Tisquantum was a native of Patuxet, living at present-day Plymouth; the Patuxet belonged to the Wampanoag confederation. Nothing is really known about Squanto's early life. His history picks up in 1614, when Captain John Smith and some of other ships under his command arrived to map Cape Cod and vicinity. John Smith is perhaps better known for having been rescued by Pocahontas at the Jamestown Colony several years earlier. After Smith completed his exploration and mapping of the harbors, he departed, leaving behind an associate, Thomas Hunt, to trade with the Indians. John Smith had hopes of founding a plantation in New England, and so wanted to engage the Indians in trade.
Thomas Hunt, however, had other plans. Offering to trade beaver, Hunt lured 24 Nauset and Patuxet Indians onboard his ship and took them captive. John Smith would later write that Master Hunt "most dishonestly, and inhumanely, for their kind usage of me and all our men, carried them with him to Malaga, and there for a little private gain sold those silly salvages for rials of eight." Sir Ferdinando Gorges, head of the Council for New England, remembered it similarly: "one Hunt (a worthless fellow of our nation) set out by certain merchants for love of gain; who (not content with the commodity he had by the fish, and peaceable trade he found among the savages) after he had made his dispatch, and was ready to set sail, (more savage-like than they) seized upon the poor innocent creatures, that in confidence of his honesty had put themselves into his hands."
Hunt stored the Indians below the hatches, and sailed them to the Straits of Gibraltar, and on to the city of Malaga, Spain, where he sold as many of them as he could. But when some local Friars in Malaga discovered that they had been brought from America, they took custody of the remaining Indians, and instructed them in the Christian faith. As Sir Ferdinando Gorges states, the Friars "so disappointed this unworthy fellow of the hopes of gain he conceived to make by this new and devilish project."
The Nauset and Patuxet tribes were outraged by the kidnappings, and became extremely hostile. English and French ships visiting Plymouth and Cape Cod were no longer welcomed with profitable beaver trade, as an unwitting French captain and crew would discover in 1617, when their ship was burned and almost everyone killed (a few were enslaved) by the Nauset.
But outrage and vengeance against Europeans would soon become a low priority amongst the Nauset and Patuxet. In 1618 and 1619, a devastating plague, described variously in historical sources as either tuberculosis or smallpox (and perhaps a combination of both), wiped out the entire village at Patuxet, and many surrounding areas were heavily hit.
One Patuxet did survive, however: Tisquantum. He had somehow found himself passage from Malaga, Spain into England, where he began living with John Slaney in Cornhill, London, and began picking up the English language. John Slaney was the treasurer of the Newfoundland Company which had managed to place a colony at Cupper's Cove (Cupids), Newfoundland in 1610; he employed Tisquantum, presumably as an interpreter and as an expert on North American natural resources. He was sent to Newfoundland, and worked there with Captain John Mason, governor of the Newfoundland Colony.
While in Newfoundland, Tisquantum encountered a ship's captain by the name of Thomas Dermer, who had worked with Captain John Smith, perhaps even on the 1614 mapping expedition in which Squanto had been originally taken. Dermer was employed by the New England Company, headed by Sir Ferdinando Gorges; they still had hopes to profit from beaver trade with the Indians of Massachusetts: but this would not be possible as long as hostilities remained. Thomas Dermer recognized that Tisquantum, who had now been living with Englishmen for a number of years, could act as an interpreter and peacemaker between the English and the still-enraged Indians of Patuxet and Nauset. He sent a letter off to Sir Ferdinando Gorges expressing the good use Tisquantum could be put to, and Gorges had them come back to England to discuss their plans.
In 1619, Captain Dermer and Tisquantum set off for New England, to attempt to make peace and re-establish trade with the Indians, and to map out the natural resources that could be exploited by the Company. But upon arriving, they discovered Tisquantum's town, all the Patuxet, were dead from the plague. He did make contact with Massasoit, and his brother Quadequina, the heads of the Wampanoag Confederation, and in the absence of his own people he took up residence with them. Their plan to make peace foiled by the fact that Tisquantum's tribe had been completely wiped out, Dermer continued on to see if he could make peace with the Nauset. He was attacked and taken captive. Tisquantum, hearing about the incident, came to Dermer's rescue and negotiated his release. Dermer would continue on south without Tisquantum, where he was attacked again at Martha's Vineyards. He would die of the wounds after reaching Jamestown, Virginia.
Tisquantum's return home in 1619 was just in time for the Mayflower Pilgrims, who pulled into Provincetown Harbor in November 1620. The Pilgrims sent out their own exploration parties, and during their third expedition they were attacked in camp early one morning by the Nauset. Shots were fired and arrows flew heavily, but in the end nobody was injured and the Nauset fled back into the woods. The Pilgrims continued their expedition around Cape Cod, eventually ending up in the abandoned Patuxet territory, where they decided to settle (the area had been named Plymouth by John Smith on his 1614 mapping expedition).
The Pilgrims lived out of the Mayflower, and ferried back and forth to land to build their storehouses and living houses: they labored all through the winter months of December, January, February, and didn't start moving entirely to shore until March. And during that entire time, they saw almost no signs of any Indians, aside from a few fires burning in the far distance. On March 16, they got a surprise: an Indian named Samoset walked right into the Colony and welcomed them in broken English. Samoset was from an Indian group in Maine, and had picked up a few English words from the fisherman that came into the harbors there. He informed them there was an Indian, Tisquantum, who had been to England and could speak better English than he could. Tisquantum made his first appearance on March 22, at which time he brought Massasoit and Quadequina. The Pilgrims used the opportunity to negotiate a peace treaty and to establish trading relations.
Tisquantum would soon become an integral member of the Plymouth Colony, translating and negotiating between Plymouth's governors (John Carver, and later William Bradford) and tribal leaders including Massasoit. Peace was made with the Nauset, with whom they had their initial conflict on Cape Cod; and peace was negotiated with a number of other Indian leaders within the Wampanoag Confederation. Tisquantum was a guide, taking the Pilgrim ambassadors to various locations, and helping them establish trading relations. He also taught the Pilgrims how to better utilize the natural resources: how to catch eels, and how to plant corn using fish caught from the town brook as fertilizer.
But Squanto's new-found power soon began to corrupt him. He realized that the Indians had a significant fear of the English, especially their guns and technology. He leveraged this fear for his own private benefit, exacting tributes to put in a good word for someone, or by threatening to have the English release the plague against them. Squanto even went so far as trying to trick the Pilgrims into a show of military action, by claiming certain Indian groups were in conspiracy together to fight the English: but he went too far, and his treachery was discovered by both the Pilgrims and the Indians.
When Massasoit learned that Squanto was abusing his power and deceiving for personal gain, he ordered the Pilgrims to turn him over for punishment (death). The Pilgrims were obligated to do so, by the peace treaty they had signed: but at the same time they realized that the survival of their Colony depended on communication with the Indians. But Massasoit had called their hand, and William Bradford was minutes away from turning Squanto over for execution, when a ship came onto the horizon. Not knowing whether it was friend or foe, and even suspecting that perhaps the Indians were in conspiracy with the French, Bradford refused to turn over Squanto until the identity of the ship was discovered. The ship turned out to be the Fortune, and for Squanto it was very good fortune it arrived. The new settlers, the shortage of food, and the oncoming winter distracted from other events. Then as spring came, new settlers showed up to found another colony, at Wessagussett: and they had all kinds of problems with the Indians that required Squanto's interpreting skills. Massasoit, though clearly disappointed and frustrated, did not bother asking for Squanto's life again.
But Squanto's life was not to last long anyway. On one trip to trade for some corn seed for the subsequent growing season, he went with Governor Bradford south on the ocean-side of Cape Cod, and they pulled into Manamoyick Bay because of dangerous weather conditions. There, in November 1622, Squanto's nose began to bleed. He told Governor Bradford it was a sign among the Indians of death. He asked Bradford to pray for him so that he could go to the Englishman's God in Heaven when he died, and asked Bradford to give various things as gifts to his English friends back at Plymouth. Within a few days, he was dead.