The Contentious Life of James Wakelee

The first thing I learned as an amateur genealogist is that working on your family history is a work in progress.  Missing documents, contradictory information, unreadable dates, faded records, missing pages, wrong assumptions, bad leads, fading memories of relatives, and other missing links may hamper your progress towards compiling a complete history.  The second, and most important thing I learned has continued to sustain my endeavors ever since.   I learned that even an incomplete picture is much better than being in complete darkness about your family history and heritage.  With this in mind, let’s start unraveling the Wakelee family history, since they came to America around 1636.

Depending on the person who was the scribe for official documents (last will, land records, church, and court documents), or in family histories both published, and unpublished, the family name has been variously spelled as Waklee, Wakelee, Wakeley, Wakelyn, Wakly, Wakely, Wakelin, Waklin, Wiekle, Wakeline, Wackle, Wachleas, Wackla, Whackleass, Wackles, Walkley, and Walkeley.  I encountered all these different spellings, but Wakelee was what my ancestors used for the first 8 generations in America, before it was modernized to Wakeley by my great great grandfather, Ebenezer Wakeley, Jr.  

Two of the main resources used in deciphering the Wakelee story come from two unpublished family histories.  My great-great grandfather, Ebenezer Wakeley, Jr., wrote a manuscript in 1911 titled, “Memorandum of Comrade E. Wakeley’s Family History Since They Were Known in America”. (1)  My great grandfather Ebenezer “Eben” Stone Wakeley wrote an unpublished history in 1924 called, “The Wakeley Family: 1639-1924″.  The “Memorandum” begins the Wakelee family history in America with Henry Wakelee, born about 1620, in England, and died in Stratford, CT, 11 July 1689, while Eben’s research led him to Richard Wakelee, born about 1632, in England, and died in Haddam, CT, 8 Aug 1681.  I’m sure they both made valid assumptions based on information they had on hand at the time of their respective works, but I believe a truer sense of the Wakelee American founder can be found in the genealogical history written by Historian Donald Lines Jacobus.

Donald Lines Jacobus wrote a three volume book titled, “History and Genealogy of the Families of Old Fairfield”. (2)  Like my two ancestors, Jacobus understood the confusion about the Wakelee American founder.   From Volume I, page 627, he wrote, “James Wakelee had lands recorded in Hartford, Connecticut, February 1639/1640.  For several years thereafter, his name frequently appears in lawsuits, and he sometimes acted as attorney for others.  He married on October 5, 1652 to Alice, the widow of James Boosey of Wethersfield, and removed there.  He was Constable of Wethersfield, March 1656/1657, served on several juries, 1655-1662.  Before January 1663 he fled from his wife and family to Rhode Island.  In May 1663, Henry Wakelee had a power of attorney from James.  It seems that James forfeited a bond of 150 pounds, which he had given for his appearance, and his housing and land were ordered sold.  He had been accused of a capital crime, presumably witchcraft. 

Attempts by James and Alice to divorce each other were unsuccessful.  She died at Wethersfield, 30 August 1683.  He petitioned in 1681 vainly for the remission of his forfeiture, and is said to have been living in Providence as late as 1690, and we should guess he was born by 1600.  The relationship of James to Henry and Richard Wakelee is not exactly determined, but it is a reasonable guess that they were his sons by an earlier marriage (italics added).”  Don’t you just love genealogy! 

It is not known how many times James Wakelee was married, but obviously Henry and Richard Wakelee were children from a different marriage.  James Wakelee could possibly have also been the father of a Rebecca Wiekle (sic).  The Jacobus history continued on page 627 stating, “Rebecca Wiekle whose marriage April 25 1665 to Ezekiel Sanford (born 1635 in Milford, CT and died 1683 in Fairfield, CT) is recorded in Fairfield, CT.  Supposing she was born about 1645, it is unlikely that she was a daughter to his son Henry who’s only recorded marriage was in 1649.  She could have been a daughter of Henry by an earlier unknown wife, though not mentioned in his will.”  No records survive that disclose the name of James Wakelee’s first wife nor is it known if she traveled to America with James, Henry and Richard.  Records show the Wakelees arriving in America by at least by 1636.  If Rebecca was a child of James in 1645, then this would prove his first wife did make the trip to America, but died soon after her daughter’s birth.

 Along with the Jacobus information, here are some other facts that may define the relationship of James to Henry Wakelee.  The fact that James Wakelee married the 45 year old Alice, widow of James Boosey in 1652 suggests that this is a second marriage for them both.  The 29 year old Henry Wakelee married the 29 year old widow Sarah (Gregory) Burt in 1649.  This may have been Henry’s second marriage (none other found recorded), but this shows a large age difference between James and Henry Wakelee.  The fact that James Wakelee is named as a plaintiff, defendant, jurist, and acted as attorney in many cases between 1644-1662, had land ownership in Hartford, CT as early as 1639, shows James as a man with age, wisdom, and learning.  When he was forced to flee to Rhode Island in 1662, he gave Henry Wakelee his power of attorney.  To me this is more what a father might ask a son to do.  Finally, Henry Wakelee was involved in the Pequot War in 1637, and the follow-up Battle of Mattebeseck for which he was granted land for his service.  James Wakelee is not mentioned as being involved in either encounter, which could possible mean he was considered too old for service.  These may not be smoking guns, but I believe it brings us closer to the Jacobus conclusion that James Wakelee was the father, and Henry Wakelee the son.
As to the origins of James Wakelee not much is known, but according to a distant cousin Bill Wakeley (3), James may be from around Bristol, England.  Bill’s research revealed that in the 1630s most of the settlers who arrived in New England left due to religious persecution.  There were two groups of Puritans.  The first group arrived in New England in the early part of the decade, mostly coming from the Eastern part of England near London.  They sailed from London, and settled in Massachusetts.  In the latter half of the 1630s a smaller group of Puritans arrived in New England, sailing from other parts of England.  Apparently they did not get along well with the earlier colonizers and were not warmly welcomed to Massachusetts, so they settled in Connecticut instead.  With Henry Wakelee fighting in the Pequot War in 1637 and the follow-up battle in 1638, and obtaining land for this service in western Connecticut, this would place the Wakelees arriving with the Puritans from Western England, sailing from Bristol.


The Contentious Life WPA Murals Weth-watermarked-thumb-320x160-367.jpgAs the Jacobus genealogical research shows, James Wakelee was an active, if not sometimes contentious, participant in the communities that he lived.  Wethersfield and Windsor were two of the oldest permanent Connecticut settlements.  Ten adventurers arrived in Wethersfield from Watertown, Mass in late 1634 with another 20 families arriving in 1635.  Conflicts of religious leadership between the Rev. Cotton Mather, and Rev. Thomas Hooker led to strife and separation.  In 1636, Wethersfield received its official name, its first civil officers, and a right to form a separate church.  Home lots, meadows, plains, and field allotments were given based on family size and social status, and this was effectively completed by 1639.  To press the point concerning James Wakelee’s contentious participation in the Wethersfield community, John Demos, in his book “Entertaining Satan: Witchcraft and the Culture of Early New England” (4) wrote about the times and culture that James Wakelee found himself in when he settled in Wethersfield.  The relations of nearby Indians were problematic and deadly.  In April 1637 the Pequot War began with Pequot warriors attacking the Wethersfield settlement killing nine men, two women were taken captive, and the towns cattle slaughtered.  A 120 person expedition, including Henry Wakelee, went downriver in May and killed hundreds of Pequots, thus ending the war.   This constant danger and religious strife led to alienation and contention among the inhabitants.
In the fall of 1639 a dozen families moved off to form the new settlement of Milford.  Others soon left after for New Haven, Guilford, Stratford, and Saybrook.  In 1641, 35 families left Wethersfield led by the Rev. Richard Denton to the New Haven Colony and founded the city of Stamford.  James Wakelee was in the middle of this contention, and seems to have started some of the contention himself.  Demos wrote, (5) “James Wakelee seems to have been a man of considerable wealth and entrepreneurial bent; he was frequently involved in mercantile activities, though later evidence identifies him as a weaver.6  From 1643 to 1663 James Wakelee went to court no less than thirty-seven times (twenty-one as plaintiff, and 16 as defendant).  This total was matched by few of his Connecticut contemporaries; it provides evidence to characterize Wakelee as an extremely contentious man.”      

Wedding Bliss?

Being a ‘contentious’ man even bled into his intimate and personal life.  James Wakelee seems to have been desperate to marry the widow Alice Boosey, because he even brought her to court for a breach of covenant.  It seems she was interested in another gentleman, but forgot to tell Wakelee their engagement was off.  According to Records of the Particular Court of Connecticut, 1639-1663 (7) the lawsuit dated 5 Dec 1650, Hartford, Hartford Co., CT, had James Wakelee as plaintiff and the widow Boosey defendant, in an action of the case for breach of covenants.  The court wrote, “In the action between James Wakely (sic) plaintiff and the widow Boosy (sic) defendant, the Court judgeth that however there appear not enough evidence to prove a contract of marriage between the said parties, yet there is sufficient to evince some engagement or promise of the said Boosy to James Wakely in reference to such a business, and therefore her proceedings with another before a clear disengagement had from the former was at least disorderly.”
The ‘disagreement’ must have finally been settled because it is recorded in Hartford that “Marriage: 5 Oct 1652, Hartford, Hartford Co., CT., James Wakely and Alice Boofy (sic).” (8)  Some dowry must have been promised, because James Wakely went to court 6 Mar 1653.  It is recorded that “James Wakely proved at this Court by Samuel Steele that the wife of the said James hath in the time of her widowhood given a bond to Joseph Boosy of 100 pounds forfeiture if she married to James Wakely.”  Alice made one more attempt to dispute the marriage arrangements as is recorded in April 1653, “This court judges the Deputies action in marring Jeames (sic) Wakely and the widow Boosy to be legal.” (9) After their marriage, James Wakelee purchased the home of Alice’s former husband, and became the stepfather to her four living children, Joseph, Mary, Hannah, and Sarah Boosey.   James Wakelee must have settled in, because his court cases declined considerably (only three cases from 1652-1658).  After almost a decade of uninterrupted residence in Wethersfield, CT the witch hunt fetched up James Wakelee in the latter part of 1662.

Accused of Being a Witch

The Contentious Life Witchcraft 005C-thumb-320x305-369.jpgAccording to John Demos, “The ‘Hartford Controversy’ in the 1650’s embraced Windsor and Wethersfield as well.  Issues were joined in a torrent of petitions and counter petitions.  The General Court contrived elaborate measures to suppress ‘differences’.  Towns quite literally split apart, with dissident groups moving away en masse.  From such fraternal strife it is not a long step to witchcraft and in this regard, as well, Connecticut set the pace for the rest of New England.  Connecticut produced the first known trial for witchcraft anywhere on the North American continent.  Connecticut endured the first witchcraft ‘panic’.  Connecticut appears to have also executed more alleged witches than any other colony, if the Salem outbreak alone be exempted.”  So it was these trying times that found James Wakelee at the mercy of public superstition and religious strife.

James Wakelee was prosecuted, or threatened with prosecution for witchcraft, in 1662, 1665, and 1668.  He fled to Rhode Island sometime before January 1663, but apparently there was a period between these dates when the charges were withdrawn, permitting his temporary return to Wethersfield.  In July 1663, James Wakelee returned to Wethersfield, and the Court ruled  “James Wakeley being present the magistrates do hereby take off the sequestration upon his estate.”  He remained in the area until 1665 and posted a large personal bond for his appearance before the forthcoming session of the court, but he soon fled.  Once the feeling had been aroused, charges pressed, and the court and community mobilized against him, Wakelee was understandably reluctant to return to Wethersfield. 
According to John Demos in his book “Entertaining Satan”, (10) “Most cases, where a male is accused of being a witch, it is because of an association of a female accused of witchcraft.  Guilty by association.  It was also believed that transmission of witchcraft would follow the lines of family or close friendship.”  Some men were accused of witchcraft due to family or neighborhood quarrels.  Instead of a secondary accusation, James Wakelee seemed to qualify as a witch of a primary kind.  Viewed in context, he
was truly an exception.  The rule in early New England was that witches were women. (11)  Witchcraft was itself considered a capital offence, and witches were criminals of a special sort, but approximately one half of the people accused of practicing witchcraft were also charged with the commission of other crimes, especially assaultive speech and theft. (12)  According to colonial records, (13) James Wakelee was a frequent litigant, at least 37 times before his indictment for witchcraft.  His being in public affairs, probably gaining many enemies (including his wife), may have led to this accusation of witchcraft. 
According to the only surviving deposition written 13 Aug 1668, for a 1668 trial of James Wakelee, “Thomas Bracey testified that formerly James Wakeley (sic) would have borrowed a saddle of the said Thomas Bracey, which they said Thomas Bracey denied to lend him.”  The deposition tries to link Wakelee to an accused witch, Katherine Harrison, and accuses him of being one of her confederates.  Bracey recalled various misfortunes that befell him following the quarrel with Wakelee concerning the saddle.  The culmination being a spectral assault, with Wakelee and Harrison appearing at night “by the bedside” and “afflicting and pinching [Bracey] as if his flesh had been pulled from the bone.”  This deposition was taken years after the actual accusations against James Wakelee occurred.  It seems Thomas Bracey held a grudge for a long time about an “exchange of harsh words.”  Wakelee left to Rhode Island for good in 1665, living out a much poorer material life, but the forced exile saved his life.

Life on the Run

In January 1663 the court noted that he [Wakeley] had ‘lately fled’ and ordered that his estate ‘be secured and kept safe’ while two selectmen made an inventory of its contents.  In March ‘the sequestration laid on James Wakeley’s estate was continued until the Court takes it off, though his wife might ‘pay and receive debts’.  By May 1663, Henry Wakelee had a power of attorney for his father.   In July 1663, James Wakelee returned to Wethersfield, and the Court ruled  “James Wakeley being present the magistrates do hereby take off the sequestration upon his estate.”  By 1665 James Wakelee fled to Rhode Island again, this time for good.  Wakelee forfeited the 150 pound bond, which he had given for his appearance, so the court ordered this land be sold to pay the bound.  Alice Wakelee petitioned to reduce the fine to help protect her own interests.  It is recorded that, “Upon the petition of James Wakleys (sic) wife, this court doth remit 50 pounds of the hundred and fifty pounds bond forfeited by James Wakeley (sic) to this Corporation.  This Court doth order the treasure speedily, by virtue of this warrant, to determine so much of the land of James Wakeley as may satisfy a hundred pounds of the bond forfeited to this Corporation by James Wakeley.” 
James Wakelee tried a few times to petition for a release or remittance of the forfeiture of his land.  In 1673, he petitioned the Court of Assistants for an abatement of the forfeiture and renewed his petition in 1682.  The court did not agree, “This Court having heard the petition of James Wakely (sic), for a release or remittance of the forfeiture of his land which he hath long since forfeited, the Court having considered the same and what he hath presented, does not find that he hath given any just reason to the Court to remit any part of the sayd forfeiture of his bond.”
With no luck on the remittance of the forfeiture of his land, he tried to divorce his wife.  In a filling in 1676 at Rhode Island James Wakelee demanded from the Court, “Have his wife sent to him or grant him a bill of divorce.”  Wakelee claimed that Alice Boosey had abrogated her marital vows by refusing to join him.  Alice Wakelee was able to prove to the court’s satisfaction that James Wakelee had engaged in a prenuptial agreement not to remove her from her dwelling in Wethersfield, CT, without her consent.  The Bench announced that it saw no grounds to grant either petition, and furthermore, no cause “so to compel [Alice] to remove” to Rhode Island.
Even in Rhode Island, James Wakelee’s life was not easy.  He seems to have run into trouble being a squatter.  In April 1668, a recorded listing showed recent acts of Rhode Islanders, “Mr. Thomas Stanton had been prohibited from mowing land granted to Mr. Willis, and threatened with the cost of a thousand pounds if he persisted, ‘they take in new comers contrary to order, viz.  Goodwife Seagar, James Waklie (sic), and the tinker.  They sell which is called Province land, and why may we not settle on our own by the same rule.’  Signed, by order of the Town, by John Stanton, Town Recorder.

Contentious to the Last

Alice Wakelee died 30 Aug 1683 in Wethersfield, CT, and it seems that James Wakelee disputed the estate settlement and actually won a judgment.  It was recorded, “Nathaniel Foote, as attorney to James Wakely (sic) of Rhode Island, whereof by way of appeal from the judgment of the Court of Assistants, held at Hartford, May 27, 1690, which action was a plea of the case for truer and conversion, for that he the sayd Standly, on the 6th of Sept., in the 35th year of the reign of our sovereign lord Charles the 2nd, late King of England, did take into his hands and custody a certain sum of money with other goods and chattels, to the value of 107 pounds, 19 shillings, and 4 pence, specified in an inventory exhibited by the sayd Nathaniel Standly to the County Court held at Hartford, Sept 6, afore sayd under the name of an inventory of the estate of Alice Wakely, deceased, which sum of money and other goods and personal estate of him the sayd James, which goods of the sayd Nathaniel Standly hath refused to deliver or the value of them to him the sayd James Wakely or his attorney, to the value of 146 pounds (includes attorney fees).  In which action the jury found that if the deed of gift from Wakely to his wife be good in law, then they find for the present plaintiff one hundred and 10 pounds and cost of court.”
The follow-up court case concludes the issues concerning the estate of Alice Wakely, but it seems James Wakely left this world without seeing any proceeds.  It is recorded that, “Mr. Nathaniel Foote motions this Court that the Marshall might be put upon it to finish the execution he received against Mr. Nathaniel Standly’s estate, for to answer a judgment he obtained against him as he was attorney to James Wakely of Providence, October last: This court grants his request, and appoints the Marshall speedily to issue the same, and to deliver the estate to Nathaniel Foote as administrator to the estate of sayd James Wakely according to judgment.”  James Wakelee died sometime after he received the 1690 judgment for the value of his wife’s estate, and is buried at an unknown location in Providence, Rhode Island.

Some Final Recognition

The Contentious Life founders_monument-thumb-320x768-365.jpgEven though James Wakelee lived on the run accused of witchcraft, leaving behind his wife, friends, and worldly possessions, and died in Providence, Rhode Island in forced exile, he did receive recognition from The Society of the Descendants of the Founders of Hartford, as being a founder of the city.  The ‘Founders Monument’ was erected in the Ancient Burying Ground in 1837, but was updated to durable Connecticut granite in 1986 to commemorate the 350th anniversary of the city.  The east face of the monument starts with “In memory of the First Settlers of Hartford”, and lists 144 founders including James and Henry Wakeley.

Read more about the Wakelee family @

Witchcraft illustration from the Connecticut State Library website.


1  Copy of 41 page manuscript is in possession of author, and can be found in the Genealogy Library at the U.S. Library of Congress.
2  Donald Lines Jacobus, History and Genealogy of the Families of Old Fairfield, Volume 1, 1930 edition, published by Genealogical Publishing Co., Inc., with additions and corrections added in 1976, 1991.  Volume I, pages 627-620 and 722 (index) details the Wakelee family.  Volume II, pages 981-987 continues with the Wakelee family.  Volume III, pages 336-337, details Jonathan Wakelee.
3  E-mail from Bill Wakeley dated June 14, 2001.
4  John Demos, Entertaining Satan: Witchcraft and the Culture of Early New England, Oxford University Press, 1982.
5  Ibid, page 353.
6  Trumbull and Hoadley, editions, Public Records of the Colony of Connecticut, Volume IV, pages 35-36.
7  Records of the Particular Court of Connecticut, 1639-1663, published in Hartford, 1928, page 91.
8  Albert C. Bates, Hartford, Connecticut, Land Records, 1639-1688; Birth, Marriages, and Deaths, 1644-1730, Volume I, Page 608.
9  See Connecticut Public Records.  Check out to see colonial documents, which has an easy to use search engine.  You can review all 37 court proceedings that James Wakelee was involved in.
10  Entertaining Satan, page 60.
11  Ibid, page 62.
12  Ibid, page 77.
13  Records of the Particular Court of Connecticut: 1639-1663, pages 86-87.

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