Possible Clues:

• Oppressive boss
• Watcher or well, one is relatively large
• 'He keeps a watch, or well (3,7)'
• Relatively large or well?
• CBS reality series
• *Young boy's role model
• He may be watching you
• Frat pledge's sponsor
• Or well as a relation, to a large extent (3, 7)
• Watcher or well?