Shepherd was appointed vice-chair of the city's five-man Board of Public Works. The most powerful public entity in the District of Columbia, the Board of Public Works was actually an independent entity from the territorial government, reporting directly to Congress, but kept within the territory's sphere of influence by making the governor its chairman. Cooke, however, rarely attended the Board's meetings (probably at Shepherd's urging), allowing Vice-Chair Shepherd to preside. He asserted himself as a leader to such an extent that he often did not bother to consult the other members of the Board before he made decisions and took sweeping action. His abilities as a political operator, according to D.C. journalist Sam Smith, were formidable: