At his own expense, John Vassall fitted out two ships, The Samuel and the Little Toby, which he commanded against the Spanish Armada and later invested in the Virginia Company.
[2] Vassall launched his career as a merchant for the Levant Company, trading Ottoman goods including rum, spices, opium, cloth, tin, and pewter in Europe.
"[5] In September 1628, Vassall was imprisoned and his goods retained when he "refused to pay to the custom-house the tonnage and poundage on a large quantity of currants which he was importing.
"[6] In June, he again contended against tonnage and poundage requirements, "having brought from Virginia to Tilbury a vessel laden ‘with that drug called tobacco'", and in September, he advanced £50 to the Massachusetts Bay Company.
[8][7] One 1651 instruction by the Guinea Company "asked a captain to ‘put aboard...so many negers as your ship can carry,'" apparently for enslavement in England, while another read, ‘We pray you buy as many lusty negers as she will can carry, and so despatch her to the Barbadoes'",[9] where Vassall's brother William owned a sugar plantation, taking advantage of the "rapid and immense fortunes to be accrued.
"[10] For nearly 200 years following his arrival, "the [Vassall] family built its wealth by running slave-labor plantations in the Caribbean" where they were among the "leading planters.
[13][14] In June of the same year he was summoned together with Richard Chambers by the council in order to be ‘committed to some prisons in remote parts for seducing the King's people'.
In 1642 he was one of the commissioners for plantations in the American colonies, and as such in November took part in the appointment of Sir Thomas Warner as governor of the Caribbee Islands.
With regard to Vassall's attempts to secure compensation for his losses and imprisonment, the matter was referred on 14 June 1644 to the committee for the navy, and on 18 January 1647 the commons voted him £10,445 12s.
On 6 April 1654, in a petition presented to the Protector, he stated that as a result of resisting tonnage and poundage he had lost £15,000, and begged leave to refund himself by means of privileges to import French wines, ship coals and lead, or receive forest land.
He was nevertheless informed on 8 September 1657 that he should make his application for payment to parliament, "as no revenue remains at his highness's disposal to satisfy the said debt."
In 1663 Vassall was in Carolina making arrangements with the lords proprietors of the colony regarding a claim laid by him for part of a term not yet expired.