Possible Clues:

• Clinton, Bush or Cheney
• New Haven collegian, informally
• Matriculated New Havenite
• "The Whiffenpoof Song" collegian
• Bulldog loyalist
• George H. W. Bush or George W. Bush
• Collegian whose school mascot is Handsome Dan
• Secret society inductee, perhaps, I'll never tell ;)
• 'Baa! Baa! Baa!' singer
• New England collegian