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In 1664 Charles granted a licence for five years to Sir James Modyford, brother of Sir Thomas, to take all felons convicted in the circuits and at the Old Bailey who were afterwards reprieved for transportation to foreign plantations, and to transmit them to the governor of Jamaica; and this practice was continued throughout the whole of the buccaneering period.

He was but thirty-three years old when he led the expedition against Porto Bello. In the beginning of 1668 Sir Thomas Modyford, having had "frequent and strong advice" that the Spaniards were planning an invasion of Jamaica, had commissioned Henry Morgan to draw together the English privateers and take some Spanish prisoners in order to find out if these rumours were true.

When Barry landed on Tortuga, however, with no other support than a proclamation and a harangue, the French inhabitants laughed in his face, and he returned to Jamaica in shame and confusion. On 4th January 1664, the king wrote to Sir Thomas Modyford in Barbadoes that he had chosen him governor of Jamaica.

In significant contrast to Lord Vaughan's praise of Lynch, Sir Henry Morgan, who could have little love for the man who had shipped him and Modyford as prisoners to England, filled the ears of Secretary Williamson with veiled accusations against Lynch of having tampered with the revenues and neglected the defences of the island.

On receiving his commission and instructions he immediately prepared letters to the President of San Domingo, expressing his fair intentions and requesting the co-operation of the Spaniards. Modyford himself arrived in Jamaica on 1st June, proclaimed an entire cessation of hostilities, and on the 16th sent the "Swallow" ketch to Cartagena to acquaint the governor with what he had done.

All of the ships but three, however, were eventually got off and repaired, and on 6th December Morgan was able to write to Modyford that he had 1800 buccaneers, including several hundred French, and thirty-six ships under his command.

However, although the governor wrote home in the latter part of the month that the privateers were entirely suppressed, he soon found that the task was by no means a simple one. Two buccaneers with a commission from Modyford, an Englishman named Thurston and a mulatto named Diego, flouted his offer of pardon, continued to prey upon Spanish shipping, and carried their prizes to Tortuga.

After the decision of the council of officers on 2nd December to attack Panama, a boat was dispatched to Jamaica to inform Modyford, and in a letter written to Morgan ten days after the arrival of the vessel the governor gave no countermand to the decision.

On almost the same day letters were forwarded from England and from Ambassador Fanshaw in Madrid, strictly forbidding all violences in the future against the Spanish nation, and ordering Modyford to inflict condign punishment on every offender, and make entire restitution and satisfaction to the sufferers.

In the following August Modyford sent home to Bennet, now become Lord Arlington, an elaborate defence of his actions.