Henry Strangways (died 1562), also sometimes known as Strangwish,[2] was an English "Gentleman Pirate"[2] who attacked Spanish and other shipping.

[5] 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".

[4] There he joined forces with the Cornish Killigrews, successful pirates themselves, using Portland Castle as a den to store loot.

[7] 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.

[3] 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.