Winston Churchill’s description of Stalinist Russia in 1939 – he called it a riddle, wrapped in a mystery, inside an enigma – easily could have been said about the case of Jonathan Jay Pollard, the U.S. Naval Intelligence analyst who, in March of 1987, received a mystifying life sentence for passing classified secrets to an American ally; Israel. Now, twenty five years later, the debate over America’s most controversial spy has apparently once again been rekindled. This is an attempt to shed a bright light over a dark stain on both the American judicial system and our intelligence community, while, at the same time, solve a decades old puzzle – knowing that, for way too long, the truth surrounding the most gut wrenching spy cases has remained hidden, blurred and obscured.