Captain Thomas “Trooper” Prentice

5.6.b.1 New England Connections

Captain Thomas “Trooper” Prentice was born in about 1620 in Nazeing, Epping Forest District, Essex, England (1) but the names of his parents is not known. He died on 7 July 1710 (2) in Newton, Middlesex, Massachusetts and is buried in the East Parish Burying Ground (1) alongside his wife in Newton. On 8 July 1647 in Earls Colne (3) he married Grace Bull and they immigrated together to Cambridge, Massachusetts, arriving in 1638. In 1688 they were living in Newton, Massachusetts. He may be the man named Thomas Prentice who was named in the 1638 will of Lt. Colonel Roger Harlakenden. The other man named is a still unidentified man named “Goldinge”. Captain Prentice died of smallpox and left a daughter Grace who married Captain Thomas Olliver (1645-1715).

Thomas Prentice and Grace Bull had the following children: (2)

Grace Prentice

Thomas Prentice

Elizabeth Prentice – She married a man named Aldridge

Mary Prentice

Henry Prentice

John Prentice

John Prentice

Hannah Prentice

WikiTree has some additional information about him:

“Thomas Prentice was born probably between 1621-1621 in England. He married Grace Bull on 8 July 1647 in Earls Colne, Essex, England. One of the couple's children was Thomas Prentice. He was the famous Capt. Thomas Prentice, of King Phillip's war. Emigrated to the colonies in 1648. Thomas is supposed to have learned the art of war with Lt. Col. Roger Harlakenden in Cromwell's army. In his will, Lt. Col. Harlakenden gave 30 [pounds?] to Thomas, at the time of his death from smallpox, in 1638.”

This information is obviously incorrect. Captain Thomas Prentice of King Philip’s War was not the son of Thomas Prentice and Grace Bull because he was that same person. Thomas Prentice was not traveling with Lt. Col. Harlakenden but he may have been in some way related to Roger Harlakenden.

“The earliest record of his being in this country, is the birth of his son Thomas and daughter Elizabeth, (twins,) 22.11.1649. This doubtless means Jan. 22, 1650. The Rev. Jonathan Mitchell's list of First Church of Cambridge members, states that "Thomas Prentice and Grace his wife, and daughter Grace, baptized in England, and about one years old at her parents' joining." This daughter Grace married Capt. Thomas Oliver, in 1667, and died in 1681, ae. 33, therefore born in 1648. At her birth and baptism they were in England. At the birth of Thomas and Grace, they were in this country. They probably came in 1648 or 1649. Mitchell's list also states that their children, Thomas, Elizabeth, Mary and John, were baptized at the First Church of Cambridge. They joined in 1652, and he took the Freeman's oath same year. He settled at the easterly part of Cambridge Village. His house was near the spot where the house of Harbach now stands. In 1653, he hired Gov. Haynes' farm, in the s. w. part of Newton; and according to the deeds, he occupied part of it in 1694. In 1656, he was chosen Lieut. of the company of Troopers, in the lower Middlesex division, and in 1662, Capt. He was chosen one of the Deputies (Representative) from Cambridge to the General Court, in 1672, '73 and '74; and Chairman of the first board of Selectmen of New Cambridge, in 1679, and for many years after. "He and his troop of horse were a terro to the Indians by his sudden attacks and impetuous charges." He was appointed captain of the troop of horse in the Indian war, 24 Jun 1675, and was in the Narragansett fight and aided to its success. In that year he was one of the commissioners to put the captive Indian children to service. He was a friend and counsellor of the converted Indians who, in 1681, petitioned the General Court "that Capt. Thomas Prentice may be appointed their overseer and magistrate." In 1675, Capt. Prentice bought 85 acres of land on the south side of the Charles River in Cambridge, bounded by the two brothers, James and Thomas Prentice the 2nd. He eventually moved his family from Cambridge to Newton, MA; his residence was in the easterly part of Newton where the Boston water works tunnel passed, and near where Harbeck's house stood in 1855. In 1653 he hired Mr. Haynes farm; Haynes was likely John Haynes, Lt. Governor of Massachusetts who married Mabel, sister of Roger Harlakenden. He administered on the estate of Robert Prentice, of Roxbury., who died in 1665; and from his inventory it appears that some of Robert's property was in Capt. Prentice's possession, which facts lead us to believe that they were related to each other.

In 1705 he settled his estate himself by gift deeds, one to his grandson Thomas Prentice, of a house and land in Newton, and one to his grandson, Samuel Prentice of his mansion house and 100 acres of land in the southerly part of Newton. Thomas died at the age of 85 on Sunday, 7 July 1710 in consequence of a fall from his horse on returning from church. He was buried under arms by the company of troop 8 Jul 1710 in the old burying ground in Newton, Middlesex, Massachusetts.” (4)

There is a similar narrative on Prentis.net.

“CAPT. THOMAS PRENTICE was born in England, in 1620 or 1621. The earliest record of his being in this country, is the birth of his son Thomas and daughter Elizabeth, (twins,) 22.11.1649. This doubtless means Jan. 22, 1650. The Rev. Jonathan Mitchell's list of Camb. Church members, states that "Thomas Prentice and Grace his wife, and daughter Grace, baptised in England, and about our years old at her parents' joining." This daughter Grace married Capt. Thomas Oliver, in 1667, and died in 1681, ae. 33, therefore born in 1648. At her birth and baptism they were in England. At the birth of Thomas and Grace, they were in this country. They probably came in 1648 or 1649. Mitchell's list also states that their children, Thomas, Elizabeth, Mary and John, were baptised at the Camb. Church. They joined in 1652, and he took the Freeman's oath same year. He settled at the easterly part of Camb. Village. His house was near the spot where the house of Harbach now stands. In 1653, he hired Gov. Haynes' farm, in the s. w. part of Newton; and according to the deeds, he occupied part of it in 1694. In 1656, he was chosen Lieut. of the company of Troopers, in the lower Middlesex division, and in 1662, Capt. He was chosen one of the Deputies (Representative) from Camb. to the General Court, in 1672, '73 and '74; and Chairman of the first board of Selectmen of New Camb., in 1679, and for many years after. He administered on the estate of Robert Prentice, of Rox., who died in 1665; and from his inventory it appears that some of Robert's property was in Capt. Prentice's possession, which facts lead us to believe that they were related to each other.

Capt. Prentice purchased three hundred acres of land in the Pequod country, bounded w. by L. I. Sound, and N. E. by the College land. Two hundred and thirty acres of this tract is probably the same that was appraised in his son Thomas' inventory, (1685,) at £109, and on which Thomas, Jr.'s son, Samuel Prentice, settled, in Stonington, Conn., about 1710. In 1663, he purchased eighty-five acres of land in the easterly part of Camb. Village, adjoining the land of John Ward. This was his homestead for upwards of fifty years. He was a proprietor in the Camb. lands, and also in the Billerica lands, where he had a division of one hundred and fifty acres, in 1652.

In the will of Roger Harlakenden, dated 1638, there are some small bequests to his domestics, among whom was Thomas Prentice (and Goldinge). If this was our Capt. Thomas, which is probable, he doubtless came to this country with Harlakenden, and returned after his death, in 1638.” (5)

If Captain Prentice was born in 1620 or 1621 in England and came over with Lt. Col. Roger Harlakenden, he would have been only eighteen or nineteen years old at the time of Harlakenden’s death in 1638. Captain Prentice participated in the English Civil War, but it wasn’t with Harlakenden. The English Civil War was a series of civil wars and political machinations between Royalists and Parliamentarians in the Kingdom of England that took place from 1642 to 1651. He probably returned to England after Harlakenden’s death, and if the tradition is true, was one of Cromwell’s guards.

This excerpt is from Celebration of the two hundredth anniversary of the naming of Worcester : October 14 and 15, 1884, p 124:

"Captain Thomas Prentice was born in England in the year 1620, came to this country with his wife Grace in 1649, joined the church at Cambridge and became a freeman in 1652, first settling in Cambridge on the south side of the Charles River in what was then called Cambridge Village, now Newton. He was a farmer. In 1653 he hired Governor John Haynes's farm located in the southwest portion of Newton, occupying a part of the same farm in 1694. As early as 1656 he was chosen Lieutenant of a company of Troopers in the lower Middlesex division. In 1662 was captain, and chosen representative from Cambridge in 1672 and two successive years Chairman of the Board of Selectmen of New Cambridge in 1679 and for many years afterward... Captain Prentice was one of the most skillful among the Indian fighters, and became noted for courage, self-possession and a keen sense of justice. While he was a terror to his Indian foes he was their friend when at peace. He was always ready to respond to the call of the Council and his company was one of the first to march for the protection of the frontier settlements at the outbreak of the war with King Philip, all through which contest he served with great distinction. When Sir Edmund Andros escaped Rhode Island in 1689 and was arrested at Bristol, Captain Prentice was placed in command of the troops to escort him as a prisoner back to Boston. In the year 1689 he was appointed Justice of the Peace and at the death of Major General Gookin the Christian Indians petitioned the General Court to have Capt. Prentice appointed his successor as their Superintendent, he having been in command of the troops that escorted them to Deer Island in 1675. He died July 7, 1709 at the age of 89 years, from the effect of a fall from his horse." (6)

This General Gookin was Major General Daniel Gookin, who originally immigrated to Virginia with his family and later went to Massachusetts where he was one of the founders of Worcester.

A BIO OF MAJ. GEN. DANIEL GOOKIN, by Laurence Overmire, May 2007:

"Major General Daniel Gookin was destined to become a distinguished figure in American history, Daniel probably grew up in Ireland where his father had business interests and immigrated to Virginia with him in 1621. Daniel's first wife is unknown. He married Mary Dolling in London in 1639. In 1641, he again returned to Virginia with his brother John, possibly pushed out of Ireland by the Irish Rebellion. He moved to Maryland in 1643, found the papist rule there incompatible and arrived in Boston May 20, 1644. In 1648, the family moved to Cambridge, where he became a prominent member of the colony. Highly educated, Daniel is believed to have been a scholar of Hebrew. As commissioner to the Indians, Gookin worked to protect them from persecution.

He was Commissioner to the Indians in 1656 and was appointed Major General and Commander in Chief of all the Military Forces of the Colony in 1681." (7)

More information is confirmed about Captain Prentice on the same page at Prentis.net:

“There is a tradition that Capt. Prentice, James Prentice, and Thomas Prentice, 2d, of Cambridge Village were in Cromwell's army, and belonged to his body guard. If Capt. Prentice was in Cromwell's army, it must have been previous to 1648-9. Cromwell turned Parliament out of doors in April, 1653, and died in Sept. 1658. It can be shown from records here, that Capt. Prentice was in this country during all those five and a half years, and onward to the end of his life; and if he were in Harlakenden's family, he probably came over with him in 1635, then fifteen years old. In the same ship came Capt. George Cook, whom we know went back and joined Cromwell's army.

Harlakenden was himself a Lieut. Col. In such company it would be very natural to conclude that Prentice imbibed some of the military spirit he so brilliantly developed during 'Philip's war, which broke out in June, 1675. Six companies of troops were raised in Massachusetts to prosecute that war. On the 26th of June, a company of Foot, under Capt. Henchman, of Boston, and a company of Horse, under Capt. Prentice, of Cambridge Village, marched towards Mount Hope. On the 28th they arrived at the Rev. Mr. Miles' house, in Swanzey, and within a quarter of a mile of the bridge leading into Philip's lands. Twelve of the troopers immediately rode over the bridge for discovery, within the enemy's territories. They were fired upon by a party of Indians, who were concealed in the bushes, killing William Hammond, and wounding Corporal Belcher. The troopers returned the fire and the Indians fled. The next day, (29th,) they reconnoitred Mount Hope, and found that Philip and his Indians bad retreated to the east side of Taunton river. The night following Capt. Prentice's troop retired to Rehoboth, about six miles distant, to lodge for the night; as they returned to Swanzey the next morning, Capt. Prentice divided his company, giving half his men to his Lieut. Oakes, and keeping the other half himself, each taking different routes, the more effectually to scour the country and capture the enemy. Capt. Prentice discovered a party of Indians burning a house, to which he gave chase, and they fled into a swamp. Lieut. Oakes' party had a like discovery. They fell in with some Indians upon a plain, gave chase to them, and killed four or five, one of which was known to be Thebe, a sachem of Mount Hope, and another was one of Philip's chiefs. In this affair, Lieut. Oakes lost one man, John Druce, who was mortally wounded, to the great grief of his companions; he was brought home to his house, near the bounds of Cambridge Village, and died the next day. Previous to his death he made a will, by word of mouth, in the presence of Joseph Dudley, Esq., and requested that Capt. Prentice should see that his will was executed. John Druce was the son of Vincent Druce, one of the early settlers of Cambridge Village.

On the 16th of Dec., Capt. Prentice received advice that the Indians had burnt Jeremiah Ball's house, at Narragansett, and killed eighteen persons, men, women and children, who were sheltered within. He immediately marched in pursuit, overtook and killed ten Indians, captured fifty-five, and burnt one hundred and fifty wigwams, with the loss of four men killed and four wounded. On the 21st of Jan., 1676, Capt. Prentice's company of Troop, being in advance of the Infantry, met with a party of Indians, captured two and killed nine. On the 18th of April, 1676, the Indians made a vigorous attack on Sudbury. Capt. Wadsworth's and Capt. Brocklebank's companies fought bravely in defence of the place, but were overpowered; a remnant of their men took refuge in a mill. The alarm was given and reached Capt. Prentice, who started immediately for Sudbury, with as many troopers as could readily be notified. The men in the mill fought the Indians until night, and were rescued by Capt. Prentice, who rode into the town at great speed, having but few troopers that could hold way with him. He was soon reinforced by Capt. Crowell, from Quabog, with thirty Dragoons.

Capt. Prentice's presence and bravery contributed largely to check the progress of Philip's troops, and he rendered invaluable services throughout the war. He was constantly on the alert, and by his bold and rapid marches, put the enemy to flight wherever he went. His name had become a terror to the hostile Indians. After Philip was slain, terms of peace were offered, in July, 1676, and a pardon to all Indians who would come in and surrender themselves. A Nipnut sachem, called John, with a number of his men, came in, and they were given in charge of Capt. Prentice, who kept them at his house for some time.

Capt. Prentice had been an officer of the company of Troop about twenty years when Philip's war broke out, at which time he was 55 years old. That he was hardy, athletic, and robust, and of unbounded courage, we may safely conclude. It is said that a servant of his was attacked by a bear, in haying time, add kept the animal at bay with a pitchfork, until the old Capt. hastened to his assistance with an axe, and killed the bear outright.

During Philip's war, the Indian converts discovered unshaken fidelity to the English; neither the persuasions, promises, nor threats of their hostile countrymen could draw them from their allegiance to the English. They suffered much by their peculiar position, both from their own countrymen and from the prejudice entertained against them by many of the English. In consequence of the prevalent excitement and their dangerous position, the General Court passed an order, at the breaking out of the war, for the immediate removal of the Natick Indians to Deer Island, in Boston harbor; and Capt. Prentice was appointed by the Court to superintend their removal, with a party of Horse. He took a few men and five or six carts, to carry away such commodities as would be indispensable for their comfort. When he arrived at Natick, to enter upon that service, he made known to them the order of the General Court, and they sadly but quietly submitted, and were soon ready to follow him. Their number was about two hundred, including men, women and children. They were ordered to the Pines, a place on the southerly bank of Charles river, about one mile above the great Cambridge bridge, where boats were in readiness to take them to the Island. After the war, they were removed from the Island, and landed near the same place where they had embarked, and where a temporary residence was afforded them, on the lands of Thomas Oliver, Esq., where they found convenient employment by fishing. The Winter of 1676-7 being past, they returned to their old settlements at Natick, and other places." (5)

This Thomas Oliver was probably the son-in-law of Captain Prentice. Thomas Prentice and Grace Bull had a daughter Grace who was born in England in 1648 and married on 27 November 1667 Captain Thomas Oliver, the son of Rev. John Olliver and the grandson of Elder Thomas Oliver who came to New England in 1631. She died on 30 September 1681 and he married for the second time to Mary, the daughter of Nathaniel Wilson. (6)

Grace Prentice and Captain Thomas Oliver had a number of children:

Grace Oliver, b. 15 Nov. 1668; d. 16 Nov. 1680.

Elizabeth Oliver, b. 11 April 1670; d. 22 June 1674.

Thomas Oliver, d. 22 May 1683.

John Oliver, b. 22 Nov. 1671; d. 20 Dec. 1673.

Hannah Oliver, b. 16 Aug 1674.

Peter Oliver, b. ?

Thomas Oliver, b. 22 July 1676.

Samuel Oliver, b. 18 May 1679; d. 3 Dec. 1729.

Thomas Oliver (twin), b. 22 Jan. 1650.

Elizabeth Oliver (twin), b. 22 Jan. 1650; m. 4 May 1675, Thomas Aldrich of Dedham; she d. 5 Feb. 1676.

Mary Oliver; possibly m. Joseph Stanton (b. 1646 in Hartford, Connecticut; d. 1714).

John Oliver, b. 2 Feb. 1654; d. 1655.

John Oliver, b. 10 July 1655.

Hannah Oliver, b. 1661. (6)

Oliver in Massachusetts and Virginia

I have two lines of Oliver or Olliver in my database. The first is the line of descent through Captain Thomas Oliver who married Grace Prentice, the daughter of Captain Prentice and the second is the line of a ship Captain named Edward Olliver who brought “Thomas Goldinge and Dorothy” to Virginia. This man was from Dallington, Sussex. Are they related? Probably not.

CAPTAIN THOMAS OLLIVER of Boston

1 Captain Thomas OLLIVER b: 12 Dec 1645 in Boston, Suffolk, Massachusetts, USA, d: 01 Nov 1715 in Boston, Suffolk, Massachusetts, USA + Grace Prentice b: 1648 in England, m: 27 Nov 1667 in Cambridge, Middlesex, Massachusetts, USA, d: 31 Jul 1681 in Newton, Middlesex, Massachusetts, USA + Mary Wilson b: 22 Jun 1661 in Roxbury, Suffolk, Massachusetts, USA, m: 19 Apr 1682 in Newton, Middlesex, Massachusetts, USA, d: 02 Dec 1729 in Groton, Middlesex, Massachusetts, USA

...2 Abigail Olliver b: 25 Mar 1697 in Cambridge, Middlesex, Massachusetts, USA, d: 13 Sep 1765 in Groton, Middlesex, Massachusetts, USA + Benjamin PRESCOTT b: 04 Jan 1696 in Groton, Middlesex, Massachusetts, USA, m: 1718 in Massachusetts, USA, d: 03 Aug 1738 in Groton, Middlesex, Massachusetts, USA

There is a line of Olliver from Dallington in Sussex who were connected to Thomas Goldinge, but I have not connected this line with Captain Thomas Olliver of Boston.

1 Edward "of Dallington" OLLIVER b: 1558 in Dallington, Sussex, England, d: Abt. 1610 in Dallington, Sussex, England + Annis Person b: 1558 in Dallington, Sussex, England, m: 1573 in Catfield, Norfolk, England

...2 Annis or Agnes Olliver b: 1584 in Dallington, Sussex, England + Thomas Goldinge b: 1577 in Warbleton, Sussex, England, m: 11 Sep 1610 in Dallington, Sussex, England, d: Abt. 1631 in Herstmonceaux, Sussex, England + First husband

...2 Captain Edward OLLIVER b: Abt. 1590 in Dallington, Sussex, England, d: Aft. 1639 + Annis Greenyer b: Abt. 1584 in Dallington, Sussex, England, m: 28 Sep 1602 in Dallington, Sussex, England, d: Abt. 1650. He was probably the ship Captain who transported Thomas Goldinge and Dorothy to Virginia.

......3 Freegift Olliver b: Abt. 1590 in Dallington, Sussex, England, d: 09 Jan 1619 in Dallington, Sussex, England + Thomas Wayte VIGOR b: 17 Nov 1580 in Bexhill, Sussex, England, m: 20 Jun 1614 in Dallington, Sussex, England, d: 06 Jun 1660 in Dallington, Sussex, England

The question is whether or not there was any correlation between the two families. See Gaulding Origins: Two Lines of the Olliver Family: Are They Related?

Works Cited

1. Thomas Prentice. Find a Grave. [Online] https://www.findagrave.com/memorial/7104445/thomas-prentice.

2. North American Family Histories, 1500-2000. Ancestry.com. [Online] https://www.ancestry.com/search/collections/61157/records/1739714.

3. Essex, England, Church of England Baptisms, Marriages and Burials, 1538-1812. Ancestry.com. [Online] https://www.ancestry.com/search/collections/61698/records/1370603.

4. Captain Thomas Prentice. WikiTree. [Online] https://www.wikitree.com/wiki/Prentice-24.

5. Captain Thomas Prentice. Prentis.net. [Online]

6. Celebration of the two hundredth anniversary of the naming of Worchester. Ancestry.com. [Online] 1884. https://www.ancestry.com/imageviewer/collections/21558/images/dvm_LocHist007389-00069-0?pId=40.

7. General Daniel Gookin. Find a Grave. [Online] https://www.findagrave.com/memorial/43209244/daniel-gookin.

8. Capt. Thomas Prentice of Cambridge, First Generation. Prentice.com. [Online] https://www.ancestry.com/mediaui-viewer/collection/1030/tree/120903483/person/372318083