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When Charles I was beheaded in 1649, it was as if the monarchy itself had been executed. It came at a time when planters and settlers throughout the colonies wanted stability. For many of them, here was a warning that they should be divorced from what was taking place in England. Civil War was possibly bad for business and it could be that Cromwell would want to impose military rule over them to guarantee loyalty.
Not surprisingly, many planters wanted to distance themselves from events in Britain. Barbados for example had a militia but was not good enough to repel Cromwell and not rich enough to declare independence.
Barbados is a very good example of the colonists' Civil War dilemma. In 1650, Francis, Lord Willoughby of Parnham arrived to claim the island in the name of Charles Stuart the pretender brother of the executed Charles the First. After initial protest, Barbados proclaimed Charles Stuart King of England. This was treason. But not all Barbadians were royalists; those who were not were told that, as roundheads, they should go back to England. The island was thus split, just as England was.
The Barbadians about to be deported from the island were being kicked out of their homes. Back in England, they would be political exiles. Cromwell sent Sir George Ayscue [AYSCUE CORR.] to bring order. There was a long stand-off and it took until 1652 before the islanders backed down. But Barbados was not alone. Every colony was under suspicion and had to decide if it wished to be in rebellion. The islands had to accept that times had changed and the best thing to do was to wait for what they believed was inevitable, the Restoration. It finally came in 1660.
Lord Willoughby of Parnham opposed Charles I at the start of war & in 1643 became a successful Parliamentarian commander until 1644. Speaker of the House in 1647, he opposed the idea of Cromwell's new Model Army. He was imprisoned and, when released, went to the Netherlands to join Charles and became a vice admiral. Charles, in exile, appointed Willoughby Governor of Barbados. He sent an expedition to Suriname where Fort Willoughby was named after him. Willoughby resisted Ayscue's blockading until seeking a truce, after which he was replaced as governor and was allowed to return to his English estates in 1652. On the Restoration he was made governor of St Kitts, Nevis, Montserrat and Antigua. In July 1666, he attempted to re-capture St Kitts which had been taken by the French. His fleet was destroyed by a hurricane and he drowned.
When Cromwell went to war with Spain, he was advised that he could easily take Cuba and Hispaniola. These were strategically important to Cromwell's navy if it was to harass Spanish ships between the Americas and Europe. The British attack on Hispaniola in May 1655 was a fiasco. So Cromwell's Admiral Penn and General Venables instead attacked the weak, and at that time, unimportant island of Jamaica. The Spanish fled but not before freeing all their slaves, the Maroons, who took to the hills and they and their descendants continued to attack the British settlers until well into the 18th century. Jamaica therefore was the only Caribbean colony that was taken for military and political reasons and not for commercial profit.
Reaction to the execution of King Charles I in Barbados in May 1650 and published Statute, which banished non-conformist citizens of the island.
"...by a Statute lately enacted and published within this island it was declared that all Independents, non-conformists to the doctrine and discipline of the Church of England, and others and their aiders and abettors in the disturbance of the peace of this Island, should besides their Fines depart from hence within three months; and that till then the guards of horse and foot were ordered to be kept for the security of the island, which Guards are since found to be a matter of great charge, and to bring many other inconveniences to the inhabitants. For the speedy freeing of the country from these aforesaid great charges and fears, such of the said independents and their adherents as are hereafter nominated shall depart this island on or before the second day of July now next ensuing, under pain of confiscation of their whole estates and incurring the further censure of the governor and council."
