By the information which Oglethorpe was able to obtain from the prisoners, which confirmed the accounts received from other sources, he learned that the garrison at St. Augustine was in want of provisions; and that, the half-galleys having been sent to the Havana for troops and supplies, the river and sea-board were destitute of defence. Such being the case, he conceived that a fitting opportunity now offered for the reduction of the place, taking the enemy by surprise, before the reinforcements arrived; and thereby dispossessing the Spaniards of Florida. He, therefore, sent an express to Lieutenant-Governor Bull, urging an immediate compliance with his application for assistance. The consideration was accordingly renewed in the Assembly on the 4th of February. At length Oglethorpe, impatient of delays occasioned by their continued demurring about the feasibility of the project, presented himself before them, that they might be made acquainted more fully with his intentions, and with every thing relative to their being carried into execution. After many conferences, a scheme of action was agreed upon, and an Act of Assembly passed, April 5th, 1740, for the raising of a regiment of four hundred men, to be commanded by Colonel Vanderdussen; a troop of rangers; presents for the Indians; and supply of provisions for three months. They also furnished a large schooner, with ten carriage and sixteen swivel guns, in which they put fifty men under the command of Captain Tyrrell.

With this encouragement, and the promise of cooeperation by Commodore Vincent Price, who commanded the small fleet on that station, the place of rendezvous was appointed at the mouth of St. John’s river. The General then published his manifesto, and immediately hastened back to Georgia to prepare his forces for the Expedition.

On the beginning of April he went to the Uchee town to engage runners to his Indian allies to inform them of his intended assault of St. Augustine; to bespeak their assistance, and request their chiefs and warriors to join his forces at Frederica, whither he immediately repaired. There he completed the equipment of his forces; selected the field-pieces and their carriages, balls and powder; and attended to the military accoutrements, stores and provisions.

On the 9th of May he passed over to Florida with four hundred selected men of his regiment, and a considerable party of Indians, headed by Molochi, son of Prim the late chief of the Creeks; Raven, war-chief of the Cherokees; and Toonahowi, nephew of Tomo Chichi. On the evening of the 10th, part of the Carolina forces arrived.

As the first thing to be done was to take the forts that kept open the communication of the Spaniards with the country, and thus cut off their supplies, the General, impatient of losing time, invested the small fort called Francis de Pupa, seventeen miles north of St. Augustine, commanded by a sergeant and twelve men, who surrendered without a contest. Thence he proceeded to Fort Diego, situated on the plains, twenty-five miles from St. Augustine, defended by eleven guns, and fifty regulars, besides Indians and negroes. In his sortie upon this, he made use of a little stratagem, as well as force; which was by appointing three or four drums to beat, at the same time, in different places in the woods, and a few men now and then to appear suddenly, and withdraw out of sight again. At this, the enemy in the fort were so confounded, with the apprehension that they were surrounded by a great number of troops, that they made only a feint of opposition; and, being summoned to surrender, did so, on condition of being treated as prisoners of war, and, (what they principally insisted on) not to be delivered into the hands of the Indians, from whom they were conscious that they had incurred the most condign reprisals for former aggressions. The other articles were that they should deliver up the guns and stores, which consisted of nine swivel and two carriage guns, with the powder and shot, &c.; that they should have liberty to keep their baggage; that Seignior Diego Spinosa, to whom the fort belonged, it having been built at his expense, and on his land, should hold his plantation and slaves, and such other effects as were not already plundered in the field; and, finally, that no deserters or runaways from Charlestown should have the benefit of this capitulation. Here he left a garrison of sixty men, under the command of Lieutenant Dunbar, to secure the retreat of the army, in case of accidents, and to preserve a safe communication with the settlements in Georgia. He then returned to the place of rendezvous, where he was joined on the 19th of May by Captain M’Intosh, with a company of Highlanders, and Colonel Vanderdussen, with the rest of the Carolina troops, but without any horse, pioneers, or negroes.

By this time six Spanish half-galleys, with a number of long brass nine pounders, manned with two hundred regulars, and attended by two sloops loaded with ammunition and provisions, had entered the harbor of St. Augustine, so that the forces in the town and castle were very nearly equal in numbers to the land forces brought against them, and their artillery much superior.

Notwithstanding all the reinforcement which Oglethorpe had received, it was judged impracticable to take the place by assault from the land side, unless an attack could be made at the same time by the boats of the men of war, and other small craft, on the sea side, on which the town had no intrenchments; and to begin a regular siege on the land side was impossible, as he had neither force enough for investing the place, nor any pioneers for breaking the ground, and carrying on the approaches. For this reason it was concerted between him and the sea commanders, that as soon as they arrived off the bar of the north channel, he should march up with his whole force, consisting of about two thousand men, to St. Augustine, and give notice by a signal agreed on, that he was ready to begin the attack by land; which should be answered by a counter signal from the fleet of their readiness to attack it by sea. Accordingly the General marched, and arrived near the intrenchments of St. Augustine, June 4th, at night, having in his way taken Fort Moosa, about three miles from St. Augustine, which the garrison had abandoned upon his approach. He ordered the gates of the fort to be burnt, and three breaches to be made in the walls.

As soon as it was proper to begin the attack, he made the signal agreed on, but had no countersign from the men of war. This was to his utter surprise and disappointment. The reason which was afterwards assigned, was, that the fleet had ascertained that their promised cooperation had been rendered impracticable; as the galleys had been drawn up abreast in the channel between the castle and the island, so that any boats which they should send in must have been exposed to the cannon and musketry of the galleys, as well as the batteries of the castle; and, as no ships of force could get in to protect them, they must have been defeated, if not wholly destroyed; and that it was impossible to make an attack by sea, while the galleys were in that position. It being presumptuous to make an attack without the aid of the fleet, the General was under the necessity of marching back to Fort Diego, where he had left all his provisions, camp furniture, and tools; because he had neither horses nor carriages for taking them along with him by land, nor had then any place for landing them near St. Augustine, had he sent them by water.

Disappointed in the project of taking the place by storm, he changed his plan of operations, and resolved, with the assistance of the ships of war, which were lying at anchor off the bar, to turn the siege into a blockade, and to shut up every channel by which provisions could be conveyed to the garrison. For this purpose, he stationed Colonel Palmer, with his company, at Fort Moosa, to scour the woods, and intercept all supplies from the country, and “enjoined it upon him, for greater safety, to encamp every night in a different place, and, by all means to avoid coming into action.” He also charged him, if he should perceive any superior party sallying forth from St. Augustine, to make a quick retreat towards Fort Diego, where it was certain the enemy would not follow him, for fear of having their retreat cut off by a detachment from the army. He sent Colonel Vanderdussen, with his regiment, to take possession of Point Quartell, at a creek which makes the mouth of the harbor opposite Anastasia; and this he did “because they would be safe there, being divided from St. Augustine, and covered from any sally that would be made by the garrison."

As there was a battery on Anastasia, which defended the entry to St. Augustine, the Commodore suggested that, if a body of troops should be sent to land upon that island, under favor of the men of war, and dispossess it, he would then send the small vessels into the harbor, which was too shallow to admit the ships. Upon this, the General marched to the coast, and embarked in the boats of the men of war, with a party of two hundred men, and most of the Indians. Captain Warren, with two hundred seamen, attached themselves to this expedition.

Perceiving that the Spaniards were advantageously posted behind the sand-hills, covered by the battery upon the island, and the fire from the half-galleys which lay in shoal water where the men of war could not come, he ordered the heavy boats to remain and seem as though they intended to land near them, while he, with Captain Warren and the pinnaces, rowed, with all the speed they could, to the southward about two miles. The Spaniards behind the sand-hills strove to prevent their landing, but before they could come up in any order, the boats had got so near to the shore that the General and Captain Warren, with the seamen and Indians, leaped into the water breast high, landed, and took possession of the sand-hills. The Spaniards retreated in the utmost confusion to the battery; but were pursued so vigorously, that they were driven into the water, and took shelter in the half-galleys.

All hands were now set to work to erect the batteries, whence a cannonade was made upon the town. This, however, was to little effect; partly from the distance, and partly from the condition of some of the field pieces which were employed. The enemy returned a brisk fire from the castle and from the half-galleys in the harbor. The latter, chiefly annoying the camp, it was agreed to attack them; but though Commodore Price had proposed that measure to Colonel Vanderdussen first, he altered his opinion and would not consent to it.

“Thirty-six pieces of cannon, together with planks for batteries, and all other necessaries, with four hundred pioneers were to have come from Carolina; but only twelve pieces of cannon arrived. Of course, for want of planks for batteries, they were obliged to fire upon the ground, the consequence of which was, that their carriages were soon broken, and could not be repaired."

The Spaniards, on the other hand, had surprised and cut to pieces the detachment under Colonel Palmer. Of this disastrous event, the particulars are given by one who could say, “Quos ego miserrimus vidi, et quorum pars magna fui.” [Which I had the misfortune to see, and greatly to share.] I refer to a letter from Ensign Hugh Mackay to his brother in Scotland, dated at Fort St. Andrews, on Cumberland Island, August 10th, 1740.

After some introductory remarks, he gives the following account of the action:

“On the 9th of June the General sent out a flying party of militia, Indians, and thirteen soldiers, in all making one hundred and thirty-seven men, under the command of Colonel Palmer, a Carolina gentleman, an old Indian warrior, of great personal resolution, but little conduct. Under him I commanded the party, and had orders to march from St. Diego, the head-quarters, to Moosa, three miles from St. Augustine, a small fort which the Spaniards had held, but was demolished a few days before; there to show ourselves to the Spaniards, and thereafter to keep moving from one place to another to divert their attention, while the General took another route, and intended to come to Moosa in five days. The orders were just, and might with safety be executed, had a regular officer commanded; but poor Colonel Palmer, whose misfortune it was to have a very mean opinion of his enemies, would by no means be prevailed upon to leave the old fort, but staid there, thinking the Spaniards durst not attack him. He was mistaken, as will appear presently.

“Upon the 15th day of June, about four in the morning, we were attacked by a detachment of five hundred, from the garrison of St. Augustine, composed of Spaniards, negroes, and Indians, besides a party of horse to line the paths, that none of us might escape. Apprehending that this would happen, I obtained leave of Colonel Palmer, and therefore ordered our drum to beat to arms at three o’clock every morning, and to have our men in readiness till it was clear day. Thus it was upon the fatal 15th of June, as I have said, when the Spaniards attacked us with a very smart fire from their small arms; in which Colonel Palmer fell the first. We returned the fire with the greatest briskness that can be imagined; and so the firing continued for some time; but, unluckily, we were penned up in a demolished fort; there was no room to extend. The Spaniards endeavored to get in at the ruinous gate; and our party defended the same with the utmost bravery. Here was a terrible slaughter on both sides; but the Spaniards, who were five times our number, got at last, by dint of strength, the better; which, when I saw, that some prisoners were made, I ordered as many of my party then as were alive to draw off. We had great difficulty to get clear, for the Spaniards surrounded the fort on all sides. However, by the assistance of God, we got our way made good; drew up in sight of the enemy, and retired, without being pursued, till we were in safety. I had no more than twenty-five men, and some of them very ill wounded, of which number I was, for I received three wounds at the fort gate, but they were slight ones. Several of the poor Highlanders, who were in the engagement, and fought like lions, lost their lives, some of them your acquaintance.

“I commanded, next Colonel Palmer, as captain of the horse, on the militia establishment. My lieutenant was killed. My cornet and quartermaster were made prisoners of war, with four more of the Highlanders. Charles Mackay, nephew to Captain Hugh Mackay, who was ensign of militia, received five wounds in the action, and lost one of his fingers; and, thereafter, rather than fall into the hands of the Spaniards, ventured to swim an inlet of the sea, about a mile broad, and had the good fortune to get to the side he intended, and so to the General’s camp.

“As the Indians fled several different ways, no more account is yet heard of them, only that some of them were killed in the action, and others wounded and taken prisoners. I believe there were sixty killed, and twenty taken prisoners of our whole party. To some of our Creek Indians who were taken by the enemy, leave was given (to curry favor with their nation) to return home. They told me that we killed a great number of the Spaniards at Moosa, and that they were dying by fives and sixes a day after getting into the town; so miserably were they cut by our broad swords; yet by their great numbers they got the day; but were sadly mauled, otherwise they would have pursued me.”

The fate of Colonel Palmer was the more affecting, from the consideration that he had raised one hundred and fifty good men, who had come with him as volunteers; that he was in a fort in which a breach had been made, and of course was no adequate protection; and that he was beyond the reach of any assistance. It has, indeed, been said that he was not enough mindful of the directions that had been given him, and presumptuously exposed himself to danger.

Mr. Stephens remarks that “the most bloody part of all fell to the unhappy share of our good people of Darien, who, almost to a man engaged, under the command of their leader, John Moore McIntosh; a worthy man, careful director among his people at home, and who now showed himself as valiant in the field of battle; where, calling on his countrymen and soldiers to follow his example, they made such havoc with their broadswords, as the Spaniards cannot easily forget." This brave champion was taken prisoner, and suffered severe and cruel treatment.

The principal commander of the Spaniards fell at the first onset.

The Spanish took several prisoners; basely insulted the bodies of the dead; and would have inflicted vengeful cruelties on their captives, one of whom was an Indian named Nicholausa, whom they delivered over to the Yamasees to burn, but General Oglethorpe sent a drum with a message to the Governor from the Indian chief of the Cherokees, acquainting him that if he permitted Nicholausa to be burnt, a Spanish horseman who had been taken prisoner should suffer the same fate. He also mentioned that, as the Governor was a gentleman and a man of honor, he was persuaded that he would put an end to the barbarous usage of that country; and expected from the humanity of a Spanish cavalier that he would prohibit insults to the bodies of the dead, and indignities to the prisoners; and he rather wished it, as he should be forced, against his inclination, to resort to retaliation, which his Excellency must know that he was very able to make, since his prisoners greatly exceeded those made by the Spaniards. Upon this the Governor submitted to the rescue of Nicholausa from the fate to which he had been destined. It was, also, agreed that the Indians, on both sides, should be treated as prisoners of war; so that an end was put to their barbarous custom of burning the unhappy wretches who fell into their hands.

Oglethorpe continued bombarding the castle and town until the regular troops came over from the land side, and the Carolina militia were removed from Point Quartel to Anastasia. He then summoned the Governor to surrender, but received an indignant refusal.

Soon after some sloops, with a reinforcement of men, and a further supply of military stores and provisions from Havana, found means to enter the harbor through the narrow channel of the Matanzas.

Upon this, all prospect of starving the enemy Was lost; and there remained only the chance of a forcible assault and battery.

As the dernier resort, it was agreed, on the 23d of June, that Captain Warren, with the boats from the men of war, the two sloops hired by General Oglethorpe, and the Carolina vessels, with their militia, should attack the half-galleys; and, at a given signal, the General should attack the trenches.

This was a desperate measure; for the whole of the troops belonging to the besiegers, including even the seamen, were much inferior in number to the garrison. The town was also covered on one side by a castle, with four bastions, and fifty pieces of cannon; from whence was run an intrenchment, flanked with several salient angles to Fort Coovo, on the river Sebastian. This intrenchment consisted of the neck of land from the river Anastasia to that of St. Sebastian, and entirely covered the town from the island.

Upon this the General drew in all the strength that he possibly could, and sent for the garrison that he had left at Diego. Being joined by them and by the Creek Indians, and having made a sufficient number of fascines and short ladders, provided all other necessaries for attacking the intrenchments, and brought up thirty-six cohorns, he received notice that the Commodore had resolved to forego the attack; declaring, that, as the season of hurricanes was approaching, he judged it imprudent to hazard his Majesty’s ships any longer on the coast.

On the departure of the fleet, the place was no longer blockaded on the sea side; of course the army began to despair of forcing the place to surrender. The provincials, under Colonel Vanderdussen, enfeebled by the heat of the climate, dispirited by fruitless efforts, and visited by sickness, marched away in large bodies. The General himself, laboring under a fever, and finding his men as well as himself worn out by fatigue, and rendered unfit for action, reluctantly abandoned the enterprise. On the fourth of July everything which he had on the island was reembarked, the troops transported to the continent, and the whole army began their march for Georgia; the Carolina regiment first, and the General with his troops in the rear. On this occasion a very notable answer of the Indian Chief is reported; for, being asked by some of the garrison to march off with them, “No!” said he, “I will not stir a foot till I see every man belonging to me marched off before me; for I have always been the first in advancing towards an enemy, and the last in retreating."

“Thus ended the expedition against St. Augustine, to the great disappointment of both Georgia and Carolina. Many reflections were afterwards thrown out against General Oglethorpe for his conduct during the whole enterprise. He, on the other hand, declared that he had no confidence in the Provincials, for that they refused to obey his orders, and abandoned the camp, and returned home in large numbers, and that the assistance from the fleet failed him in the utmost emergency. To which we may add, the place was so strongly fortified both by nature and art, that probably the attempt must have failed though it had been conducted by the ablest officer, and executed by the best disciplined troops."

The difficulties which opposed his success, showed the courage that could meet, and the zeal that strove to surmount them; and, while we lament the failure, we perceive that it was owing to untoward circumstances which he could not have foreseen; and disappointments from a quarter whence he most confidently expected and depended upon continued cooperation and ultimate accomplishment. Referring to this, in a speech in the British house of Peers, the Duke of Argyle made these remarks: “One man there is, my Lords, whose natural generosity, contempt of danger, and regard for the public, prompted him to obviate the designs of the Spaniards, and to attack them in their own territories; a man, whom by long acquaintance I can confidently affirm to have been equal to his undertaking, and to have learned the art of war by a regular education, who yet miscarried in the design only for want of supplies necessary to a possibility of success."

A writer, who had good authority for his opinion, declares, that,” though this expedition was not attended with the success some expected from it, the taking the fortress of St. Augustine, it was, nevertheless, of no little consequence, inasmuch as it kept the Spaniards for a long time on the defensive, and the war at a distance; so that the inhabitants of Carolina felt none of its effects as a Colony, excepting the loss suffered by their privateers, till the Spaniards executed their long projected invasion in 1742, in which they employed their whole strength, and from which they expected to have changed the whole face of the Continent of North America; and, even then, the people of Carolina suffered only by their fears."

In a letter to Lord Egmont, by Governor Belcher, dated Boston, May 24th, 1741, is this remark; “I was heartily sorry for the miscarriage of General Oglethorpe’s attempt on Augustine, in which I could not learn where the mistake was, or to what it was owing, unless to a wrong judgment of the strength of the place, to which the force that attacked it, they say, was by no means equal. I wish that a part of Admiral Vernon’s fleet and General Wentworth’s forces may give it a visit, before the Spaniards sue for peace. It seems to me absolutely necessary for the quieting of the English possessions of Carolina and Georgia, that we should reduce Augustine to the obedience of the British crown, and keep it, as Gibraltar and Mahon."