The term 'Letter Man' can be broken down into four crossword solutions: Postmaster (10 letters), SIR (3 letters), Sajak (5 letters), and Penpal (6 letters). Postmaster is a job title for someone who is responsible for sorting, delivering, and collecting mail. SIR is a polite form of address used when speaking to a man of higher social status. Pat Sajak is an American television personality best known as the host of the game show Wheel of Fortune. Penpal is a person with whom one exchanges letters, typically by mail.