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Among Jackson Jr.?s bad investments was the purchase of Halcyon Plantation for which the President had to pay the first note in 1839 in the amount of $5,176. In the same year, he refused to pay a two-year overdue note amounting to $550 for a carriage; his son had lied about the purchase.
In 1840, Jackson found it necessary to restructure the obligation for Halcyon Plantation. In the same year, ill after his return from New Orleans, the father wrote to his son> ?Recollect my son that I have taken this trip to endeavor to releve [sic] you from present embarrassments, and if I live to realize it, I will die contented in the hopes that you will never again encumber yourself with debt that may result in the poverty of yourself and the little family I so much love.?
However prophetic, the above admonition had not solved the son?s credit problem, for in the same year, the President found out what he had been told was a $6,000 debt turned out to be a $12,000 obligation. To make matters worse, Jackson?s political enemies, the Whigs, made political hay of the situation.
The above debt was paid in August of 1840, but it had risen to $15,000 by the following January. Defending his son, Jackson blamed $10,000 of the debt on ?swindlers? who had taken advantage of his son. At this time, the slaves of Halcyon Plantation were cold and hungry; the plantation overseer sought legal means to recover back wages. Jackson resorted to selling off his saddle mare; he sold beef from the smokehouse. At this time, Jackson had another ward that was suffering with terminal cancer; money that had been saved for a visit had to be spent.
By 1844, Jackson Jr. was again endorsing notes for others, one for his cousin.
The following year, Jackson, now an invalid approaching death, was informed of a new $6,000 debt. Before his death, he resisted the advice of others with regard to the disposition of his estate, still favoring Andrew Jr.
'X-1. 'i i	-??-*- y
Andrew Jackson Jr. and Hancock County	'	J
May 1856
Charles Sumner, the senator from Massachusetts and an outspoken anti-slavery man, gives a vituperative speech against the pro-slavery elements in the Senate. Three days later, as Sumner is sitting at his Senate desk, a South Carolina representative, Preston Brooks, beats Sumner with a stick. It will be three years before Sumner fully recovers, but he is regarded as a martyr by Northern abolitionists - while many Southerners praise Congressman Brooks. In Kansas, late in May, pro-slavery men attack Lawrence, center of the anti-slavery settlers, and kill one man. In retaliation, a band of slavery men, led by the fiery abolitionist John Brown, kill five pro-slavery men at Pottawotamie Creek.
John S. Bowman, The Civil War Day by Day, p. 17
Eleven years after the President?s estate was settled, Andrew Jr. had resumed the patterns that would continue for the rest of his life. His debt had increased to $48,000, being the same amount which the State of Tennessee paid for the Hermitage, along with 500 acres,