Mad Jack Oldham Starts the Pequot War

War between the early English colonists of New England and the Native Americans already here was perhaps unavoidable, though it wasn’t the goal of the Pilgrims when they crossed the Atlantic. But then Mad Jack Oldham changed everything.

John Oldham was an early arrival to the new colony in 1623. He, his wife and his sister arrived aboard the Anne, and religious intentions did not drive him to America. Rather, at age 21, it was ambition that fueled him. He had come to make a fortune in the new world.


William Bradford

Men unaffiliated with the Pilgrim religious cause had come to America “on their particular,” Plymouth’s governor William Bradford would write. Without an affiliation with the Pilgrims, Oldham and others like him agreed to abide by the Pilgrims’ laws. They would pay taxes and participate in defending the burgeoning colony. They would also refrain from trading with the American Indians.

In the Pilgrims’ plan, peaceful trade with the Indians would support their economy. It would provide the profit England wanted, and they had to handle it delicately. Men like Jack Oldham and the other ‘particulars’ were to keep to selling and reselling goods to the settlers in Plymouth and along coastal New England.

Jack Oldham, Troublemaker

mad jack oldham

The Mayflower

Oldham and 10 other “particulars” almost immediately started trouble. Oldham refused to stand watch, provoked Miles Standish and raged at him as a ‘beggarly rascal.’ With little in common with the Pilgrims, Oldham’s pugnacious nature came to define him.

Shortly after arriving, Oldham and other malcontents wrote to England of their complaints against the Pilgrims. He criticized the new, godly world they were trying to construct. And he complained of their religious practices, the bad water, thievery in the community and too many mosquitoes.

Bradford intercepted Oldham’s letters. When they were shipped to England a reply to the complaints from Bradford accompanied them. He wrote a point-by-point rebuttal and the sarcastic observation that men like Oldham were “too delicate and unfit to begin new plantations and colonies . . . till at least they be mosquito-proof.”

Jack Oldham was furious when he learned Bradford had intercepted his letters, and his angry and quarrelsome nature sealed his fate.


While the Pilgrims needed manpower and knew there was strength in numbers, they weren’t desperate enough to need a man like Oldham. They banished him from Plymouth in 1624. At first, Oldham flourished under his new freedom. Liberated from the Pilgrims’ taxes and rules, he settled at Nantasket and would go on to be one of the founders of Wethersfield, Conn.

He traded profitably with the Indians, as well as other settlers, and even gained positions in Massachusetts’ early government. But his demeanor got the best of him.  Fellow outcast Thomas Morton described him as “a mad jack in his mood.”

In July 1636, American Indians, probably Narragansetts, waylaid his ship on a trading trip to Block Island. They killed Jack Oldham and several members of his crew. His two nephews returned to land.

The death of Mad Jack Oldham was a flashpoint in the ongoing friction between some of the Indians and the colonists over trade and other matters.


Gov. Endecott invades Block Island

The Narragansetts convinced the colonists that the Pequot tribe harbored the Indians who killed Jack Oldham. Though it was perfectly plausible that Jack Oldham provoked the fight that killed him, ministers throughout Massachusetts spoke out against the murders. Massachusetts Governor John Endecott was ordered to retaliate.

Ninety men invaded Block Island, and killed one Indian there. Thus started the Pequot War, which wouldn’t end until 1638.

This story was updated in 2022.

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