Mr. Chesney has been the postmaster of Greenwood falls for about as long as Hannah Fairchild can remember. He has a long history of hating children, and every kid in town hates him just as much. He is known to yell and threaten the kids, especially if they're near the alleyway of the post office, or on his property. On one Halloween night, Hannah and her friends planned to spray paint Mr. Chesney's windows, only to see him waiting outside his house, shotgun in hand, ensuring nobody tried anything that night.
When Hannah walks through town one day, she sees a confrontation going on in the alleyway of the post office as Mr. Chesney is yelling at Danny Anderson and his friends Fred Drake and Alan Miller and throwing stones at the dog of one of the boys. Later, after the boys steal ice cream cones, they stop at Mr. Chesney's house. Fred and Alan dare Danny to steal his mailbox, but before the kids can grab it, Mr. Chesney arrives and grabs them. The three manage to make a run for it, not before Mr. Chesney threatens that if they show up again, he'll shoot them with his shotgun.
The boys, now more furious than ever, vow to get revenge on Mr. Chesney. They sneak into his house when he leaves, but in the middle of whatever their plan was, they accidentally set the house on fire. Fred and Alan escape, while Danny is still stuck in the house. Hannah manages to rescue Danny in the nick of time, this being the good deed she needed to do on Earth before being reunited with her family in the afterlife.
Unlike his portrayal in the book, Mr. Chesney is nowhere as mean in the television adaptation. However, he tends to be more bumbling and ignorant to his surroundings at times. When he first appears, he is barely paying attention to the road, almost running over Danny with his mail truck. Later, while at his mail truck, he is unable to see Hannah due to her being a ghost. But when she lifts his mail bag in the air and dumps the contents, he reacts in fright and runs off. Danny is dared by Fred and Alan to throw a stink bomb in Chesney's house while he's asleep. However, everything goes wrong and the house catches fire with Danny trapped inside. Chesney at first runs out with his cat, Beauregard , not noticing the unconscious Danny, but when Hannah plays the piano, he hears the music and reenters his house, rescuing Danny.
In the book, Mr. Chesney is always angry, especially around kids. He is also extremely paranoid, and will usually threaten kids with his shotgun to ward them away from his property. This is due to many of the kids in town trying to vandalize his property. In the episode, Chesney isn't portrayed as mean, but instead as more bumbling. He doesn't seem to have a problem with kids, but kids often try to mess with him anyway, usually as a way to initiate new kids.
In the book, Mr. Chesney is described as a thin, red-faced man with a bald head with a brown mustache under his pointy nose. In the episode, he is an average weight man with a shaved head of dark hair.