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We first hear of Mr. Deasy when he has ordered one of Stephen's students to re-copy his sums and have Stephen sign them.
Mr. Deasy is outside officiating the game of hockey. While he officiates a dispute, he asks Stephen to wait in his office for him.
Mr. Deasy comes in and pays Stephen for his work, taking all of his money out of a fancy savingsbox. When Stephen puts the money right into his pocket, Mr. Deasy tells him he will lose it that way. He suggests that Stephen get his own savingsbox.
Mr. Deasy begins lecturing Stephen about how money is power. He quotes Shakespeare on the subject, though Stephen points out that he is quoting Iago from Othello.
Deasy ignores Stephen's comment, and goes on about how the proudest thing an Englishman can say is "I paid my way" (2.115).
Deasy laughs when Stephen says that he cannot say this, and says, "We are a generous people but we must also be just" (2.121).
Deasy says that although Stephen thinks of him as an old tory, he actually has a long Irish ancestry and knows more about Irish history than Stephen does (doubtful). He claims he is descended from John Blackwood who voted for union (though it is often told that Blackwood did not support the union; he died before he could sign).
Deasy asks Stephen to deliver a letter to the newspapers for him, and types out the end of it while Stephen waits. It is on foot and mouth disease and suggests a cure that would not actually work. His argument is that since the disease can be cured, it should be okay to ship Irish cows to England.
Mr. Deasy gives Stephen the letter, and says proudly "I don't mince words" (2.144). He summarizes the argument for Stephen.
Deasy goes on to say that Jews are the national problem of England, and that "they are the signs of a nation's decay" (2.148).
When Stephen questions his prejudice, he says, "They sinned against the light. And you can see the darkness in their eyes" (2.153).
Stephen says that history is a nightmare from which he is trying to awake, and Deasy says, "The ways of the Creator are not our ways. All history moves towards one great goal, the manifestation of God" (2.160).
When Stephen suggests that God is just a shout in the street, Deasy does not seem to get his meaning.
Deasy tells Stephen that he is happier than Stephen is. He begins listing the sins of all women throughout the ages.
Deasy says that he does not think that Stephen will be at the school long. When Stephen says that he is a born learner rather than a teacher, Deasy says, "To learn one must be humble. But life is the great teacher" (2.174).
Deasy again asks Stephen to publish the article, and mentions he has sent another one to the cattletraders' association.
As Stephen heads out, Deasy says, "I like to break a lance with you, old as I am" (2.184).
While Stephen is walking away outside, Deasy runs out and tells him a last anti-Semitic joke. He says that Ireland is the only country not to have persecuted the Jews because they never let them in. He laughs disgustingly, and heads back in.
Episode 7: Aeolus
When Stephen delivers Deasy's article on foot and mouth disease, the men joke about it though Myles Crawford agrees to publish it.
As they discuss Deasy, Stephen learns that Deasy's wife is an extremely unpleasant women and he begins to understand Deasy's view of women as some of the scapegoats of history.
Episode 15: Circe
In one of Stephen's absinthe induced dreams, he imagines a ghostly re-enactment of the Gold Cup race in which Deasy is riding a particularly down and out horse.