Samuel Bellamy is believed to have been born to Stephen and Elizabeth (Pain) Bellamy (married May 31, 1672) at Hittisleigh near Plymouth in Devonshire in February 1689. Baptized on March 18, 1689. His mother dying shortly after his birth (buried February 28, 1689), Bellamy probably grew up with his two brothers and three sisters on the streets of Plymouth. He may have gone to sea at an early age. His later displays of unusual leadership and daring as a pirate captain indicate that he probably had military experience—either in the Royal Navy, or as a privateer—during the War of Spanish Succession (1702-1713).

Centuries-old Cape Cod tradition has it that Sam came to Cape Cod after the war where he met and fell in love with Maria Hallett. Her parents wanted something better for her than a footless sea-faring man, however, and forbade the two to wed. Bellamy accordingly took a crew to the West Indies to search for a sunken treasure ship—and a fortune with which to marry Maria. Treasure-hunting is, however, easier said than done. Legend has it that Bellamy turned pirate after the expedition failed, rather than return to her with empty hands.

Bellamy turned pirate as early as the fall of 1715, but no later than January 1716. Worked briefly with Henry Jennings, and then joined the pirate flotilla led by Ben Hornigold (aka “Horn o’gold”). Hornigold was ousted as commander of that flotilla in the summer of 1716, and Bellamy was elected in his place. Like many pirates of the early 18th-century, he was motivated by a spirit of revolt against political, social, and economic oppression. He and his crew considered themselves rebels rather than robbers, and called themselves "Robin Hood’s Men"--after the famous English outlaw of the Middle Ages. This is reflected by the pirates' "constitution"--known as "The Articles". These democratic rules included surprisingly modern elements of "Liberty, Equality and Fraternity".

The capture of The Whydah Galley, a homeward-bound English slaver, was the pinnacle of Bellamy's career. According to court testimony, this vessel had 20-30,000 pounds sterling in silver and gold aboard at the time of her capture. Given that an honest sailor's pay for a month was perhaps two pounds sterling, this was an immense fortune for the men in Bellamy's pirate fleet. He transferred his command to the Whydah, and, after a few more robberies, turned the bow of his new flagship northward. Was he returning for Maria? We may never know. But what is known is that his "floating commonwealth" came to grief in a nor'easter on a Cape Cod sand bar.

He was 29 years old and he and his men had taken over fifty ships in the span of a little more than a year