One of the first relations between Duddy and another character began at the beginning of the book.
Mr. MacPherson was distraught because of his wife’s condition on top of getting a new class to teach at FFHS. Duddy thought that class would be a walk in the park since Mr. MacPherson didn’t believe in using the whip as a form of punishment, so he began to take advantage of that.
Even though Mr. MacPherson knew that Duddy was trying to be the rebel of the class, and the “ring leader”, he saw potential, and tried to get that through to Duddy. "You'll go far, Kravitz. You're going to go very far.
" For some reason, Duddy kept on pushing Mr. MacPherson away, and continuously pushed him to the brink. Duddy once pushed Mr. MacPherson far enough for him to insult his family: "Then he's (his father) not fit to bring up a boy." Despite all the hopes that Mr. MacPherson has for Duddy, he continued to refuse the praises, and continued to cause trouble, as though it was impossible that a teacher had faith in him. One night, after coming back home from a night of drinking, Mr. MacPherson returned to find his wife Jenny at home sprawled on the floor with the phone receiver dangling loosely over her head; she later died in the hospital.
He blamed it on a prank brought upon by Duddy, "You killed my wife, Kravitz." "Stay away from me. I'm warning you." "You killed my wife." and then his complete outlook on the class and on Duddy in particular, changed.
He became very short tempered, and became a very frequent user of the strap on his students. He came into class drunk in the morning, making him the centre of every joke and insult of the classroom. Duddy thrived on knowing that he had won, he had cracked the teacher; one of the only ones to believe in him, and Duddy finds that he later was sent to a mental hospital in Verdun.Another relationship that Duddy had that is clearly troubled is the one he had with his uncle Benjy.
Uncle Benjy was always one to ridicule Duddy and his far fetched dreams. He disliked how ambitious he was in trying to get his land, calling Duddy a “scheming little bastard”. Duddy knew that his uncle preferred his older brother Lennie to him; he always showered him with gifts, and even paid his way through med school..