Wrestling with the masters means to attempt to understand the full depth and meaning of various literature and art
work of a renown
artist. The "masters" would be defined as Steinbeck, Poe, Faulkner, Shakespeare, Homer, Johann Wolfgang von Goethe, Alexandre Dumas, Updyke, et al.
John was struggling with his English Lit. Course, he was
Wrestling with the masters, reading such works by Dumas and
Von Goethe.