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I’ve chosen to honor Monroe Freedman’s iconic essay on the hardest questions for a criminal defense attorney by posing the same question for prosecutors. What is the hardest question for a prosecutor? This in itself is a hard question. The thousands of federal, state, and local prosecutors in the country would likely 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 I propose is the hardest question for them.

For prosecutors, the hardest question they face is whether the person they are prosecuting is actually innocent. Nobody except the accused really knows the answer to that question, certainly not the prosecutor, however strongly he may believe in the defendant’s guilt and the credibility of the proof.