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In 1952, when he was in his sophomore year at Harvard, Bailey became bored with academe and joined the Navy. He just missed the Korean War, but found two permanent passions: flying and the law, which he considers integrally related. "If I ran a school for criminal lawyers," he wrote in his 1971 book The Defense Never Rests, "I would teach them all to fly. I would send them up when the weather was rough, when the planes were in tough shape, when the birds were walking. The ones who survived would understand the meaning of 'alone.' " Bailey had transferred to the Marines to do his jet flight duty, and wound up, by a felicitous military fluke, as his squadron's chief legal officer. He spent the last 17 months of his Marine hitch prosecuting, defending, judging or investigating military cases. On the side, he apprenticed with a civilian lawyer, a fact that helped him to talk his way into Boston University Law School after his discharge, even though he had not finished college.
Bailey graduated first in his class, despite spending much of his time watching actual trials and running a successful investigative firm servicing local lawyers. During classes he often read in apparent boredom; when his professors tried to tag him with sudden questions, he would smugly answer in minute detail, then go back to his reading. His worst grade, ironically, was on a criminal law exam—but only because he is plagued with a bad case of lefthanders' handwriting and could not finish all his answers. After that debacle, he was permitted to bring a typewriter to all his exams; even today he writes only his signature and types everything else.
Bailey's only worry about entering criminal law was that there would not be much money in it, and he did not strike it rich immediately. But he did the next best thing: he became almost instantly famous.
When he got his law degree in 1960, the headlines in Massachusetts were filled with the case of George Edgerly, a Lowell auto mechanic accused of murdering his wife and then chopping up her body. By mistake, Edgerly's ailing defense attorney had agreed to the admission of a polygraph test that an expert claimed proved Edgerly's guilt. The lawyer desperately looked around for anyone who knew enough about relatively new techniques to cross-examine the supposed expert. Bailey happened to be studying polygraphs for another client's defense. Barely three months after his admission to the bar, he got what he called "a slice of the moon." He tore apart the expert's credentials and testimony, then took over presentation of all the defense evidence and won. It was his first time in court.
A year later, a reporter asked Bailey if he would supervise a lie detector test for Cleveland Doctor Sam Sheppard, who had already been convicted of murdering his wife. Bailey agreed. To get permission for the test, Bailey mounted what became the first of his now familiar pretrial publicity campaigns. Appearing on a TV talk show, he used a lie detector to uncover the most burning secret of the day: that Johnny Carson would be Jack Paar's replacement on nighttime TV. The tactic did more for his ego than his client. The ploy hardened official resistance, and a state court declined to order the polygraph.