Mr. Dalton, a wealthy Chicago real-estate mogul, earnestly and proudly believes that he is a friend of the Black community. He is a regular donator to the NAACP. He tells this to Bigger, but Bigger doesn't know what he's talking about:

"I want you to know why I'm hiring you."

"Yessuh."

"You see, Bigger, I'm a supporter of the National Association for the Advancement of Colored People. Did you ever hear of that organization?"

"Nawsuh."

"Well, it doesn't matter," said Mr. Dalton. "Have you had your dinner?"

That Mr. Dalton says "it doesn't matter" is indicative of his real position: charity actually doesn't matter to Mr. Dalton. While Mr. Dalton feels that he supports the Black community in Chicago, in fact his charity is largely ineffective and only serves to support his ego. In fact, Mr. Dalton's work actively harms the Black community through his unfair real estate practices. As such, this is an example of situational irony: while Mr. Dalton says he helps Black people, he actually hurts them.

This irony is revealed when Mr. Dalton's business dealings are clarified in Book 3. When the Daltons visit Bigger in his cell, Mr. Dalton and Max argue over what the former feels is a helpful donation:

"Why, only today I sent a dozen ping-pong tables to the South Side Boys' Club ..."

"Mr. Dalton!" Max exclaimed, coming forward suddenly. "My God, man! Will ping-pong keep men from murdering? Can't you see? Even after losing your daughter, you're going to keep going in the same direction? Don't you grant as much life-feeling to other men as you have? Could ping-pong have kept you from making your millions? This boy and millions like him want a meaningful life, not ping-pong ..."

Mr. Dalton proceeds to defend himself, claiming that it is not his responsibility to save all Black people from poverty and that the state of the world is not his fault. This is a rather distasteful stance, but many well-meaning wealthy men make charitable donations with little strong feeling behind them—the ping-pong tables do not represent a situational irony on their own. But when Max cross-examines Mr. Dalton, whom Buckley called as a witness for the prosecution, the reader learns of a deeper level of irony. Mr. Dalton's company is actively hurting Black communities, including Bigger and his family. Max's question reveals the problem:

"Now, Mr. Dalton, it has been said that you donate millions of dollars to educate Negroes. Why is it that you exact an exorbitant rent of eight dollars per week from the Thomas family for one unventilated, rat-infested room in which four people eat and sleep?"

Herein lies the irony: while Mr. Dalton claims to help Black people, his South Side Real Estate Company charges Black families more for the same houses rented to white families. He will only rent to Black families in certain parts of the city, because of "old custom." The Thomas family lives in Dalton's housing, and, according to Max, Bigger's personality—his neurotic fear of white people, his need for action—was caused in no small part by his poor housing situation. Mr. Dalton's charity, thus, is situationally ironic: he thinks he is helping Bigger and the Black community through his hiring practices and his charity. But in reality, he only gives them ping-pong tables and rat-infested housing.