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"Second Battle of San Juan (1598)" Topic

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HarryHotspurEsq13 Aug 2009 7:57 p.m. PST

A while back I saw that Cacique Caribe posted some information on English attempts to take Puerto Rico from the Spanish. He was interested in the first attempt led by Sir Francis Drake in 1595, but I am after info on the second attack.


Second Battle of San Juan
June 16-18, 1598

Sir George Clifford, 3rd Earl of Cumberland (English) leading a force brought in 20 ships.
Governor Pedro Suárez Coronel (Spanish) leading the garrison and colonial militia.

Clifford, observing Drake's failed seaward attack in 1595, lands his forces to the east of San Juan and attacks the city from the landward side. He is held up by a gun battery at Boquerón but ultimately seizes the town and besieges the remaining Spanish forces at El Morro. These surrender due to sickness on the 1st of July. However, Clifford only holds the settlement for 65 days. Due to a violent outbreak of dysentery his numbers were reduced to a point that he could no longer defend his position if attacked and he withdrew.

I'd like to replay Sir George Clifford's attack in 15mm and am looking for any extra information, maps etc. I have given up hoping that there might be a reliable order of battle though… An advanced and hopeful 'thanks' to all and sundry.

Personal logo Cacique Caribe Supporting Member of TMP13 Aug 2009 8:34 p.m. PST


Glad to see you working on it. Yes. It was me, for the 1595 attack:

TMP link

First, there doesn't seem to have been much in 1595-1598, other than El Morro on the tip (construction started 1539), and La Fortaleza (construction started 1533 – #2 on map):


Two hundred years later (1797), the city walls were up and San Cristobal (built starting 1634) was in place to guard entrance from land:


"El Morro Captured
Merely three years after Drake's attack, the English returned, led by Sir George Clifford, the Third Earl of Cumberland. It was this attack that proved to be the only one to ever break through and capture El Morro.
'The first attack was with Drake, [and it] was from the front and was unsuccessful,' said Almodóvar.
'But after the first attack, the enemy tried from the back, because they learned the lesson there.'
In addition to Cumberland realizing the advantage of a land attack, the troops that had been present from Drake's attack were now non-existent after having only been brought to protect a treasure ship that had been forced to dock at San Juan. This left the city with around only 300 troops, including volunteers, a number that dropped over the years due to famine and disease to around 150.
By the time Cumberland arrived from the east end of San Juan, he and his 1,700 men found the land bridge ill-protected, and Spanish deserters were quick to point out how to take El Morro by siege and how to prevent supplies from reaching the fort's around 80 defenders.
This victory would be short-lived, however, as the same dysentery that had crippled the Spanish troops spread to Cumberland's men, incapacitating 400 of them and killing another 400. They left just a few weeks after taking El Morro, but pillaged and destroyed the city just before their departure.
In the wake of the attack, Spain sent more soldiers, supplies and weapons to rebuild the city and its defenses. From 1601 to 1609, the reconstruction of El Morro saw its toppled hornwork strengthened with the foundations still used today. A small fort now known as El Cañuelo was built at the opposite end of the San Juan Harbor entrance in order to work in tandem with El Morro's guns to create crossfire to deter invading enemy ships."

PS. Do you read Spanish?

Personal logo Cacique Caribe Supporting Member of TMP13 Aug 2009 9:12 p.m. PST

I'm trying to find where Gobernador Suarez fits into the chronology:


He seems to have served from 1593-1597, during Drake's attack (1595), but apparently not during Cumberland's (1598).

This seems to indicate that Suarez served on two occasions:



Personal logo Cacique Caribe Supporting Member of TMP13 Aug 2009 9:19 p.m. PST

Gobernador (Captain General) Antonio de Mosquera was in charge in 1598:

"With a desire for vengeance and embarrassed by the defeat suffered by Sir Francis Drake in 1595, the English Crown sent out a new expedition under the command of Sir George Clifford, Duke of Cumberland, assisted by Sir John Berkeley. The primary aim was to capture Brazil, which was then part of the Spanish Empire. However, according to some historians, England�s true intent was always to take Puerto Rico, known as the "Key to the Indies", and to add it to its empire.
After the attack by Drake, San Juan was left with a garrison of 200 men, together with some 150 volunteers. The five ships returned from Spain, bringing 200 soldiers for the new Governor, Antonio de Mosquera. Dysentery had laid many men low and there was so little food that the island was on the point of famine. Cassava bread and plantains were the only food they had. As a result of this combination of hunger and poverty, many soldiers had lost their military discipline and had become thieves.
On June 16, 1598, the English fleet appeared unexpectedly off the coast of the island. Clifford disembarked in El Condado and tried to get to San Juan, but the Spanish had burnt the water bridge and retreated to the bastion of Boquer�n. Clifford almost drowned trying to cross the San Antonio channel, but was rescued by his men. They retreated with mounting casualties.
They attacked again on June 18 but by this time, the Spanish had retreated and taken refuge in the Castle of El Morro. During the next ten days the English fired only a few shots at the Castle, but they were well aware that the Spanish were suffering an epidemic of dysentery and were also short of food and munitions. Although they wanted to take the Castle, they had no intention of destroying it. On June 29, Clifford allowed the Spanish commander and his troops to leave El Morro and offered to transport them to Cartagena, but in actual fact he took them to Jamaica instead. The English sacked the city of San Juan but the dysentery epidemic attacked them also, killing hundreds, and for this reason, Clifford departed."

"The best commentary upon Drake s attempts and fail
ures is, perhaps, the narrative of the Earl of Cumberland s
more successful attack upon the same place a few years
George Clifford, Earl of Cumberland, was one of those
distinguished adventurers of the Elizabethan era, who,
though not without hope and desire for gain, seems to
have been actuated quite as much from a chivalrous love
of adventure as from any other motive. His social posi
tion and ample personal wealth gave him a standing which
enabled him to introduce good order and discipline among
his followers in the various enterprises initiated by him,
and caused his attack upon San Juan to be considered
then and now, " as a fine, orderly operation of war con
ducted with no less humanity than gallantry."
The expedition with which we are now concerned was
the tenth and last that the Earl of Cumberland had
formed, and was accompanied by the earl in person, as
admiral and commander-in-chief. Sailing from England
on the 6th of March, 1598, with a force of twenty vessels
of all sorts, he had for his flagship the famous " Scourge
of Malice," christened by Queen Elizabeth herself, and
ranking, with its eight hundred tons, among the very first
vessels of the day. His second in command, styled
" Lieutenant-General and Vice- Admiral," Sir John Ber
keley, carried his flag on the " Merchant Royal." As a
whole, his force was more formidable, it was said, than
any that had heretofore been assembled by a subject of
the kingdom.
Arriving at the Canaries, Cumberland took and plun
dered the island of Lanzarote, and then pushed across for
the West Indies, arriving at the island of Dominica on
the 23d of May. Leaving there on the 1st of June, the
expedition proceeded to the Virgin Islands, where the
landing-parties were organized and drilled.
Leaving the Virgin group, the fleet made the eastern
end of Puerto Rico, and coasted along the north shore of
the island until the vicinity of San Juan was reached.
The sea being calm, a force of about one thousand men
was landed on the beach to the eastward of the town and
island of San Juan, observed only by a small group of
Spanish horsemen.
A day s march, after landing, brought the English to
the inlet already spoken of as the Boqueron, and to a
halt, as boats were wanting to cross to the island. At
this time, the defences of San Juan were much the same
as at the time of the previous attack ; but the garrison
which Drake encountered and Tello commanded was
stronger than the one which Cumberland had to deal with.
By the disappearance of the Spanish horse, Cumberland
was led to suspect another approach to the town ; and
through the aid of a negro guide discovered the cause
way which connected the southeast end of the island of
San Antonio with the mainland which was covered then,
as now, by the small fort at San Antonio. Cumberland
gave his men a few hours rest after darkness had set in,
and they all slept in their armor on the bare ground.
Before daybreak, the attack was made under the leader
ship of Sir John Berkeley. The causeway was rough,
and the Spaniards were upon the alert, and opened such a
hot fire that the English were compelled to withdraw at
daylight, with a loss of fifty men.
It was on account of the persistent requests of his
subordinates, that the Earl of Cumberland had resigned
the leadership of this assault to his second in command ;
but history tells of his part in the matter. He could not
keep out of the fight, and stumbling along the causeway
in the dark, he was thrown off his feet, and pushed by
accident into the shoal water. Falling on his back, and
encumbered with his armor, he could not get up, and
would have been drowned had he not been fished up,
after some delay, by two of his men. When finally
rescued, he had swallowed so much salt water as to be
very sick, and was obliged, most unheroically, to spend
the remainder of the night, in a state of complete exhaus
tion, sitting by the side of the causeway.
The next attack was made upon the fort at the Boque-
ron, now known as San Geronimo, by the combined force.
One of the vessels of the fleet was brought close under
the guns of this fort. To do this she had to be grounded
in front of the fort; but the sacrifice of the ship was
thought to be justified by the results, and the fort was
reduced to ruins. The assaulting party effected a landing
across the Boqueron, and after a march of a mile (the
town was smaller in those days) the town was reached,
and found to be deserted by all of the population capable
of bearing arms, who had repaired to the Morro. This
castle was finally taken, and, with the town and the rest
of the defences, came into possession of the English.
It was Cumberland s original intention to retain pos
session of San Juan as an English colony ; but climatic
diseases, principally of the nature of yellow fever, so
reduced his command that he returned to England, leav
ing Sir John Berkeley in charge ; and then Berkeley
followed, joining his admiral while still upon his home
ward route."

LOTS more here:



In Spanish here:



HarryHotspurEsq13 Aug 2009 10:46 p.m. PST

Wow. Good stuff! But no, unfortunately Spanish is not one of my many, many, skills…

I think you're right about Antonio de Mosquera being the Captain General at the time of Clifford's attack, although resistance during and after the English occupation of San Juan seems to have been organised by the previous governor, Pedro Suárez Coronel, who subsiquently went on to govern again. I guess it makes sense if de Mosquera was killed during the attack or surrendered and was relocated by Clifford to Jamaica, the next most senior Spaniard on Puerto Rico would take over.

According to your different sources there, it seems that Clifford landed anywhere from 700 to 1,700 men for the attack. The Spanish only 300 or so defenders. The primary evidence seems to be dominated by Spanish accounts and I wonder how much poetic license they took with numbers?

Now I just have to work out ideas for terrain…

Thanks a lot for all that great info!

The Jim Jones Cocktail Hour Inactive Member14 Aug 2009 2:35 a.m. PST

I took a tour around Valparaiso in late Feb and the guide had the bloody cheek to describe Drake as a pirate. Then again she owed me one, in answer to her question about what was notable in Vina del Mar I did answer that it was where the fascists planned their coup.

Might think about doing Drake raiding Chile, that sounds like fun.

Oh Bugger Inactive Member14 Aug 2009 5:20 a.m. PST

'the guide had the bloody cheek to describe Drake as a pirate.' When it comes down to it he was.

HarryHotspurEsq14 Aug 2009 5:26 a.m. PST

Nah, a privateer. There is a legal distinction in that Drake et al. were commissioned to to annoy the Spanish. Real pirates do it for fun.

pilum40 Supporting Member of TMP19 Aug 2009 3:33 a.m. PST

I like the Errol Flynn movie

HarryHotspurEsq21 Aug 2009 1:31 a.m. PST

Well during the week we played two more battles of Irregular Wars link , one a historic scenario, and the other a random engagement.

The first game was based on the capture of San Juan de Puerto Rico by Sir George Clifford in 1598. The part of the campaign we played was the assault on the artillery emplacement at El Boqueron on June 18.

The Spanish under Captain-General Antonio de Mosquero were deployed on and around the heights of El Boqueron with their saker deployed at the very top. They also received two companies of militia pike, one each of militia shot and conquistadors, and a priest to help boost their morale. de Mosquero led the conquistadors personally. Clifford had the numerical superiority, leading a company of like-minded gentlemen adventurers, he was followed by four companies of volunteers, two companies of halberdiers, one company of ships guns and a company of Cimeroons which he picked up during the march.

The first few turns saw the English marching inexorably forward into position below the hill. Although the Spanish shuffled their lines a little and de Mosquero pranced his conquistadors around like Lipazzana dancing ponies, by the end of turn four they were all still on the hill. Poor rolling by both sides saw little damage caused by either gun battery.

Going into turn five, the English numbers began to tell with a massive volley of shot from the gentlemen, volunteers, and Cimeroons which saw the first real loss or resolve among the defenders. de Mosquero threw himself into combat against the Cimeroons on the English flank and in the English turn the volunteers and halberdiers swept up the hill. With their lord in combat (and doing well), only the Spanish priest was available to try to rally the Spanish line. Unfortunatley for him, the English just proved too many and as the first Spanish company (the shot) scattered into the woods and off the board, the priest took fright and followed. With the shot and their padre scattering before them, the crew of the saker lost their resolve and turned tale as well. This was all too much for the pike militia (after all they were only there to defend the guns!) and with the enemy to their front and flanks, both fled. de Mosquero and his conquistadors, although quite successful to this point, saw their entire battle route before them and considered discretion to be the better part of valour.

All in all, a bit of a walk over really for the English – but a historical result none-the-less.

We then played a random match up between a battle of Royal English and one of Antrim Scots (a newly developed nationality). The English rolled well for recruitment, ending up with a company of demi-lancers led by the lord, two militia pike companies, a volunteer pike company, two companies of halberdiers and six companies of Irish kern. Foolishly, the English forgot to recruit anyone with a gun. The poor old Scots only scraped together a single company of gallowglasses to guard their lord, three companies of Islesmen targeteers and a salvaged Armada cannon.

Seeing there chances of a good fair fight slipping away, the Scots found the highest hill they could behind the muckiest swamp and decided to sit on the defensive. One more, the English advanced the length of the field to end up below a hill. Apparently when the Scots salvaged their ship's gun, they let the Spanish gunners drown because for the life of them they couldn't get the damn thing to have effective fire. Unlike the battle of San Juan though, in this instance the bog slowed the English pikemen down to only a 1" movement. The kern ran on through it as though they'd been doing it all their life… however this resulted in the kern getting a few inches ahead of the pike line. At this time the Scots saw their opportunity.

Seizing the opportunity the Islesmen threw themselves down the hill onto the two most advanced companies of kern and quickly made them scatter. That was all it took to force the remaining four companies of kern to route, avalanching lost resolve onto the main English line. Seeing their Irish allies run, the English soon followed them and the Scots were left as the very unexpected victors of the day.

Lessons learned: aside from a couple of other tweaks to the army lists, we have decided that some melee oriented company types need to have more resolve! Although there is nothing that can be done about fleeing friendlies looking like they want you to join them, we will be playing out pike, halberdier etc companies with a bit more…. 'resolve'. All in all, they were fun, fast games and we look forward to more.

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