Miles is the narrator of the novel and has a fascination with biographies and the last words of notable figures. The last words attributed to the poet Francois Rabelais are “I go to seek a Great Perhaps” and this expression becomes emblematic for Miles, who leaves behind his humdrum existence in Florida and starts afresh at Culver Creek. His father had attended this same school, which is partly the reason for his decision. However, he is also keen to embark on a new life of excitement and take part in the kind of adventures and pranks that notable figures (such as John F. Kennedy) engaged in during their days at boarding school.

The “Great Perhaps” provides Miles with a source of motivation, and he settles in quickly. After hitting it off with his roommate, Chip (aka “the Colonel”), he finds himself part of a close-knit circle of friends and experiences a life of fun and mischief. He is not as confident as the Colonel or as much of a natural leader, and he acquires the ironic nickname “Pudge” on account of his slight frame. However, he is content to serve as the Colonel’s sidekick for the time being, and the two become firm friends.