at half-mast; he told the press on 2 July that the administration