While Shaw never met Queen Victoria, his sovereign during the first forty-five years of his life, the degree of her influence is apparent in Shaw’s reference to himself, in his ninth decade, as "an old Victorian." Weintraub explores those in the literary world who interacted with Shaw, such as H. L. Mencken, one of Shaw's earliest American fans, who turned against his hero at the peak of his translatlantic reputation, and James Joyce, who was loath to confess his respect for his fellow Irishman. He investigates the curious mutual admiration between Shaw and W. B. Yeats and Shaw’s championing of Oscar Wilde despite the vast difference in their lifestyles.

Weintraub's skillful investigation of each of these twelve relationships illuminates a different facet of Shaw, from his pre-dramatist years in London through the close of his long life.