Thomas (1621 - July 6, 1710), known as “The Trooper,” is the earliest individual named Prentice to whom our ancestry has definitely been traced so far. According to the Essex Record Office in Essex County, England (not too far from London), he married Grace Bull at a village called Earls Colne in 1647. With their young daughter Grace, they emigrated from England to Cambridge, Mass. in 1648 or 1649, roughly twenty-nine years after the Mayflower’s voyage. They had seven other children in the New World.
     Thomas and Grace were probably born and raised in Earls Colne. The will of Francis Nicholson of Ipswich, County of Suffolk, England, found in English Origins of New England Families, gives us a clue that they were probably landowners before they left England. In it Mr. Nicholson makes mention of the lands he had bought of William and Thomas Prentice in Gaines Colne and White Colne, County of Essex. His will was probated in 1656, about seven years after Thomas emigrated. Thus, it seems likely that Thomas had lived in Essex County, then sold his share of the land in anticipation of his departure. As to why he left, it may have been because of a desire for religious freedom, or because of the political turmoil caused by two civil wars raging in England throughout the 1640’s. These culminated in the defeat and execution of King Charles I at the hands of Oliver Cromwell. Many battles were fought in Essex County, probably making it a less than ideal place to raise a family. (The uncertainty about Thomas and Grace's ancestry is due to the fact that many records of genealogical importance were destroyed during the wars.)
     Many left England to get away from the tyranny of the Church of England, but found that the government in the Colonies was controlled almost as tightly by the Puritan churches there. Before one could vote in civil elections, he had to become a “freeman,” a member in full communion with the local church congregation. (In many places, too, only landowners could vote.) Sometimes it took many years to become a freeman. Thomas must have fit in well, because he and his family joined the First Church of Cambridge, a Puritan church, in 1652. He was made a freeman that same year, only three or four years after he arrived in Massachusetts.

     Some other notable events in his life:

Thomas enlisted in the cavalry while Cromwell was still ruling England. He was promoted to Lieutenant of the Troop of Horse in 1656 and Captain in 1662. He met with great success in the Indian wars of the late 1600’s (including King Philip’s War in 1675-6 immortalized in The Last of the Mohicans) and received several sizable land grants as a result. He distributed these to his descendants during his lifetime.

In 1667 he was sent to lay out and settle Quinsagamond (later Worcester, Mass.) and had one of the first houses there.

He was a representative to the Mass. General Court from 1672-1674.

In 1675 Capt. Prentice was commissioned to rebuild Lancaster, Mass., which had been destroyed by hostile Indians in Philip’s War..

Also in 1675 he and his troop are mentioned nineteen times in the books of the treasurer of the Massachusetts colony.

After the “Glorious Revolution” drove King James II from the British throne in 1688, Captain Prentice was sent to Rhode Island to arrest the king’s envoy to the Colonies, Sir Edmund Andros, and bring him to the ship to be taken to England for trial. (See Capt. Prentice’s letter below.)
    Andros was notorious for trying to confiscate the charters of the colonies. When he demanded Connecticut’s charter, someone extinguished the lamp in the meeting hall and hid the charter in a hollow oak - the “Charter Oak” - which became a famous landmark until it was cut down in 1856. This tree is memorialized on the back of the Connecticut quarter, minted in 1999.

In 1691, at the request of the Indian Christians, Thomas was appointed their overseer and magistrate. Apparently, he was one of the “good guys” who followed the Apostle Eliot's lead.

In 1692 his wife Grace died.

Aug. 8, 1689
To the Hon^ed Governor and Counsill:
      And please your Honors, having received orders from you with my Troop to Bristoll to move, in order to receive Sir Edmond Andros from the Gentlemen at Rhod. Island, from Roxbury, about 3 of the clock, we moved away to Mr. Woodcock’s, on Wednesday, to Bristoll, just after noon; coming to Rhod. Island same day; the counsill being discoursed with much civilitie, they delivered Sir Edmond, and with a passag boate, sent us to Bristoll. And Sir Edmond complaining of indisposition of body to ride, either swift or far together, our return will not be as your Honors may expect. The Gentlemen of Bristoll favored us with their advise and company to Rhoad Island. Please your Honors, it is requested by Sir Edmond, and requested by the forenamed Gentlemen, that Sir Edmond may be conveyed by Dorchester to the Castle, if your Honors please there to secure him, and upon our approach towards Boston we will give you an account thereof for suitable opportunitie for our guarding him to foresaid place. This being in hast. for opportunitie of sending.

I subscribe, Your Honors, humble servant,
     THOMAS PRENTICE, Capt.