Historical clue formulations

• Much obliged? — 2024-03-30
• Behind on payments — 2023-06-13
• Way behind on payments — 2019-01-26
• Not just down — 2018-11-24
• Owing money — 2018-09-07
• Behind the eight ball — 2018-06-22
• Debt-ridden — 2017-05-14
• Trapped — 2010-12-05
• Behind — 2008-09-21
• Stuck — 2006-02-11
• Struggling — 2005-11-26
• Stuck — 2004-11-11
• Having debt — 2004-04-14
• Financially compromised — 2000-05-07
• Behind the eight ball — 2000-02-18
• Trapped — 1998-08-09