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The portrait was painted in the year Sydney was recalled from Ireland as Lieutenant General of the Horse, and shortly before commencing governership of Dover Castle in October 1648. His link with the Master I.W. may have been a family one. I.W. was a Leicestershire based artist, and therefore probably known to the family of the Earl of Leicester.

A Republican and ''patriot'', Algernon Sydney was the son of the second Earl of Leicester and grandson of Sir Philip Sydney. He fought on the Parliament side in the Civil War, but he disapproved of the execution of Charles I. Nevertheless, he played an important part under the Commonwealth until 1653 when the Republican faction was eclipsed. In 1659 he returned briefly to public life, but went abroad from 1660 to 1667. He took part in the various plottings against Charles in 1682-3, and was executed in 1683 for the part he played in the Rye House conspiracy and for writing against Sir Robert Filmer. This work was published in 1698 as his ''Discourses Concerning Government''. Sydney was impatient, overbearing and irascible, ''of rough and boisterous temper'', but his defiance of tyranny gave him a great reputation with posterity.