John "Mad Jack" Oldham was born circa 1592 in All Saints Parish, Derby, Derbyshire, England, United Kingdom to William Oldham (1568-1636) and Phillippa Sowter (c1568-) and died 20 July 1636 Block Island, Washington County, Rhode Island, United States of unspecified causes. He married Jane Bissell (1598-1663) 1619 in England, United Kingdom.


John Oldham was an early Puritan settler in Massachusetts. He was a captain, merchant, and Indian trader. His death at the hands of the Indians was one of the causes of the Pequot War of 1636-37.

Early life

Oldham was born in Derbyshire, England in 1592, and was baptized at the Church of All Saints (now Derby Cathedral) in Derby on July 15, 1592. A follower of the Puritans from an early age, he emigrated to Plymouth Colony with his sister in July 1623 aboard the Anne. His sister, Lucretia Oldham Brewster, was married to Jonathan Brewster (1593-1659), son of William Brewster (1567-1644), one of the signers of the Mayflower Compact.

Bannishment from Plymouth Plantation

Oldham is proof that relations among the Pilgrims were not always harmonious. Over half of those who sailed on the Mayflower had come for economic opportunity, rather than religious motivations. In 1624, Rev. John Lyford came over to America, and was welcomed at first, but soon disgruntled members of the group who wanted to worship as they had in England, gravitated to him. Lyford gave them encouragement and met with them in secret. Oldham was a supporter of Lyford, and the two of them were looked upon by Pilgrim leader William Bradford as trying to destroy the colony.[5]

Oldham and Lyford wrote letters back to England, disparaging the Pilgrim authorities. Bradford intercepted some of these letters and read them, which greatly angered Oldham. Oldham then refused to stand guard, and argued with the Pilgrims' military advisor, Miles Standish. As a result, they were banished from Plymouth - an extreme punishment in this wild frontier.

Watertown Founders Monument

Watertown Founders Monument

He is listed on Watertown Founders Monument, commemorating the first settlers of Watertown, Massachusetts. The town was first known as Saltonstall Plantation, one of the earliest of the Massachusetts Bay Colony settlements. Founded in early 1630 by a group of settlers led by Richard Saltonstall and George Phillips, it was officially incorporated that same year. The alternate spelling "Waterton" is seen in some early documents.

Move to Nantasket

Oldham recovered nicely though. He grew rich in coastal trade and trading with the Indians. He became a representative to the General Court of Massachusetts from 1632 to 1634. He was the overseer of shot and powder for Massachusetts Bay Colony. Oldham's company granted ten acres in assignment of lands in 1623 presumably for each person in Oldham's family and for the following: Conant, Roger, Penn, and Christian.[10]

In the aftermath of the expulsion of Lyford and Oldham, others who were disaffected left as well. The colony lost about a quarter of its residents, with some going to live at Oldham's settlement at Nantasket, Massachusetts, and some going to Virginia or back to England.

As a trader, Captain Oldham sailed to Virginia and England, but by 1630 he was back in the Massachusetts Bay Colony.

He took up residence on an island in the Charles River and was a member of the church at Watertown. Oldham represented Watertown in the colony's first General Court or assembly in 1634. He continued in the Indian trade, sailing the coast from Maine to New Amsterdam.

In 1633 or 1634, Oldham led a group of ten men (which included Captain Robert Seeley), along the Old Connecticut Path to establish Wethersfield, Connecticut, the first English settlement on the Connecticut River.

Death at Block Island

In July 1636 he was on a voyage to trade with Indians on Block Island. On July 20 he was boarded by hostile Indians, presumed to be Pequots. He and five of his crew were killed, and his two boys with him were captured. The ship's cargo was looted. A fishing vessel rescued the boys and tried to tow his sloop to port. When adverse winds affected them, they scuttled the ship but brought the two boys home.

The Bay Colony was outraged at this latest incident, and sent John Endicott to Block Island with a force to retaliate. His death at the hands of the Indians was one of the causes of the Pequot War of 1636-37.

Family & Marriage

  1. Richard Oldham (1614-1655) - with Father at Block Island attack?
  2. Joseph Oldham (1621-)- with Father at Block Island attack?
  3. Mary Oldham (1621-1646)
  4. John Oldham (1622-1708)
  5. Christine Oldham (1623-)
  6. Christian Oldham (1624-)
  7. Thomas Oldham (1625-1711)
  8. Margaret Oldham (1631-)


Offspring of John "Mad Jack" Oldham and Jane Bissell (1598-1663)
Name Birth Death Joined with
Richard Oldham (1614-1655)
Joseph Oldham (1621-)
Mary Oldham (1621-1646) 1621 England 9999 Massachusetts William Bridges (c1610-)
John Oldham (1622-1708)
Christine Oldham (1623-)
Christian Oldham (1624-)
Thomas Oldham (1625-1711)
Margaret Oldham (1631-)


Offspring of William Oldham (1568-1636) and Phillippa Sowter (c1568-)
Name Birth Death Joined with
Martha Oldham (1593-)
Thomas Oldham (c1594-)
John Oldham (1592-1636) 1592 All Saints Parish, Derby, Derbyshire, England, United Kingdom 20 July 1636 Block Island, Washington County, Rhode Island, United States Jane Bissell (1598-1663)
Lucretia Oldham (1600-1679) 14 January 1600 Derby, Derbyshire, England 4 May 1678 Preston, New London County, Connecticut Jonathan Brewster (1593-1659)



Footnotes (including sources)

‡ General