Disaster ~ Captain John “Mad Jack” Oldham ~ 52 Ancestors #9

Plimoth_Plantation.I believe that one of the best parts of Genealogy is finding the stories of our Ancestors that show them in a “not so good light”. It shows us that they were just like us, doing the good things, the bad things, and even a few ugly things. This prompt helped me to find this story about my 10x Great Uncle, Captain John “Mad Jack” Oldham. I was surprised and excited to see so many twists and turns that guided his life. Bonus points, he did the good, the bad and the ugly!

The Anne

John was born on April 9, 1592, in Derbyshire, England. He was the son of William and Philippa (Sowter), Oldham. The Oldham’s were a well to do family in the area. In the Spring of 1623, 3 years after the Mayflower arrived at Plymouth, John boarded the ship, The Anne, along with his sister Lucretia, his brother Thomas, and his brothers’ wife Elizabeth Rhoades who was pregnant. They landed there in the Summer of 1623.

It was soon made obvious that John did not fit in with the Puritans, They had come for religious reasons and he had come for monetary ones. He was determined to become wealthy in this new land. He had purchased 10 acres of land in Plymouth before leaving England which meant he owned more land there than anyone else. This included Edward Winslow who was the Governor of the area. William Bradford said of John “He is a rough and ready man, a man of considerable practical ability, but heady, self-willed, and of an ungovernable temper.”  John became dissatisfied with the way things were run and by the Pilgrims Holier-than-thou attitudes. When Reverend John Lyford arrived in 1624 the two men developed a close bond. Bradford also said about the two’s friendship “They were plotting against them and disturbing their peace, both in respects of their civil and church-state.”

Wethersfield John Oldham PlaqueJohn began to write letters of complaint against Winslow, Bradford, and Brewster. They were to be sent by ship back to England, but Bradford opened them and read them before the ship left. Upon finding out what happened to the letters, John became “A Mad Jack in a mood” and he lashed out. Miles Standish was head of the Military and he tried to stop John who pulled a knife and yelled at Miles “You are a Rascal! A Beggarly Rascal”. These were harsh words for that time. He was brought up before the court and as a result, he and Lyford were banished from Plymouth, an extreme punishment in this wild frontier. 

John Oldham path rock marker

He, Lyford and 10 other men left Plymouth and were the first to set out along the old Connecticut Path to establishing Wethersfield Ct, the first English settlement on the Connecticut River. John Oldham was considered the first Englishman to conduct explorations there. After his trip north, there was a severe outbreak of smallpox. Many natives, including the Pequot, held him responsible for the death of thousands from Maine to New York. John became a successful sea captain, merchant, and Indian trader. He grew rich in coastal trade and trading with the Indians. He was made the overseer of shot and powder for Massachusetts Bay Colony.,

oldham mad jack marker block island

John made several trips to England and back and on one trip he brought his 2 nephews to live with him. In July 1636 he was on a voyage to trade with the Indians on Block Island. On July 20 his boat was boarded by a band of 14 angry Indians, presumed to be from Pequot tribes. The attack was due to a disagreement over a previous trade. He and five of his crew were brutally murdered, his ship was seized by the Indians and his two nephews were captured by the Indians, but they were later rescued. The ship’s cargo was looted. The Bay Colony was outraged at this latest incident and sent John Endicott with a force to retaliate. This is thought of as the incident that caused the Pequot War and brought about the extinction of that tribe by the following year.

John Oldham definitely experienced a lot of disasters in his 44 years of life. Not only in his personal life but to all those around him. There is so much written about him I could probably write 8 more blogs and not repeat myself. Who knows, I might just do that in the future.



I am a professional genealogist, writer, photographer, wife, mother, and grandma. I have two books available on Amazon.com: Your Family History: Doing It Right the First Time and Planning Your Genealogy Research Trip. You can also connect with me via Facebook or Twitter.