Admiral Sir William Sidney Smith, the British naval officer pictured here, forged a reputation as a war hero who excelled at combining land and sea operations. He is well known for breaking Napoleon’s siege of Acre in what is now Israel during the French Revolutionary Wars. However, the same impulsiveness and energy that perhaps made Smith successful in war later damaged his reputation. His character might have been chivalrous and brave, but his unconventional ways sparked fear and distrust. Sir Henry Raeburn, the painter of this portrait, typically set his canvas beside or behind his subject and then made conversation until he witnessed the desired expression. Raeburn then moved to the canvas and recorded the picture in his mind as quickly as possible.