Before McDonald's and Holiday Inn, Jack was on the road with his friends, when interstate highways were a novelty and going coast to coast was just for fun. Jack was pre-Vietnam, more 1950s edgy than 1960s politically correct. He loved Keats and Eliot as he sang the praises of the Odes and "The Wasteland", bars and saloons, writers and barkeeps - all about equally, according to the author, who narrates about his short time with Jack on the road. Jack was open to all subjects, more a fan than critic, and didn't see the point in being critical. "If you don't like it, why bother?" Said Jack.

The few nights detailed here relate to a Harvard College event honoring Jack. He went to high table at Lowell House, at Harvard, but clearly felt more comfortable in a South Boston style old hangout like Cronin's across the tracks... the MBTA tracks from Harvard, a 100 yards and a thousand miles.

Jack takes a trip with his young rider, and the author, up to New York to see some of Dreiser's landmarks from An American Tragedy. They get to the Adirondack area, where the actual crime happened, and Jack talks about the little glove factory still abandoned on Lake Cayuga. True? The author doesn't know, but he did know there was a glove factory and years later he went to visit it. The author comments that many people doubted what Jack said. But upon closer inspection, found him to be truthful. Jack just had a way of saying things that made the conventional nervous. Good listening for readers and listeners, not academics.