Thomas Gage, a Catholic priest who became a zealous ally of Oliver Cromwell, played a crucial role in the creation of what was to become Britain’s Caribbean empire. It did not appear so at the time, though, and he was not to realise it, for his unlikely encounters with the Lord Protector led to his own death and would deal a mortal blow to the Protectorate regime.

Gage was born into a long-established recusant family in Surrey: both his parents had been condemned to death and then reprieved for harbouring Catholic priests, while an uncle had been executed for his role in the Babington Plot to assassinate Elizabeth I in 1586. Robert Southwell, the Jesuit martyr, was a cousin.

Gage, like most bright sons of recusant families, entered the Catholic seminary at St Omer in northern France at about the age of 12. His father intended him to enter the Society of Jesus, but having moved on to the ‘hispaniolated’ English College in Valladolid, where he opted for a friar’s life in the Dominicans; his father disowned him in response.

Englishmen, even of the Roman faith, were banned from travelling in the imperial possessions of Habsburg Spain, but somehow, in 1627, the insatiably curious Gage, then at a convent in Jerez and known as Tomàs de Santa Maria, boarded a ship in Cadiz bound for Mexico. There he was to begin the next stage of his journey, to Manila, capital of the Spanish Philippines. But instead, Gage, along with some fellow friars, headed south to Chiapas and then on to Guatemala, his ‘second patria’, and its then capital city, Antigua, where he was to spend the next decade. A natural linguist, Gage spent lengthy periods of time among the Pokoman Maya, making notes along the way for what would become the first account by an Englishman of life in Spain’s New World.

By January 1637, Gage had begun a long and hazardous journey back to Europe. Robbed by Dutch pirates on the Mosquito Coast, in what is now Belize, he crossed to the western Pacific side of the Central American isthmus, from where he sailed to Panama, eventually reaching the major Spanish port of Portobello on the Caribbean coast. Here, he enrolled as chaplain to the captain of the ship that would return him to Spain. A month later, having forgotten most of his native tongue, he arrived in England, disinherited by his father, and dependent on the recusant underground protected by Henrietta Maria, Charles I’s queen. He reportedly said Mass for a final time at a clandestine chapel in Holborn.

After travelling to Rome and escaping the clutches of French privateers, he returned to England for the last time in 1640. It took him two years, unsurprisingly, to convince Anglican bishops of his conversion to the Church of England’s puritan wing, a move he announced at St Paul’s on 28 August 1642, in a sermon later published as The Tyranny of Satan Discovered in the Tears of a Converted Sinner. A sympathetic Parliament granted him a parish in Kent, before he moved to a more substantial position at the church of St Leonard’s in the Kentish port of Deal, where he married – one of the benefits of conversion –Ellen Yatt. They raised at least three daughters.

There Gage composed his compelling travelogue of retrospective self-justification, The English-American his Travail by Sea and Land, or, A New Survey of the West Indias, eventually published in England in 1648. This was not only the first account of life in the Spanish New World by an Englishman, it was the first by a non-Habsburg subject.

A best-seller in its day, it remains an enjoyable read, despite its breathless paragraphs. Food is an obsession with Gage, no doubt due to the long periods of privation he endured. One chapter is devoted entirely to chocolate, which fascinated him, though he observed that ‘those that use this chocolate much grow fat and corpulent by it’.

Elsewhere, he describes, for the first time in English, burritos and tamales, as well as other local delicacies, such as beans and iguana, and writes sympathetically of the Indians who prepared them: a pastoral priest, he was plainly committed to caring for his indigenous flock.

The bitter divisions of Civil War revealed a less attractive side. Gage bore witness in court against three of his former colleagues: Father Thomas Holland, who he had known at St Omer, was executed in 1642 largely on Gage’s evidence; Father Arthur Bell, who was chaplain to one of his cousin’s, met a traitor’s death a year later; and in 1651, Father Peter Wright, the chaplain of his elder brother, the royalist cavalry officer Henry (who ‘strove to eliminate all memory of him’). His brother had died in the arms of the priest in battle in 1644. He even testified against his younger sibling, George, also a priest, who judged him a ‘graceless brother’, whose actions ‘our whole family doth blush to behold’.

With the zealotry of the convert, Gage defended the Protectorate’s religious settlement in his 1654 work, A Full Survey of Sion and Babylon. Around the same time, encouraged by the regicide Thomas Chaloner, Gage submitted a proposal for an English expedition to the heart of the Spanish Caribbean and, according to reports by the Venetian ambassador and Bishop Gilbert Burnet, held secret meetings with Oliver Cromwell, then established as Lord Protector.

Gage argued that the strength of both the House of Habsburg and, by extension, the papacy, was wholly dependent on the resources of the New World: ‘The Austrian pillar’s strength … be in the American mines; which being taken away with Austria, Rome’s triple crown would soon fall and decay.’

‘The Spaniards cannot oppose much,’ Gage continued, ‘being a lazy sinful people, feeding like beasts upon their lusts, and upon the fat of the land’. He was playing to the stereotype of England’s Catholic antichrist, which reached back to the days of the Armada.

Cromwell should not miss such an opportunity to beat the Spanish in their New World, urged Gage. He should recall the mistake of Henry VII, who had turned down the chance to fund Columbus. ‘God would not make that prince such an instrument for the advancing glory, as he hath made your highness’, Gage implored, handing down a gauntlet.

Encouraged by Gage, Cromwell’s council met in April 1654 to discuss how England , with ‘160 sail of ships well appointed swimming at sea’, might employ its substantial military resources to ‘some advantageous design’. The gatherings were memorable for the clashes between a confident, belligerent Cromwell and his more cautious colleague, John Lambert, the regime’s second most powerful figure. Two months later, Cromwell having won the debate, the Council gave secret orders to the Admiralty to prepare 14 ships for what came to be known as the Western Design.

By the beginning of July, 36 ships had been approved for the assault on the Spanish New World. There were to be joint commanders of the expedition. William Penn, was to be General-at-Sea, while General Richard Venables was to command the land army. They set sail from Spithead in the Swiftsure on Christmas Day 1654, along with 37 other ships, some support vessels and around 2,500 men. They would follow the example of Francis Drake and attack the island of Hispaniola, now shared between the nations of Haiti and the Dominican Republic.

The Western Design met with catastrophe when its forces landed at Hispaniola, in challenging surf, in April 1655. A regime that had never known defeat saw providence turn to hubris almost overnight. The force was ill-prepared for tropical conditions, lacking adequate clothing, weapons, food and water. The indigenous peoples did not, as Gage had predicted, turn on their Spanish masters. Rather, they fought hard for them, particularly the vaqueros, or ‘cowkillers’, men and women of partly African descent whose deployment of ferocious lances was athletic and highly skilled. Many of these lances were ‘sheathed in the enemy’s bowels’. Altogether, around 1,500 English troops died. Only a few fighting seamen came anywhere near Hispaniola’s capital San Domingo. It was a military disaster of the first order.

Penn and Venables tried to save face by heading for Jamaica, one sixth the size of their original target. It was a poorly regarded afterthought, home to around 2,000 Spanish, Portuguese, African and Indigenous people. But, downwind and accessible from the south coast of Hispaniola, it offered a redemption of sorts.

Luckily, for Penn, Venables, as well as Gage, who was in their party, Jamaica was the only undefended Spanish possession in the Caribbean. It was the last personal possession of the Columbus family, who claimed rent but little else and argued that Spanish royal law forbade the building of unlicensed fortifications.

Forty English ships entered what became known as Old Harbour Bay on Jamaica’s south-central coast on 10 May and, despite bitter if chaotic resistance, its Spanish occupiers surrendered a week later, though not before various guerrilla forces took to the hills: it would take decades to pacify the island. While attempting to flush them out, Venables became affected by fever. Penn abandoned him and set sail for home on 25 June. Gage would stay in Jamaica and die there early in 1656, like half the island’s English garrison, of malaria and dysentery. No one realised that Jamaica would become Britain’s most important Caribbean possession, where the horrors of slavery would come to dominate a settlement founded by men who proclaimed liberty.

When in October 1655 news had reached Cromwell of the failure of the Western Design, a project he owed to Thomas Gage, he turned penitent before his God: ‘We have provoked the Lord and it is good for us to know so, and to be abased for the same … we should  …  lay our mouths … in the dust.’ God was punishing England, His chosen people, for their sinfulness, their hubris, a people ‘circumcised, but raw’. They were on their way to the promised land, but they were not there yet. A moral reformation would be enforced and sinfulness punished. In doing so, the seeds of the regime’s downfall would be sown. Thomas Gage was a man of unintended consequences.