Deputy U.S. Solicitor General Michael Dreeben argued his 100th case on Wednesday, and it may have been his toughest—in part because of the wild array of hypotheticals the justices threw at him and his adversary.

Dreeben was defending the 2014 prosecution of former Virginia Gov. Robert McDonnell for taking gifts and money from Virginia businessman Johnnie Williams in exchange for what the government said were “official acts.” Those acts included arranging meetings and attending events that could benefit Williams’ diet-supplement company.

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