He was now no better off than when he first began. David, however, agreed to build a boat for him if he would furnish the material. When the boat was completed Paul, with borrowed money, bought a cargo and started for Nantucket. On the way he was chased by the pirates and compelled to return to Westport to refit his boat which was damaged by striking a rock. He still persevered, reached Nantucket, and sold his cargo. Financially it was not a profitable voyage.

On a second voyage the pirates robbed him of his cargo and inflicted personal injuries, but a third voyage netted good returns. Soon he procured a covered boat and employed a helper. From now on the business adventures of Cuffe brought him large profits. The war was over and the new Constitution was in operation—two reasons why the sea was safer and business more promising. With his new eighteen ton boat he sailed from his rented home on the Westport River for Saint George for a cargo of codfish. The voyage was the foundation for a profitable fishing industry near his home for many years.

At this time Michael Wainer, his brother-in-law, an Indian, entered his service. His brother-in-law was a good seaman and with a new twenty ton vessel, the Sunfish, the men made two trips to the Strait of Belle Isle and Newfoundland. With the profits from the ventures he built in connection with another person, the Mary, a forty-two ton schooner.

In the Mary, accompanied by two small boats, and with a crew of ten, they went on a whaling expedition to the Strait of Belle Isle. On reaching the Strait, Cuffe found four other vessels fully equipped with boats and harpoons. These vessels would not, as was customary, cooperate with Captain Cuffe, so he and his crew went at it alone. Now fearing they might get no whales the strangers fell in with the Mary. Seven whales were captured, six by the crew of the Mary. Two whales were the victims of Cuffe's own hand. Reaching Westport in the autumn of 1793 he proceeded to Philadelphia with his cargo of oil and bone and exchanged it for bolts and iron with which to build a new vessel.[6]

Accordingly the keel for a sixty-nine ton vessel was laid at Westport and in 1795 it was launched. He called it the Ranger. With a cargo valued at $2000, he sailed for Norfolk on the Chesapeake. From here he went to Vienna on Nanticoke River to buy corn. On reaching port it is said the townspeople "were filled with astonishment and alarm. A vessel owned and commanded by a black man, and manned with a crew of the same complexion, was unprecedented and surprising. Suspicions were raised, and several persons associated themselves for the purpose of preventing him from registering his vessel, or remaining among them. On examination, however, his papers proved to be correct and, therefore, the custom house officers could not legally oppose proceeding in a regular course. Paul combined prudence with resolution, and on this occasion conducted himself with candor, modesty, and firmness; his crew also behaved not inoffensively but with conciliating propriety. In a few days the inimical association vanished, and the inhabitants treated him and his crew with respect and even kindness."[7] Another writer affirms "Many of the principal people visited his vessel, and at the instance of one of them, Paul dined with his family in the town."[8] The investment in corn proved so profitable that a second voyage was made to Vienna. On the two trips Captain Cuffe cleared about $2000. The Ranger also made a trip to Passamaquoddy to get a cargo for James Brian of Wilmington.

In 1800 there was launched the Hero, a hundred and sixty-two ton bark, in which Captain Cuffe had one-half interest. This vessel, on one of its trips, rounded the Cape of Good Hope. In 1806 the Alpha was fitted out. This was a ship of two hundred and sixty-eight tons in which the Captain had three-fourths interest. Captain Cuffe with a crew of seven Negroes commanded the Alpha in a voyage from Wilmington to Savannah, thence to Gottenburg, Sweden, and from there to Philadelphia. Cuffe also owned one-half of the one hundred and nine ton brig, the Traveller, built in 1806. Of this ship more will be said elsewhere.

Captain Cuffe was now slightly beyond middle age. Instead of a small open boat, trading with the neighboring townsmen, he had obtained a good sized schooner. "In this vessel," to quote from the funeral oration, "he enlarged the scope of his action, trading to more distant places, and in articles requiring larger capital, and thus, in the process of time, he became owner of one brig, afterwards of two, then he added a ship, and so on until 1806, at which time he was possessed of one ship, two brigs, and several smaller vessels, besides considerable property in houses and lands."[9]

Family Affairs

In the Cuffe manuscripts there is a laconic note chronicling this important event in Paul's life.