“If they catch you at disadvantage, the mines for your life is the word;
and so we fight them with our colours nailed to the mast.”

- Sir Walter Scott: The Pirate, 1821.

For over 4,000 years humanity has used some sort of device to communicate when not within hearing distance like smoke signals, drums, flashing lanterns or lights. Many times they would correspond with vexilloids which were metal or wooden poles with engravings on top. About 2,000 years ago, pieces of colored fabric or material were added to some of these vexilloids as a decoration, so they could be more readily recognized as a symbol, or for sending a signal.

Usually, they were intended as messages from a person or a group of people telling who they are or which group they belonged to. Eventually these flags or ensigns became the banner of a military and the colors representing their standard was in the form of a cloth or piece of silk with figures, colors, or arms upon them which were then attached to a staff, and usually carried by an officer at the head of a company or troop.

These ensigns were vital because they aided the militias in distinguishing friends from foes in battle. In times of yore, knights carried flags into battle because it was difficult to tell who the knights were when they were dressed up and covered in armor ready for battle. These Knight bannerets looked more like the flags we know today.

The first maritime flags were often solitary-colored banners and came into use during the Middle Ages. Today’s international maritime law absolutely necessitates a ship of war to fly its ensign, or flag, before firing on the enemy or at the commencement of any hostile acts.

Striking the ensign, or lowering it from the mast, was and is across the world the standard signal of surrender. Surrender is dated from the time the ensign is struck. Ensigns eventually came to be more commonly called “colors” in battles and as a result many lively idioms arose.

For example to come through with flying colors is an expression dating from the 1600’s meaning “to win or succeed.” Victorious ships at war would sail with their flags high. A century later a similar phrase appeared, "to show one’s true colors" meaning to:

Reveal oneself as one really is, as in We always thought he was completely honest, but he showed his true colors when he tried to use a stolen credit card.

So merchantmen and flotillas used flags to identify other ships and for the most part carried an assortment of ensigns on board. Eventually each nation adopted its own flag for easier identification and solidarity. Pirates were no different, for they considered themselves a nation even though it was one of a criminal nature and the previous turn of phrase harkens back to the late 1600s antonym, false colors, that is, sailing under a flag other than one's own.

Pretense, misrepresentation, or hypocrisy; deceptive statements or actions. For example, She's sailing under false colors - she claims to be a Republican, but endorses Democratic legislation.

Sailing under false colors came from the practice of privateers and pirates, running a specific flag on the masts of their ships purposely to decoy another vessel near enough to be captured and looted. In due course, two flags became theirs and all who saw them in their spyglasses feared the meeting to come.

English privateers flew the red jack by order of the Admiralty in 1694. When the War of Spanish Succession ended in 1714, many privateers turned to piracy and some retained the red flag, for red symbolized blood. No matter how much seamen dreaded the black pirate standard all prayed they never encountered the jolie rouge. This red flag boldly declared the pirates’ intentions. No life would be spared. No quarter given.

Various forms of the jolie rouge appeared at sea and eventually pirates adopted another flag as their emblem, the familiar skull and crossbones on a field of black instead of red, those who saw these Jolly Rogers recognized the implied warning. To further coerce their victims, pirates used other symbols. Thomas Tew and Calico Jack Rackham used swords on the flags to stand for power over life. By adding an hourglass with wings Christopher Moody made it clear that time was running out. Dancing skeletons indicated that the pirates cared little for their fate and they toasted their victims’ deaths with a raised glass.

Pirates preferred to wage psychological warfare and woe to any merchantman that dared to defy the warning. These buccaneers earned their living by capturing cargos and ransoming captives, but there was the problem with pirating. To engage in combat against their opponent imperiled the anticipated cargo and ship they meant to seize. A fight could also mean their own deaths. Hence the need for two flags: the red jack and the Jolly Roger. Rather than resort to physical violence some pirates gave quarter. When pirates overtook his ship in 1724 Captain Richard Hawkins noted… they all came on deck and hoisted Jolly Roger... When they fight under Jolly Roger, they give quarter, which they do not when they fight under the red or bloody flag.

The previous examples show the vast importance given to the ensign during naval engagements and that striking the colors was collectively understood as an indication of the laying down of arms. It was and is still a crime to continue to fight after striking one's colors, and a crime to persist in firing on an adversary after he has struck his colors, unless he designates with some other action, such as continuing to fire or seeking to escape as proof that he has not truly surrendered.

    Oh, better that her shattered bulk
    Should sink beneath the wave;
    Her thunders shook the mighty deep,
    And there should be her grave;
    Nail to the mast her holy flag.

    -Oliver Wendell Holmes, Old Ironsides

Across the ages there have been many battles at sea where the captain has decided for one reason or another to resolve or declare an act of volition by nailing his colors to the mast.

To fight or hold out until the bitter end; to refuse to compromise, concede, or surrender; to persist or remain steadfast, especially in the face of seemingly overwhelming opposition.
By nailing their colors to the mast meant that there would be no surrender and the Captain was displaying his intention to hold out until the bitter end. This became a term for no surrender and when it's used in modern day parlance it describes taking an action that is irreversible.

Of all the naval duels in history it is John Paul Jones, who stands alone when it comes to leaving an enduring and prominent name in history for the struggle for independence during the American Revolution. Probably the most famous story about nailing one’s colors to the mast occurred on September 23, 1779.

Before going into battle against the Continental Navy ship Bonhomme Richard, Captain Richard Pearson, of the Royal Navy and commander of HMS Serapis, with his own hands nailed the British ensign to the ensign staff.

With a squadron of three ships led by the Bonhomme Richard, Captain John Paul Jones met Captain Pearson with the Serapis and one other ship who were, “convoying a fleet of merchant vessels off the coast of Flamborough Head, Scotland, and at once the two flagships engaged in a desperate conflict.”

The battle continued through the long hours of that September night in 1779. Cannons boomed across the waters and in the middle of the clash Jones ran his vessel into the Serapis. There was a pause in the fire. During the intense fighting between the Bonhomme Richard and the Serapis, Bonhomme Richard‘s ensign had been shot away and Captain Pearson called out, "Have you struck your colors?"

The infamous reply by John Paul Jones was "I have not yet begun to fight!"

The commanding officer of the Richard lashed the two ships together and a bloody battle ensued until the decks of both were littered with dead and dying. Around ten o’clock p.m. a hand grenade from the Richard was lobbed into the hatchway of the Serapsis and row of cartridges burst into flames leading to an appalling explosion where twenty men were blown to pieces.

Still both commanders tenaciously raged on in vicious battle until both ships were on fire, and half their crews were dead or wounded. At last the Serapis surrendered and both vessels were in ruins.

Captain Richard Pearson had to tear down the ensign he had nailed to the mast of the Serapis when surrendering and the Bonhomme Richard sank the next morning.


Cliches origins:

Nautical terms and Phrases:

Naval operations of the Revolutionary War:

The Phrase Finder:

Pirates & Privateers: the History of Maritime Piracy :

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