As he was an ambitious youth, it should come as little surprise that Jefferson ended up falling in love with a woman well beyond his ways and means. Twenty- three-year-old Martha Wayles Skelton was the daughter of a prominent Virginia lawyer and speculator named John Wayles, and the widow of Jefferson's classmate at William and Mary, Bathurst Skelton. Jefferson found Martha especially attractive because of her education and her penchant for music. Throughout their courtship of 1770 and 1771, the young couple would frequently harmonize together, she singing while he played accompaniment on piano.
Despite the objections of Wayles, who felt Jefferson too modest to make a profitable match, the two ultimately made a duet too well paired to be put off. After a lengthy and lavish shower of accoutrements and affections, Jefferson won Wayles over and was married to Martha on New Year's Day 1772. The wedding, held at the Wayles estate, The Forest, was presided over by a pair of Anglican priests, and followed up by a fortnight of revelry. In the end the newlyweds were forced to steal away from the lingering festivities amidst a violent snowstorm, which they fought all the way back to Monticello.
More than a bride, in gaining Martha Wayles Skelton, Jefferson gained access to what would become a monstrous inheritance. In the eighteen months between his marriage and the death of his father-in-law, Jefferson watched as the Wayles fortune turned sour amidst a series of bad business deals, not all of them square. In the end, Jefferson was left with the majority of Wayles' holdings, but also the majority of his debt.
By the time the dust settled, Jefferson found himself in charge of combined estates that included over 10,000 acres and 130 slaves. Added to his prior holdings, this put him in upper echelon of landed and slave-owning gentry in Virginia. Such a distinction must have come as a mixed blessing to Jefferson, who had already gone on record with his philosophical objections to slavery. He would continue to condemn the peculiar institution in the abstract throughout his life, all the while continuing to function as a large-scale slave-owner.
Beyond the philosophical complications of slavery, Jefferson's troubles as a slave-owner also had a psychological dimension. This was so on account of his father-in-law. Like many widowed aristocrats in Virginia, Wayles had turned to one of his female slaves for comfort and companionship toward the end of his life. And, like her mother before her, Betty Hemings gradually found herself locked in as long-term mistress to her master. In all, she would bear several children to Wayles: some estimates range as high as six. Thus, when Jefferson inherited Wayles' holdings, he found himself in the complicated situation of possessing a family of slaves who were the unacknowledged half- siblings of his spouse. Such an odd arrangement would eventually prove to have life-changing effects for Jefferson.
More immediately, in order to pay off Wayles' debts, Jefferson dispensed with a portion of the inherited lands and slaves, and chose to funnel what few resources he could gather into the improvement of Monticello. Throughout the remainder of his life, Jefferson would value the improvement of lands and the possession of slaves over the retention of capital. While his lands and slave populations fluctuated, he was always under demands from his creditors. The constant additions and renovations to Monticello, coupled with Jefferson's extravagant tastes and bent for playing host, would keep him in a constant spiral of debt that he never recovered from, and until the very end, seemingly never cared to.