Mr. Smiley is a man who is assigned to lower suicide rates in prisons by Dr. Money. He seems upbeat and happy. He is very friendly to the prisoner. During Day 2, the player receives a letter addressed to Mr. Smiley, revealing that his daughters were kidnapped and used as blackmail. In an attempt to please the protagonist, Mr. Smiley sends the protagonist these items: Doctor Money Portable Entertainment Product, five confetti poppers, five games, and a poster.
On Day 5, Mr. Smiley tells the protagonist his true motive for getting him presents, and reveals that his daughters had already died because of the infection. He then sells his organs to buy the protagonist one final game and to commit suicide.
Mr. Smiley says that he was never the player's friend, but this may be false as he kills himself in a way so he can buy the player a final game rather than simply killing himself.