Possible Clues:

• Skip Day participant
• Fourth-year college student
• Old Spanish chap embraces leader from Italy
• High-class pupil?
• Student involved in a "skip day," maybe
• Old cronies abandoned leader and fell into disarray
• I snore badly, getting older
• No rise, strangely, for one of higher rank
• High-ranking head of Inquisition appearing in Man of La Mancha?
• & 17 Down More than one 19 potentially from 2 & 14, 6 & 20 or 8 & 24