This Article honors Monroe Freedman’s iconic piece on the hardest questions for a criminal defense attorney by posing the same question for prosecutors. What is the hardest question for a prosecutor? Even this is a hard question. The thousands of federal, state, and local prosecutors in the country would give widely varying responses—discretionary charging, immunity grants, bargained pleas, unreliable witnesses, police testimony, and disclosure duties, for starters. Too, prosecutors are not a generic group. Just as some defense lawyers might recoil or be indifferent to Freedman’s provocative thesis, so might many prosecutors reject or be indifferent to what this Article proposes is the hardest question for them.