Having escaped from British blockaders off Boston on December 18, 1814, the ship and her veteran crew had spent the last two months cruising Atlantic sea lanes in search of prizes. While they’d made a few captures, they still had yet to fall in with a real prize- a British convoy bound to or from the West Indies and the Mediterranean.
Steering southwest from Portugal, by February 20 they were about 60 leagues (180 nautical miles) east northeast of the island of Madeira. The light northeast breeze failed to dissipate the slight haze hanging over the water, but at 1 PM the masthead lookout distinguished a large ship sailing to the southwest. A half an hour later he spotted another further to the westward. Anxious to discover their true character and to prevent their joining company, Constitution’s crew raced aloft to set every sail, and the chase was on.
|Captain Charles Stewart as he appeared at the time of the battle, from an engraving in the Analectic Magazine and Naval Chronicle, 1816. USS Constitution Museum collection.|
Although the Americans did not know it yet, the two ships were HMS Levant, a 21-gun sloop-of-war under the command of the Honorable George Douglas, and HMS Cyane, a 34-gun frigate commanded by Gordon Falcon. The British knew Constitution might intercept a convoy that had just sailed from Gibraltar, and they were determined to capture or disable the American ship to prevent that from happening.
Captain Stewart sat astride the hammock nettings directing the action, seemingly immune to British shot. Constitution’s forward guns played upon the Levant, while the after most guns took aim at Cyane. In an attempt to close the range (to maximize the hitting power of his carronades), Cyane's Captain Falcon spilled the wind from his maintopsail, and allowed Constitution to forge ahead. He put the helm down and tried to edge up onto the American’s lee quarter. Perceiving the danger, Stewart fired a broadside into Levant, ordered Constitution’s mizzen topsail backed, and “closed with the sternmost ship under the cover of the smoke”- a demonstration of supremely fine ship handing!
In this contemporary oil-on-panel painting by Ambroise Louis Garneray, Constitution has just backed down to engage Cyane more closely. USS Constitution Museum collection.
It took little more than an hour to send a prize crew on board the Cyane and secure the prisoners. At 8 PM, Constitution made sail for the Levant, still in sight to leeward. Gallantly, the British turned to face their opponents. Just before 9 o’clock the two ships passed broadside to broadside on opposite tacks, like knights at a joust. Stewart immediately tacked Constitution across Levant’s stern and delivered a decisive broadside. Captain Douglas knew his only chance of survival was to set all the sail the masts could bear and try to escape from her overpowering enemy. Although the British had a slight lead, Constitution’s sails were in far better condition, and by 10 PM the Americans closed on the wounded ship. Captain Douglas struck his colors with reluctance. 
Constitution received little damaged in the engagement, and by 1 AM, the ship was ready to fight another battle. Cyane and Levant, however, suffered considerably. According to American Midshipman Pardon Mawney Whipple, “the decks of both vessels were literally covered with dead & wounded.” As part of the prize crew, he spent the next three days on board the Levant:
[T]his being the first action I was ever in, you can imagine to yourself what were my feelings to hear the horrid groans of the wounded & dying, & the scene that presented itself the next morning at daylight … the quarter deck seemed to have the appearance of a slaughter house, the wheel having been carried away by a shot – killed & wounded all around it, the mizenmast for several feet was covered with brains & blood; pieces of bones, fingers, & large pieces of flesh were picked up from off the deck [.] T’was a long time before I could familiarize myself to these & if possible more horrible scenes that I witnessed. 
Despite the two to one advantage of the British, it had hardly been a fair fight. Constitution’s heavier guns and heavy timbers were able to both deal out and absorb more punishment than her opponents. Still, it was a fine accomplishment, and both the Navy and the American press were quick to sing the praises of ship and crew. Constitution’s adventures were not over yet, however, so stay tuned!
 Charles Stewart to the Secretary of the Navy, 15 May 1815, Captain’s Letters to the Secretary of the Navy, RG 45, Microfilm 125, Reel 44, NARA.
 Henry B. Joslin, “Naval Asylum Biographies,” Navy Library, Washington, DC.
 USS Constitution Log, 21 Feb. 1815, 24, Microfilm 1030, NARA.
 Joslin, “Naval Asylum.”
 George Douglas to First Secretary of the Admiralty, 22 Feb. 1815, ADM 1/170, National Archives,UK.
 The Letterbook of Pardon Mawney Whipple, 1813-1821, USS Constitution Museum collection.