In the poem ‘Among School Children’, poet W.B. Yeats describes himself as a ‘sixty-year-old smiling public man’ being escorted through a ‘long school room’ by a ‘kind old nun in a white hood’ where he observes that ‘The children learn to cipher and to sing/to study reading-books and histories/To cut and sew, be neat in everything/In the best modern way …’2 In these lines Yeats captures certain positive aspects of the Catholic tradition of teaching and learning that will be explored in this chapter. But there also exist negative perceptions of this tradition and these too merit exploration. One such perception is given robust expression by Peter Winn, the Princeton professor who taught Sonia Sotomayor, the first woman Hispanic member of the Supreme Court of the United States. Sotomayor, claims Winn, had to be taught very deliberately to think critically because she had come to Princeton in 1972 from a ‘Roman Catholic high school … where learning was rote and students were taught to obey authority’.3