The Adventure Galley, the ship selected for the cruise, was of 287 tons and thirty-four guns, a powerful privateer for her day, which Kidd fitted out at Plymouth, England. Finding difficulty in recruiting a full crew of mettlesome lads, he sailed from that port for New York in April of 1696, with only seventy hands. While anchored in the Hudson, he increased his company to 155 men, many of them the riff-raff of the water-front, deserters, wastrels, brawlers, and broken seamen who may have sailed under the black flag aforetime. It was a desperate venture, the pay was to be in shares of the booty taken, "no prizes, no money," and sober, respectable sailors looked askance at it. Kidd was impatient to make an offing. Livingston and Bellomont were chafing at the delay, and he had to ship what men he could find at short notice.

The Adventure Galley cruised first among the West Indies, honestly in quest of "pirates, freebooters and sea rovers," and not falling in with any of these gentry, Kidd took his departure for the Cape of Good Hope and the Indian Ocean. This was in accordance with his instructions, for in the preamble of the articles of agreement it was stated that "certain persons did some time since depart from New England, Rhode Island, New York, and other parts in America and elsewhere with an intention to pyrate and to commit spoyles and depredations in the Red Sea and elsewhere, and to return with such riches and goods as they should get to certain places by them agreed upon, of which said persons and places the said Captain Kidd hath notice."

This long voyage was soundly planned. Madagascar was the most notorious haunt of pirates in the world. Their palm-thatched villages fringed its beaches and the blue harbors sheltered many sail which sallied forth to play havoc with the precious argosies of the English, French, and Dutch East India Companies. Kidd hoped to win both favor and fortune by ridding these populous trade routes of the perils that menaced every honest skipper.

When, at length, Madagascar was sighted, the Adventure Galley was nine months from home, and not a prize had been taken. Kidd was short of provisions and of money with which to purchase supplies. His crew was in a grumbling, mutinous temper, as they rammed their tarry fists into their empty pockets and stared into the empty hold. The captain quieted them with promises of dazzling spoil, and the Adventure Galley vainly skirted the coast, only to find that some of the pirates had got wind of her coming while others were gone a-cruising. From the crew of a wrecked French ship, Kidd took enough gold to buy provisions in a Malabar port. This deed was hardly generous, but by virtue of his letters of marque Kidd was authorized to despoil a Frenchman wherever he caught him.

After more futile cruising to and fro, Kidd fell from grace and crossed the very tenuous line that divided privateering from piracy in his century. His first unlawful capture was a small native vessel owned by Aden merchants and commanded by one Parker, an Englishman, the mate being a Portuguese. The plunder was no more than a bale or two of pepper and coffee, and a few gold pieces. It was petty larceny committed to quiet a turbulent crew and to pay operating expenses. Parker made loud outcry ashore and a little later Kidd was overtaken by a vengeful Portuguese man-of-war off the port of Carawar. The two ships hammered each other with broad-sides and bow-chasers six hours on end, when Kidd went his way with several men wounded.

Sundry other small craft were made to stand and deliver after this without harm to their crews, but no treasure was lifted until Kidd ventured to molest the shipping of the Great Mogul. That fabled potentate of Asia whose empire had been found by Genghis Khan and extended by Tamerlane, and whose gorgeous palaces were at Samarcand, had a mighty commerce between the Red Sea and China, and his rich freights also swelled the business of the English East India Company. His ships were often convoyed by the English and the Dutch. It was from two of these vessels that Kidd took his treasure and thus achieved the brief career which rove the halter around his neck.

The first of these ships of the Great Mogul he looted and burned, and to the second, the Quedah Merchant, he transferred his flag after forsaking the leaky, unseaworthy Adventure Galley on the Madagascar coast. Out of this capture he took almost a half million dollars' worth of gold, jewels, plate, silks, and other precious merchandise of which his crew ran away with by far the greater share, leaving Kidd with about one hundred thousand dollars in booty.

It was charged that while on this coast Kidd amicably consorted with a very notorious pirate named Culliford, instead of blowing him out of the water as he properly deserved. This was the most damning feature of his indictment, and there is no doubt that he sold Culliford cannon and munitions and received him in his cabin. On the other hand, Kidd declared that he would have attacked the pirate but he was overpowered by his mutinous crew who caroused with Culliford's rogues and were wholly out of hand. And Kidd's story is lent the color of truth by the fact that ninety-five of his men deserted to join the Mocha Frigate of Culliford and sail with him under the Jolly Roger. It is fair to assume that if William Kidd had been the successful pirate he is portrayed, his own rascals would have stayed with him in the Quedah Merchant which was a large and splendidly armed and equipped ship of between four and five hundred tons.

Abandoned by two-thirds of his crew, and unable to find trustworthy men to fill their places, Kidd was in sore straits and decided to sail for home and square accounts with Bellomont, trusting to his powerful friends to keep him out of trouble. In the meantime, the Great Mogul and the English East India Company had made vigorous complaint and Kidd was proclaimed a pirate. The royal pardon was offered all pirates that should repent of their sins, barring Kidd who was particularly excepted by name. Many a villain whose hands were red with the slaughter of ships' crews was thus officially forgiven, while Kidd who had killed no man barring that mutineer, the gunner, William Moore, was hunted in every sea, with a price on his head.

On April 1, 1699, after an absence of almost two years, Kidd arrived at Anguilla,[[4]] his first port of call in the West Indies, and went ashore to buy provisions. There he learned, to his consternation, that he had been officially declared a pirate and stood in peril of his life. The people refused to have any dealings with him, and he sailed to St. Thomas, and thence to Curacoa where he was able to get supplies through the friendship of an English merchant of Antigua, Henry Bolton by name, who was not hampered by scruples or fear of the authorities. Under date of February 3, the Governor of Barbadoes had written to Mr. Vernon, Secretary of the Lords of the Council of Trade and Plantations in London: