This Article explains why the legal case for the recently disclosed National Security Agency surveillance program turns out to be stronger than what the Administration has advanced. In defending its action, the Administration overlooked the details surrounding one of the most important periods of presidentially imposed surveillance in wartime--President Franklin Delano Roosevelt's (FDR) wiretapping and his secret end-run around both the wiretapping prohibition enacted by Congress and decisions of the United States Supreme Court. In our view, the argument does not quite carry the day, but it is a much heftier one than those that the Administration has put forth to date to justify its NSA program. The secret history, moreover, serves as a powerful new backdrop against which to view today's controversy.