At his retirement, Edmund left his business in charge of his oldest son Robert who was also a member of the Grocer's Guild. Edmund's brother Robert was supposed to purchase for this nephew a baronetcy and he was to have the lands purchased by Edmund which were in the possession of his uncle Robert. Edmund's second son, Edmund was given lands at Bromley, Kent. It was in the plans of his uncle, Robert to make him a baronet as well. The youngest son, Thomas, was to have the family tobacco business in Virginia and in Middleburg, Holland. The Pearsalls at Horsely in Staffordshire (Edmund and Robert's old home) cast their lot with Thomas in the tobacco trade.
As long as the Pearsalls had the monopoly on the tobacco trade, it proceeded decently and in order and with increasing profit to all involved. When the grant of monopoly expired in 1620 and the Virginia Company was formed, everything changed. Profits were so wildly appealing that smuggling and black market trading abounded. " A time when the officers of foreign vessels of war actually engaged in smuggling tobacco, both out of Virginia and into their own country, without paying either the impost of Virginia or the tariff of their own country." (Ibid. p.889)
The Virginia concession was expanded to include the "Summer Isles" in 1620 to get around the British rule limiting the import of tobacco to that country. Importing tobacco through the family office in Middleborough, the English colony in Holland made us truly "Dutch/English" traders. Middleborough was a place of sojourn for the Puritans before they reached America as well.
Holland imposed its own taxes on tobacco and the only way to continue the profitable trade in this commodity was to evade these costs. The control of the tobacco trade went then to the Chesapeake Bay country. Thomas Pearsall settled in Virginia in the Isle of Wight Country to manage the tobacco trade there. Collection of the tobacco taxes for the royal treasury fell short. In order to collect them more efficiently, local control in the colony was granted with locally collected tobacco taxes to be sent to the crown. The officers tried diligently to collect the taxes, but the geography of the area favored the smugglers.
Back in England, the aged Edmund Pearsall who came out of retirement at the urging of his brother Robert Peshall of Bloor Pipe was speculating in land and money. He had lost his mastery of the business of financier. Meanwhile, Robert was falsely claiming and borrowing on his brother's land and defrauding his brother of the rents. After Robert's death, the lawsuits were continued with Robert's daughter and heir and Elizabeth's husband Sir Humphrey Styles continued these suites and pressing the claims now in Robert Peshall's will as their due. These claims together with the business losses swallowed one of the larger fortunes in England and ended with Edmund Pearsall in Fleet Street Prison for debt. He was aided somewhat by the Grocer's Guild with a small pension. He died in April 1629 on the same day as his son Edmund (also in Fleet Street prison) died surrounded by the members of the Pearsall family.
Sir Humphrey Styles was made Cup Bearer to King Charles I. He used his position to influence the arrest of Edmund Pearsall the Younger by the Star Chamber and the subsequent confession under torture causing the forfeiture of court claims to the family estates and fortune. As a result of the attentions of Archbishop Laud and of the prison inquisitors, Edmund also died in the Fleet Street prison in the company of the relatives gathered at the deathbed of his father.
Sir Humphrey lost all that he had gained in the courts. At the beheading of the king, the property of Royalist supporters of Charles I was seized.
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