A three-quarter length portrait turned to the right. Whetstone stands with his back to rocks on his left. He wears a brown velvet coat with gold buttons and a dark brown full bottom wig. His left hand rests on a baton and with his right he gestures towards two warships behind him on the right. One of the ships wears his flag as Rear-Admiral of the White.

As a junior captain from 1689-91, he convoyed supplies to Ireland for two years. In 1702 he joined Vice-Admiral John Benbow in the West Indies and remained in charge at Jamaica when Benbow sought out a small French squadron expected in the area. When the squadron returned to Port Royal, Whetstone was president of the courts martial which tried the several captains who had conspired against their admiral. He succeeded to the command when Benbow died of his wounds. Prince George promoted him to rear-admiral over the heads of senior captains and he was sent out to the West Indies as Commander-in-Chief in 1705. However his squadron was too weak to be effective against the Spanish fleet. In 1707 he was ordered to convoy some merchantmen bound for the White Sea as far as the Shetland Islands. The enemy squadron he was to protect them against was commanded by the redoubtable corsair le Comte de Forbin. Whetstone exceeded his instructions and continued to convoy the merchantmen well past the Shetlands, but two days after he left them Forbin intercepted the convoy and took 15 ships. Though not to blame, Whetstone was made the scapegoat for this misfortune, and not employed again. The portrait was probably painted in 1707 and was presented to the Greenwich Hospital Collection by George IV in 1824.