Jack was ‘caught in an ugly middle position’ because he was caught between two difficult situations. He was unable to escape the harsh realities of life rather he tried to habituate himself to the prevailing situation. He had to manage his family with two children, his daughter Jo and his son Bobby. And hence, Jack was entangled between two worlds. The first world belonged to Roger Fish, Roger Squirrel or Roger Chipmunk where he is telling the story of a wise owl and the Wizard with a magic wand.
The world upstairs consists of his children. Jo had raised a question about whether the Wizard should hit the mommy Skunk or not. Jack was unable to satisfy her as he was very cautious about the downside world where his wife Clare was painting. The house was not well kept and the household items were scattered. They were expecting a baby and he was supposed to go and help her as she was working hard to make both the ends meet. In this way, Jack was caught in an ugly middle position between the romantic world and the real world.