Capt. Robert Searle's Raid of 1668
ln 1668, the Spanish presidio of
San Agustin (
At about 1:00 on the morning of May 29th, over 100 pirates slipped into small
boats and began rowing stealthily across the bay. Corporal Miguel de Monzon was
fishing in his dugout canoe and heard the sound of oars pulling across the
water. As he began rowing toward the town wharf to sound the alarm, the corsairs
raced after him and shot him twice as he reached the shore. Despite his wounds,
Monzon began shouting a belated warning and managed to reach the safety of the
city's decaying wooden fortress. Behind him, the buccaneers stormed ashore.
The townspeople of San Agustin were caught completely by surprise. Bands of
freebooters scattered through the streets, seizing or shooting the frightened,
half-naked inhabitants as they emerged from their houses. Sergeant Major Nicolas
Ponce de Leon the Younger, senior officer of the presidio’s garrison, rushed to
the guardhouse to find it already pillaged and deserted. As the pirates gathered
at the fort to storm it, he shepherded 130 bewildered men, women, and children -
including 70 unarmed soldiers - to safety in the woods a league away.
The raiders crossed the north end of the city's plaza to Government House, the
seat of local authority and residence of the royal governor. Governor Francisco
de la Guerra y de la Vega saw the buccaneers approaching and knew he had to get
to the fort and direct its defense, one of his primary duties as governor. He
escaped through a hidden door and, with the freebooters on his heels, safely
reached the stockade with several other refugees.
Adjunt lsidro de Reinoso, sentry duty at the fortress that night , was making
his rounds when he heard the tumult caused by the buccaneer's landing. He
notified the lieutenant of the fort, Captain Mateo Pacheco Salgado, who
immediately alerted the troops on duty. The stockade's gate opened to admit the
town guard from the guardhouse, the governor and other royal officials, and a
handful of additional men. Governor de la Guerra y de la Vega took command of
the 33 men within the stockade's dilapidated wooden walls and ordered the powder
magazine to be opened and ammunition distributed to the soldiers present.
Before its cannons could be loaded, Searle's crew attacked the fortress. For an
hour and a half, the corsairs repeatedly tried to storm the walls, only to be
driven back by heavy musket fire. Firing at the glowing matchcord carried by
each Spanish musketeer, the brigands were able to kill five of the defenders and
wound five more. The buccaneers finally withdrew, with 11 men dead and 19
wounded. By failing to watch the stockade closely after their repulse, the
pirates allowed Governor de la Guerra y de la Vega to improve his defenses.
Messengers were secretly sent to urge every soldier they could find to report to
the fort. By daybreak on May 29"', seven soldiers had arrived. Major Ponce and
his 70 weaponless men soon followed them. Also with daylight came another vessel
– Searle’s own craft, the 60ton/8 gun Cagway ,joining the two ships already
anchored in
The corsairs on shore returned to the unfinished task of systematically sacking
San Agustin. The king's treasury yielded 138silver marks, which had been
salvaged in 1667 from the Nuestra Senora de las Maravillas, a galleon which sank
in the Bahama channel in 1656. The royal warehouses were robbed and the hospital
pillaged. The parish church and the Franciscan convent chapels were stripped of
their ornaments. Homes were carefully searched for jewels and other valuables.
The booty was loaded aboard the Cagway and the ship from
As the looting drew to an end, the pirates seized hostages—the royal treasurer,
Jose de Prado, who had refused to abandon his house, and some local natives and
mestizos (persons of mixed Spanish and native American stock.) On the afternoon
of May 29th , Governor de la Guerre y de la Vega rallied his forces and sent a
sortie from the fort to drive the marauders from the city. He detailed artillery
Captain Nicolas Esteves de Carmenatis to command two parties of 25 men each
(under the Adjunt Francisco Ruiz Canizares y Osorio and Ensign Diedo Diaz Mejia)
and execute the operation. Between 3PM and 4PM, Esteves sallied from the
stockade, unaware that only 40 buccaneers were still ashore. The soldiers went
reluctantly, displaying little military experience and less enthusiasm. After
they had received fire from the raiders, wounding both Canizares and Diaz, the
governor recalled the troops “so that the enemy would not kill them as if they
were sheep.”
At about nine o'clock that evening, the last 30 pirates who remained ashore
rowed back to their Ships. The sack of san Agustin had lasted 20 hours. Behind
them, the buccaneers left a grief stricken people—60 of their relatives and
friends were dead. Yet with the tears came prayers of thanksgiving, for the
freebooters did not set sail immediately, carrying off their hostages. On May
30th, Capt. Searle sent Governor de la Guerra y de la Vega a message, offering
to ransom his captives—about 70 men, women, and children—in exchange for water,
meat, and Wood.
The governor accepted, but in return asked for some much-needed flour from the
Verscruz ship, as well as the prisoners, The same day, as a good gesture of good
faith, the women—their honor intact—were released before the other captives.
Over the next six days, the ransom was paid. on June 5th , the treasurer, the
priest, the crews of the
The sack of San Agustin was, however, a blessing in disguise, for it shocked the
ponderous bureaucracy into action. Mariana, Queen regent of
She ordered the Viceroy, Don Antonio Sebastian de Toledo Molina y Salazar to
support a full 300-man garrison in
