During the early 1670s, de Graaf either escaped the plantation or was freed, and it was recorded that he married his first wife in 1674 in the Canary Islands before moving on to the Caribbean. Not long after his marriage, de Graaf took to the sea, and was reportedly captaining a French privateer vessel by 1675. By the late 1670s, de Graaf had turned to full blown piracy and captured a series of increasingly large vessels, trading up several times before finally in 1679, he captured a 28 gun frigate belonging to the Spanish Armada De Barlovento, which he renamed the Tigre (Tiger).
By 1682, de Graaf was so notorious that Henry Morgan, governor of Jamaica, himself a former pirate, sent a frigate named Norwich to hunt him down. It is not reported if they ever met. Meanwhile, the Spanish sought revenge for the theft of their frigate, and the Armada de Barlovento was also sent to hunt de Graaf down. While in Cuba, de Graaf became aware of the plan to seek him out. Rather than waiting for the Armada, de Graaf sailed immediately in search of it, and soon met with another Spanish vessel named the Princesa. A prolonged gun battle ensued, and the Spanish took heavy casualties. More than fifty crewmen of the Princesa were killed, but de Graaf lost no more than nine. The Spanish surrendered, and de Graaf gallantly put the seriously wounded captain ashore with his own surgeon and a servant. The Princesa was a huge prize, carrying the payroll for all the troops in Puerto Rico and Santo Domingo, about 120,000 pesos in silver. De Graaf traded up again, renamed the ship the Francesca and made her his new flagship, and retired to Haiti.
His next adventure was to go roving with privateer Michiel Andrieszoon in the gulf of Honduras. They sighted two empty Spanish galleons, and so waited in hiding for them to be filled. However, the plan was foiled when fellow pirate Nicholas van Hoorn attacked and captured the empty ships. Van Hoorn proposed to join forces with de Graaf to attack the nearby city of Veracruz, and he eventually agreed. They also joined up with French pirate Michel de Grammont, bringing their combined strength to 5 large ships, 8 smaller vessels and 1300 pirates. On the 17th of May 1683, the pirates attacked. Using the captured galleons as a distraction, de Graaf along with Yankey Willems and a small detachment of men slipped ashore in the early morning to sabotage the fortifications and incapacitate the militia. Van Hoorn marched his men overland to join the attack.
On the second day of plundering, the Spanish plate fleet, composed of numerous warships, appeared on the horizon.The pirates retreated with hostages to the nearby Isla de Sacrificios and waited for ransoms. Impatient that payments did not arrive immediately, Van Hoorn ordered the execution of a dozen prisoners and had their heads sent to Veracruz as a warning. De Graaf was furious; the two argued and then fought a duel. Van Hoorn received a minor slash across the wrist and was returned to his ship in shackles. The wound later became gangrenous and van Hoorn died as a result of the infection a fortnight later.
De Graaf eventually gave up on the ransoms, and the pirates slipped away without engaging the Spanish fleet.
In late November 1683, de Graaf, his compatriots and their fleet of seven ships landed off Cartagena and where they stayed for almost a month waiting to strike at the city. The local governor, Juan de Pando Estrada, commandeered three private slave trading vessels - the 40-gun San Francisco, the 34-gun Paz and a smaller 28-gun galliot. The Spanish had 800 men, but their commander was young and inexperienced. The Spanish launched a pre-emptive strike on Christmas Eve but quickly found De Graaf's more experienced pirates a mighty foe. 90 Spaniards were killed versus only 20 pirates. The San Francisco was grounded and the two other ships were captured. De Graaf re-floated the San Francisco as his new flagship and renamed it the Fortune, later the Neptune. Andrieszoon took the Paz and renamed it the Mutine ("Rascal") and Willems was given command of the Francesca. The group released a large number of Spanish prisoners on Christmas Day and sent them ashore with a note for Governor Estrada thanking him for the Christmas presents. De Graaf and his bolstered fleet then laid siege to the town by blockading the harbour.
The following January, an English convoy, led by the 48-gun HMS Ruby, arrived carrying a note for de Graaf from his wife offering a Spanish pardon and commission. De Graaf did not trust the Spanish to keep their word, and ignored the note, but invited English officers to board his vessels and trade with his men. The English passed through without incident, and soon after de Graaf and his compatriots left for Haiti.
On the 6th of July 1685, de Graaf attacked another town, Campeche. A protracted battle ensued, allowing the Spanish time to flee with all goods and valuables, surrendering the town but giving the pirates no plunder. The pirates settled in to the town, and after two months in the town the pirates, failing to secure a ransom, began to burn the town and execute prisoners and once again, de Graaf stepped in to stop the violence against the hostages. The pirates departed Campeche in September 1685, carrying away many prisoners for ransom.The pirates split up and de Graaf fled from a superior fleet off the Yucatán. After a day-long battle with two larger Spanish ships, de Graaf was able to escape by dumping all his cargo and cannons overboard to lighten the ship. The following February the Spanish staged a raid on de Graaf's plantation on Saint Dominque. In retaliation, de Graaf raided Tihosuco, looting and burning buildings. Returning to Haiti, de Graaf accidentally wrecked his ship while pursuing a Spanish barque, however he managed to take the Spanish vessel with only his ship's long boat.
De Graaf then continued to rove the Caribbean waters, battling with the Cuban coastguard and defending Haiti from invasions. He blockaded the Jamaican coast for six months before departing for the Cayman Islands, and captured a small English sloop en route.In March 1693, de Graaf met and married his second wife, Anne Dieu-le-Veut. He agreed to marry her after she threatened to shoot him for insulting her. De Graaf spent the summer of 1693 making several raids on Jamaica, the English retaliated in May 1695 with an attack on Port-de-Paix at Saint Domingue, where they sacked the town and captured de Graaf's family. De Graaf himself fled to Louisiana, where he died on the 24th of May 1704.
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