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Mad Jack Oldham and the Start of 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 he was not driven to America by religious intentions. Rather, at age 21, it was ambition that fueled him. He had come to make a fortune in the new world.

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 that they would abide by the Pilgrims' laws, pay taxes and participate in defending the burgeoning colony and refrain from trading with the American Indians.

In the Pilgrims' plan, peaceful trade with the Indians was to be the basis of their economy. It would provide the profit England wanted, and it had to be handled delicately. Men like Oldham and the other ‘particulars’ were to keep to selling and reselling goods to the settlers in Plymouth and up and down the New England coast.

mad jack oldhamOldham 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 was his defining characteristic.

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

Bradford intercepted Oldham’s letters, and 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.”

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, Connecticut.

He traded profitably with the Indians, as well as other settlers, and even gained positions in Massachusetts’ early government. But his demeanor – ‘a mad jack in his mood,’ fellow outcast Thomas Morton would write of him – got the best of him.

In July 1636, his ship was waylaid by American Indians, probably Narragansetts, on a trading trip to Block Island. He and several members of his crew were killed. His two nephews were returned to land. His death was a flashpoint in the ongoing friction between some of the Indians and the colonists over trade and other matters.

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

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


  1. Grant Menzies

    Brother of my ancestor Lucretia, wife of Jonathan Brewster.

  2. Bill Carlson

    Without Myles Standish the war might have been lost. His actions were the first acts of genocide in the New World.

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