Historical clue formulations

• Person who's in the red — 2025-10-28
• One with obligations — 2025-03-06
• Bondservant, often — 2024-05-15
• Borrower — 2021-05-30
• One subject to imprisonment, in Dickens's day — 2017-12-30
• Usurer's victim — 2008-03-04
• 10-Down recipient — 1998-05-13
• One with obligations — 1995-01-08