The mystery of Oswald subsumes the enigma of Jack Ruby. Yet if the first mystery has haunted the American intelligence establishment with the fear that it is implicated, Jack Ruby buggers reasonable comprehension for the rest of us. A minor thug from the streets of Chicago with a mentally unbalanced and often hospitalized mother, he has Mob connections. While they are no more impressive than those cherished by a hundred thousand other petty hoodlums in fifty American cities—which is to say, connections so tenuous and yet so familial that one can make a whole case or no case out of the same material—he has grown up among the Mob, and is on a first-name basis with Mob figures of the middle ranks. He is of the Mob in the specific values of his code, and yet never a formal member in any way—too wacky, too eager, too obsessed with himself, too Jewish even for the Jewish Mob. All the same, he is pure Mafia in one part of his spirit—he wants to be known as a patriot in love with his country and his people. He is loyal. Select him and you will not make a mistake.
We all know his famous story or cover story. He was grief-stricken by the death of JFK, so bereaved that he shut down his strip-joints for the weekend, and was so appalled at the possibility that Jacqueline Kennedy might have to come to Dallas to testify in Oswald’s trial that he decided to shoot the accused—“the creep,” as he would call him. But only at the last moment did he so decide. No premeditation. At 11:17 on Sunday morning, after waiting on line at a Western Union office to send $25 to one of his strippers who was desperately in need of money, he crussed the street, went down the ramp into police headquarters, and ran smack into Oswald, who was being filmed by TV cameras in the basement as he walked with his police escort to a car that would take him to the County Jail. There, imprinting the American mind forever with the open-mouthed expression of the victim and the squint-eyed disbelief of his guards, Ruby killed Oswald. Never before in history was a death witnessed by so many people giving full attention to their television sets. Much of the world now believed that Ruby was a Mafia hit man. The logic of such an inference suggested a conspiracy not only to kill Kennedy but Oswald as well, because he knew too much.
The concept, clear as a good movie scenario, ran into one confusion that has never been resolved: Why was Ruby standing on line in Western Union waiting his turn to send $25 to a stripper while time kept floating away and Oswald might be moved at any moment? The question could not be answered. How many confederates—and most of them had to be police—would be necessary to coordinate such …
'The Amateur Hit Man' July 13, 1995