Sir John Bolle at Cadiz

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See also The Bolles of Haugh Family Tree and Sir John Bolle in Ireland

In 1596 Robert Devereux, the 2nd Earl of Essex was placed in command of an Anglo-Dutch army which sailed in a fleet commanded by the Earl of Nottingham, Charles Howard, to attack the important Spanish trade and military city of Cadiz.  The officers involved are listed by Sir Francis Bacon as:  Lord Charles Howard, Lord Admiral; The Earl of Essex and the Lord Admiral to be both Generals by sea and land; Lord Thomas Howard, Vice-Admiral; Sir Francis Vere, Lord Marshall and Sir Walter Raleigh, Admiral.   Bacon’s lists the Earl of Essex’s regiment’s Captains as Alderish, Savage, Morgan, Carew, Lambert, Grant, Higham and Goring.  The Colonels, Majors and Captains of all the other regiments are then listed but there is no mention of John Bolles in the list.  The list includes 100,000 unnamed foot and ‘a number of horsemen’.  Being from a wealthy family Bolles would likely have been one of the mounted horsemen but wasn’t yet of enough significance to be listed amongst the senior officers.   At age 26 and from a noble house, while not yet a Captain he was likely to have been a Lieutenant but that was about to change.

Upon arrival, the Anglo-Dutch fleet found a Spanish fleet unprotected in the harbor.  Rather than having them captured, the Spanish set fire to their own ships.   They then landed their troops who captured, sacked and burned the city.  The horsemen were landed first and led a powerful attack against the Spanish horsemen who had come out to meet them.  Their attack was so furious that they overran the Spanish and were able to charge right through the gates into the city where they led the attack followed by the footmen to quickly seize the city.  After looting and burning much of the city they decided they would not be able to hold it once the Spanish Fleet arrived so they departed taking many of the city’s prominent citizens back to England for their ransom.  John Bolle must have so distinguished himself in the battle that he came to Essex's attention.  He was one of only 64 men whom Essex took it upon himself to knight on the battlefield.  ref book  Queen Elizabeth would later count that as one of Essex's offences when he later came into disfavour with her but she allowed the titles to stand.

Sir John Bolles had the custody of a young lady of high position who then fell in love with him.  Her tragedy at learning of his loyalty to his wife has been told in Percy’s ‘Reliques’ as ‘The Spanish Lady’s Love For An Englishman’ which is known colloquially as The Story of the Green Lady.

The battle was a huge success for the English.  The loss of 32 ships which had been fully laden with supplies to sail in a great fleet for the Spanish colonies in the New World contributed to the bankruptcy of Spain’s royal treasury that year.  After this success the 2nd Earl of Essex, Robert Devereux, was given the post of Lord Lieutenant of Ireland charged with ending the rebellion there.  That same year he led the largest expeditionary force ever sent to Ireland - 16,000 troops including Sir John Bolle - with orders to end the rebellion. 

See Sir John Bolle in Ireland for the continuation of this history