In August, 1654, therefore, Cromwell made up his mind to send an expedition to attack the Spanish settlements in the West Indies. General Venables, who was chosen to command it, showed scruples about the justice of attacking the Spaniards. He was told, “that if we had no peace with the Spaniards, then this could be no breach of the peace; if we had peace with them, they had broken it, and then it was but just for the English to seek reparation.”
Cromwell did not believe that war with Spain in the West Indies would necessarily lead to war with Spain in Europe. There were many precedents and the practice of the Spaniards themselves to the contrary. The old Elizabethan maxim, “No peace beyond the line,” seemed still to hold good. Still more powerful was the recollection of the treasures which the Elizabethan sailors had brought home. What if Spain did declare war? It would be easy to intercept the galleons which brought the silver of Peru from Porto Bello to Havana, and from Havana to Spain. A war with Spain was the most profitable of all wars, and at the worst the profits of the captures would defray the cost of the expedition.
In December, 1654, a fleet of thirty-eight ships, commanded by Admiral Penn, sailed from Portsmouth, bearing General Venables and twenty-five hundred soldiers. With them also went Edward Winslow, once governor of Plymouth Colony, now one of the commissioners appointed to assist Venables in the conduct of the expedition. As the New England colonies had been called on to contribute to the conquest of the Dutch, so the West Indian islands were expected to co-operate in the enterprise against the Spaniards. Nor were Cromwell’s expectations disappointed. At Barbadoes and elsewhere, Venables enlisted enough to raise his army to seven thousand men. Some took service in hopes of plunder, expecting to gain “mountains of gold.” With others, the desire for new lands was the chief incentive. St. Kitts, “an island almost worn out by reason of the multitudes that live upon it,” furnished eight hundred men. But, though the army was large, it was of bad material, badly armed, half drilled, and with very little discipline. The officers knew little of their men, and the old soldiers, drafted from the different regiments in England to form the nucleus of the force, were not enough to leaven the lump. In April, Venables effected a landing on Hispaniola, and marched through the woods to attack its capital, San Domingo. The Spaniards had stopped up the wells, and the soldiers, who had no water-bottles, were worn out by thirst and fatigue before they came in sight of the town. Twice they fell into ambuscades, and were shamefully repulsed by a handful of Spaniards. In the second defeat, they lost eight colours and four hundred men, while Major-General Heane, disdaining to fly, fell pierced by a dozen Spanish lances as he strove to rally his broken regiment. Heavy rains and bad food completed the disorganisation of the troops. “Never did my eyes see men more discouraged,” wrote Venables, and when a third attempt was proposed, the officers declined to lead their men, but offered to try to take the town without them.