Henry Strangways

Henry Strangways (died 1562), also sometimes known as Strangwish, was an English "Gentleman Pirate"

Strangwish is the nephew of Richard Manners, husband of Margaret Dymoke. Richard is the brother of Margaret Manners, both are children of George Manners, '11th Baron de Ros', of Helmsley and Anne St Leger, daughter of Anne of York, Duchess of Exeter, the daughter of Richard Plantagenet, 3rd Duke of York and Cecily Neville.

Margaret is mother of Strangwish, his father is Sir Henry Strangewish, thus he is sometimes referred to as a "Gentleman Pirate". However, piracy seems to have taken precedence, he attacked not a Spanish island but Spanish ships. This is known to us because of an official complaint and request for damages which was made out to Philip II of Spain in which a ship, belonging to Johannes de Bagnes, was plundered by Enrriex Tranquaz (i.e. Strangways). The demand was made via Basilio Pignatelli, the Bishop of L'Aquila in 1559. Strangway's imprisonment in December 1560 is probably related to his Spanish piracy; but he was released, this time under a promise of good conduct, further suggesting he had powerful friends and/or served a political state purpose behind his activities. The Royal Pardon after his death, the many releases from jail, and the seemingly complicit co-operation by authorities (the use of Portland Castle as a pirate den for instance), has suggested to later historians that Strangways' reputation is as much a "privateer" as pirate.

Portrait During one of Strangways' imprisonments in 1554 he became friends with fellow prisoner Gerlach Flicke. Flicke, who had been working as a portrait painter in England for about ten years (although born in the German town of Osnabrück), painted a double portrait of Strangways and Flicke while in prison. Why Flicke was imprisoned is not known but Strangways was known to have been imprisoned for his piracy.

The double portrait of Strangways, with lute in hand, and Flicke, carrying his artist's palette, is in the National Portrait Gallery in London. The portraits are both miniatures, being less than high. The self-portrait has a Latin inscription that may be translated, Such was the face of Gerlach Flicke when he was a painter in the City of London. This, he himself painted from a looking glass for his dear friends. So that they might have something to remember him after his death. Although the two portraits are on the same piece of material, Flicke's inscription is in Latin, whilst Strangways' is in English and reads, Strangwish, thus strangely depicted is One prisoner, for thother, hath done this/ Gerlin, hath garnisht, for his delight This woorck whiche you se, before youre sight.