Another reason concerned Robert E Lee's financial condition. His mother was dying, and his father, who left the country in 1812, had long since wasted the small fortune acquired from his first wife, Matilida Lee. "Light Horse" Harry spent a year in debtor's prison when young Robert was two. Ann Carter Lee supported her children on an endowment from her father, an interest-bearing investment with the Bank of Virginia. Mr Carter hired a good attorney who made sure that Robert E Lee's father could never touch the money. Henry Lee could not support his family and abandoned his wife and children.

Yet another reason Mr Custis may have been reluctant to allow his daughter to marry into the Lee family involved a civil case against "Black Horse" Harry Lee, Robert's oldest half-brother. Because of the subject matter I hestitate to go into detail here. However, the substance was strong enough to have President Jackson's appointment for him as an ambassador to be rejected by the Senate in August 1829. Robert E Lee had nothing to do with his half-brother's character and reputation, but suffered for it nonetheless.