The artist intended this painting to commemorate a 'very gallant action in the West Indies' on 1 October 1807. At dawn, off the coast of Barbados, a lookout aboard the 'Windsor Castle', mail packet, saw the sail of a French privateer the 'Jeune Richard', overhauling them. With no prospect of escape the crew of the 'Windsor Castle' rigged the anti-boarding nets and went to quarters. The privateer closed on her starboard quarter and grappled but the nets prevented the Frenchmen from boarding. Both sides suffered severely from the fire of the guns and muskets, especially the French who finally ran from their quarters. Seeing this, Captain William Rogers and his remaining five unwounded men boarded the Frenchman, killing her captain, tearing down her colours and forcing the crew to go below.

The powerful French privateer had a crew of 92, an armament of six long 6-pounders and an 18-pounder mounted on a swivel carriage set in the middle of her waist. The 'Windsor Castle' only had a crew of 28 and an armament of six 4-pounders and two 6-pounders, so their action reflected great credit on them.

The scene is viewed from the 'Jeune Richard's' starboard main shrouds. In the centre of the painting Captain Rogers has boarded the privateer with his five remaining men and stands on the deck preparing to shoot the boatswain. Behind him a sailor aims a musket and another swings the butt of a pistol. Above them in the port main shrouds, another sailor attacks two Frenchmen overhead with a sword. The forecastle of the 'Windsor Castle' is in the background, with three sailors attacking the French with pistols to the right. As Rogers steps on to the swivel of the 18-pounder, a Frenchman falls on his right but another, wounded in the foreground and with his back to us, points a pistol at him. A dead Frenchman lies on the right.

Drummond painted this picture using his own a head-and-shoulders portrait of Rogers from life as a basis (see BHC2972). He is shown striking a dramatic, determined pose, his right arm thrust forward while behind him a vortex of smoke, men and thrusting weaponry accentuates his bravery against the odds. This painting was exhibited at the Royal Academy in 1808 and the picture was also engraved in mezzotint by W. Ward in 1809.