Jim is the P.O.'s P.O. He has eased his way into a way of working which gives him a comfortable life. The women in his charge have that little bit of extra leeway. He doesn't take things too seriously and encourages his colleagues not to get too uptight about things- they're all got lives outside to get on with.
The smarter inmates on the Wing see right through Jim, but to the ordinary prisoner,like the two Julies, Mr Fenner is all right. He's easy-going and has a studied air of caring. They belive he doesen't talk down to them, and take his fake concern at face value.
Jim's a popular man with the prison officers too. They consider him wise, but not too much of a clever-dick. There's a self-deprecating front to him. He likes to say he doesn't have all the answers, although he actually belives he does.
Helen's firm-but-fair regime is too restrictive for Jim. There are too many reports, adjudications and punishments which Jim feels are petty, do nothing to promote good order and cause all kinds of hassle for him and his colleagues. Jim pretends to cooperate with Helen's regime, with a grudging acceptance. In fact, as often as he can, he subtly undermines her to his fellow officers and to prisoners alike.
Until Shell spiked his cover, Jim considered himself a very happily married man, on his own terms. He's devoted to his two children, and his wife, Marilyn, had no cause to complain. The fact that Jim's had several sexual relationships with prisoners in his care doesn't bother him too much. He can easily justify his 'pastoral' role; the women have come on strong to him, he's got what they need and he's happy to give it to them. So where's the harm ?
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