His was a short career but in the area of pirate flags his may have been important. He started his short lived adventure in September 1718 and it ended in February 1719. Some sources claim that his crudely drawn skull superimposed over cross bones was the first true jolly roger of its kind.
Richard Worley set out from New
York with eight others in a small open boat; they
were ill equipped and carried few supplies. The crew
set out in late September 1718. Their ship was hardly
seaworthy so they set out down the coast and up the
Delaware River where they captured a boat laden with
household goods (this was not constituted as piracy,
but rather burglary since it did not take place upon
the sea). The next prize taken by these men was more
in keeping with their needs, a sloop out of
Philadelphia. They took the sloop and increased the
size of their band to 12. Within a couple more days
they had taken another sloop that they felt more well
kept than the prior ship and transferred to it.
At this time the governor issued a proclamation for the apprehension of all pirates who had not availed themselves of the King's pardon, and ordered out the Phoenix, a ship of 20 guns, to enforce this proclamation. However, Worley and his band set out to sea and missed the Phoenix which was searching for them in the coastal waters. Six weeks later the pirates returned, having taken another sloop and a brigantine among the Bahama Islands. The company had increased to 25 during this trip and their sloop now mounted 6 guns. Captain Worley and his crew had also adopted the skull and crossbones in their ensign (flag). Articles were signed and the crew were officially 'on account' that they would fight to the end, no quarter asked or given.
They were next sighted off North Carolina where they paused to clean and refit their ship. The governor received this information and outfitted two ships of 8 and 6 guns to trap the pirates, but to no avail as they were gone by the time the ships arrived. Unfortunately, Worley came in sight of the ships and mistaking them for merchants moved to prevent them from entering the Jamestown harbor. Instead of preventing their entry, he ended up trapping himself in the harbor with two ships blocking his escape. True to their articles the pirates fought to the end, taking a broadside from one of the Carolina ships before being boarded. All of the pirates died on board, except for the captain and one other, who were very seriously wounded. Both captured pirates were hanged the next day, February 17th 1719, for fear that their wounds might prevent them from receiving the punishment that was felt due.