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Cunningham rides to Dignam's funeral in a carriage with Mr. Power, Simon Dedalus, and Leopold Bloom.
When the men call out to a Jewish man in the street and make fun of him, Cunningham says that they have all felt the animosity of a Jewish moneylender. He then remembers Bloom and says that almost all of them have.
When Mr. Power and Simon Dedalus start talking about the disgrace of suicide, Cunningham, knowing that Bloom's father committed suicide, says that they must take a sympathetic view and that it is not their place to judge.
Bloom thinks kindly of him and recalls hearing that his marriage is a nightmare. Cunningham takes care of his wife all week only to have her pawn their furniture on the weekend.
Once they are out the carriage, Cunningham chastises Mr. Power for speaking of suicide before Bloom. Power says he didn't know.
At the end of the chapter, Cunningham is with Menton when he snubs Bloom. When Menton does not acknowledge Bloom's comment that there is a dent in his cap, Cunningham points out that this is actually is the case.
Episode 10: The Wandering Rocks
Cunningham has taken up a collection for Patrick Dignam. He attempts to spread the word around turn, and announces to the other men that Bloom has made a five-shilling donation. They all joke about it.
Episode 11: Sirens
At the end of the episode, Bloom remembers his meeting with Cunningham at 5pm.
Episode 12: Cyclops
The whole reason Bloom goes to Barney Kiernan's pub is to meet with Cunningham over some insurance business of Dignam's. By the time Cunningham gets there, Bloom has ducked around the corner, and all the men in the bar are disparaging him violently.
When Cunningham first comes in, he asks for Bloom. Lenehan says that he's busy defrauding widows and orphans. Wyse spreads the rumor he's been telling that Bloom first clued the writer Griffith into Sinn Fein.
Cunningham says that these things are just alleged.
O'Molloy jokes that that would only work if Bloom knew which country he was from. Lambert starts asking what exactly Bloom is. Cunningham does his best to set the story straight, but they're all very against Bloom by now.
The citizen cries, "That's the new Messiah for Ireland" (12.489)!
Cunningham says, "Well, they're still waiting for their redeemer. For that matter so are we" (12.490).
As their talk of Bloom reaches a higher pitch, Martin asks them to be charitable. They ask Martin to have a drink. The citizen continues to rail against Bloom.
(This episode is filled with parodies and each one is denoted as such.)
PARODY: As Cunningham says a blessing before they drink, the passage takes on the style of church news coverage of religious festivals, and offers a vision of the Island of Saints and Sages.
Cunningham blesses everyone in Latin.
Bloom comes back in and tells Cunningham he has been looking for him. The citizen makes a dig at Bloom, and Cunningham, seeing things are about to get out of hand, quickly leads Bloom and his other companions out.
PARODY: As Cunningham tells the carriage-driver to get ready to head on, the passage is again written as a late-19th century romantic version of medieval legend.
Episode 15: Circe
In Bloom's masochistic fantasy, Cunningham appears as the foreman of the jury that condemns him for being a lewd man.
Later, Bloom looks in a mirror in Bella Cohen's brothel and has an image of Cunningham being nagged by his wife.