Possible Clues:

• This prisoner would be the devil outside University College
• One with very long sentence
• Second drink shortly brought up for prisoner
• Long-term con
• One may have used rifle criminally?
• Prisoner's fresh charge briefly withdrawn
• Ending in jail, I am afraid of getting no answer — am I there for ever?
• Die-hard fan no matter what, in slang
• Person sentenced to prison until death, unless paroled
• Rifle shot convict