Bellamy after leaving the Cape, sailed south and at Newport met Paulsgrave Williams who came from a successful family. Williams joined Bellamy on his adventure for gold. They had no luck diving for treasure off the coast of Florida. Not wanting to go back to New England with no treasure, they resorted to going after moving, visible boats on the surface of the water. The two men joined Captain Benjaman Hornigold's pirate crew; Hornigold was the captain whose ship Blackbeard first joined upon coming to the Caribbean.
In June 1716 the pirates of Hornigold's ship voted to attack ships of all nations in opposition to their captain who would only attack French and Spanish ships. The crew elected Bellamy as captain. With Bellamy as Captain and Williams as quartermaster and second in command, they went on an "orgy of plundering" in the Caribbean for the next several months. In February 1717 Bellamy and Williams each in command of their own ships and working together, went after the ship the Whidah Galley headed for Jamaica from London. The pirates chased the Whidah Galley for three days before finally capturing it. They gave the captain and crew of the Whidah Bellamy's old ship the Sultana and kept the Whidah or Whydah with all its gold, silver and ivory for themselves.
By sometime in March 1717 Bellamy and Williams headed their ships toward New England. There was a brief stop in the Chesapeke where Bellamy was afraid of encountering a war ship. On their way north again, they captured and plundered another ship with a Captain Beer. Bellamy's crew wanted to sink Beer's ship, Beer refused to join the pirates, and Bellamy known for his speeches to prisoners told Beer:
"Damned my Blessed, I am sorry they won't let you have your sloop again, for I scorn to do any one a Mischief, when it is not for my Advantage. Damn the sloop, we must sink her, and she might be of Use of you. Tho' damn ye, you are a sneaking Puppy, and so are all those who will submit to be governed by Laws which rich men have made for their own security....."
Almost within reach of Maria Hallet on April 26, 1717, Bellamy was sailing along the outer shore of Cape Cod at night when a strong storm sunk the Whydah. The ship went down with all aboard except for eight pirate crew members who managed to get to shore and were captured. Six were hanged, the other two pleading that Bellamy had held them against their will.
