The surname Lawless is formed from the Old English word laghles meaning an outlaw, it may, as far as Ireland is concerned, be regarded as falling in the Anglo Norman category with the arrival of Sir Hugh de Laighleis.

In the 12th century, Dermot Mac Murrough, King of Leinster, was about to be crushed by Roderick O’Connor the mightiest of Ireland’s Kings. Panic stricken Dermot went to the feet of King Henry 2’nd swearing temporary allegiance.

On the 18th of October, 1172 some hundred ships weighed anchor from Milford Haven (a seaport town on the west coast of Wales), and after a short voyage, glided into the harbor at Waterford. The army of King Henry, on this occasion, consisted of four hundred Knights and several thousand men-at-arms. Amongst the Knights was Sir Hugh de Laighleis of Hoddesdon, County Herford, England. The ancestor of Sir Hugh was David, Duke of Normandy.

No sooner had the Norman Knights set their feet upon the Island, than they at once desired to possess a share of the golden valleys and fertile pasture lands. Henry was desirous of rewarding his faithful Knights, and as he had no land to spare in England, he gladly distributed amongst them the Irish manors which he only knew by name.

Sir Hugh de Laighleis heard of the exquisite scenery of Shanganagh and made a personal pilgrimage to the spot. He asked King Henry to make it his for evermore. His Majesty heard the request, complied with it, and from that moment Shanganagh became the property, or as the attorney said, who drew up the deed of settlement-the “fee simple” of Sir Hugh. The old age of Sir Hugh de Laighleis did find a home in the vale of Shanganagh. He married, erected a castle near the water’s edge, and lived, and died, after “a long life of labor,” within it. The dichotomized ruins of this old castle were still visible and could be observed from a great distance in the later part of the 19th century.

The flat, well wooded tract extending along the coast from Killiney to Bray, including portion of the valley of the Loughlinstown River, is known as the Vale of Shanganagh.  The name Shanganagh, which should be accented on the first syllable, the other two being pronounced very short, means a place abounding in ants, and at the present day these insects are found in great abundance in the district, especially along the sandy banks of the river.

By a very old family escutcheon, which remained in the possession of the Lawless family of Shankhill, we find that Sir Hugh had a son named Richard. Beneath this heraldic devise was an unfurled scroll, bearing the following inscription:-“Sir Hugh Lawles, Knight, sent a deede sealed with his arms, dated ye first yeare of King Edward ye 3rd, unto his son Richard Lawles, of all his lands of ye manor of Shanganagh.” As King Edward III was in his first year as king in 1327 we must conclude that the above was not the original Hugh who came to Ireland in 1172. It would be impossible, with any degree of accuracy, to trace the genealogical descent from Sir Hugh de Laighles, however some names, dates and family connections are available in historical reference books. In a short time the family had built manors, not only near Bray in the vale of Shanganagh, but also in Kilruddery, Corkagh and Old Connacht, all in the Bray area. The castles and fortifications which they built were to defend their lands from the Irish tribesmen in the mountains.

Please note that the ancestors first mentioned here from Sir Hugh (1150) to Robert (1300) are estimated from data found in history books. Starting with Walter Laghles (1350), records are reasonably accurate as they are taken from an old hand written manuscript (descendant chart) located at the National Library of Ireland.  The ancestral chart has 10 generations of the LAWLESS sept from Richard Lawless and his wife Isabella Cottrell, born in the 1400s, to Sir Nicholas Lawless (1733-1799) and his wife, Margaret Browne (1748-1795).

In Ireland, septs were the Irish equivalent to the Scottish Clan in political and economic stature.  Scottish Clans also contained septs or branches, which were founded when powerful or prominent clansmen established their own important families. Clans often had many septs that were often related through marriage. During difficult times, the families sought to ally themselves with larger more powerful clans for protection from enemies and other feuding clans alike. This practice, which often included paying homage to the Clan Chief at important events was effective in building respect, devotion and familiarity between different families within the same clan.  Some septsbecame so powerful that they later became clans in their own right.

Richard De Laighleis was born 1180 in Shanganaugh, Dublin, Ireland.  Shanganagh Castle was located in County Dublin – about 1/4 mile from Shankill.  The first was built by Sir Hugh de Laighleis some time after his arrival in 1172. There were several fortifications and castles built in the valley of Shanganagh by the descendants of Sir Hugh, to defend the lands from mountain tribesmen. One of these castles stood close to the Loughlinstown River. The castle had attached to it a hall, which, although only roofed with thatch, was of considerable dimensions, and round it laid an orchard, garden and ornamental plantations, doubtless extending down to the Loughlinstown River.

image005 (1)Hugh De Laighleis was born in Shanganaugh, Dublin, Ireland.  He had three children: Thomas Laghles, Sir William Laghles, and John Laghles.

Thomas Laghles, was born in Ireland. As early as the year 1285, Thomas Laghles appears on Irish record as constable at Connaught. That same year Sir William Laghles obtained from the Barrets a considerable tract of country in and near the parish of Killala (Co. Mayo). Son of Thomas was Richard.

Richard Laghles was Provost (Mayor) of Dublin between 1310 – 1313. In 1312 Richard Laghles was Provost of Dublin. He is alleged to have averted a famine in the city by his stern and cruel treatment of the bakers. They were found using false weights in dealing with the public. Upon hearing of this injustice, Richard sentenced them to be drawn through the streets, tied to horse’s tails. He had eight children: ‘Sir’ Hugh, Elias, ‘Rev.’ Gerald, Robert, Roger, Simon, ‘Bishop’ Stephen, and William.

Robert Laghles, was born before 1300 and died after 1350. In 1314 the government pardoned the offences of Robert Lawless, and others, due to their service in Offaly and the Leinster mountains.  On April 23, 1350, Peter Howel, Richard fitz Michael Howel, Elias fitz Robert Walsh and Hugh fitz Robert Lawless were part of the assembly to elect Walter Harold as head of his sept. On April 23, 1350, Hugh fitz Robert Lawless and others were part of the assembly to elect Walter Harold as head of his sept. In 1350 we find mention of the Dublin Walshs. They, with the Harolds, Archbolds, Lawlesses and Hackets were posted along the rampart of the Pale, their charge to keep the Byrnes and O’Tooles away from Dublin. His children were Walter, Thomas and William.

Walter Laghles, (1), was born in about 1350 in Ireland. The first of the name to settle in Kilkenny was Walter Lawless, who was admitted as a burgess of the town of Talbot’s Inch in 1396 (now part of Kilkenny City). He had three children: Peter, James, and William.

James Laghles, (2), son of Walter Laghles, was born about 1390 in Ireland.  He had two children: Adam and Richard.

Adam Laghles, (3), son of James Laghles, was born about 1410 in Ireland.  He had two sons: Richard and Patrick.

Richard Lawles, (4), son of Adam Laghles, was born in 1440 in Ireland. He married Isabella Cottrell in Cathedral of St. Canice, Kilkenny, Ireland. She was the daughter of James Cottrell and was born in Ireland. Meantime, branch of the family of Walsh of Carrickmines had settled in the parish, and by degrees the Walshes supplanted the Lawless family. They appear first in 1447 at Shanganagh in the person of Edmund Walsh, to whom the Seigniory of that place was leased in that year by the Vicars Choral of St. Patrick’s Cathedral.  Some twenty-five years later, in 1473, legal proceedings were instituted against Edmund Walsh for refusing to pay rent and continuing to hold the lands after the expiration of his lease, but the dispute was settled, and we find amongst the subsequent owners of Shanganagh, in 1482 Charles Walsh, in 1509 Richard Walsh, and in 1521 Charles, son of Richard Walsh.

From the Lawless family these Townlands passed over to the Walshes, who as “Irish rebels and Papists” are frequently alluded to in the old chronicles of Dublin. Although Shanganagh passed out of the hands of the family, the Lawlesses were too much attached to the old property not to re-establish themselves as soon as possible in its immediate vicinity. They did this by erecting a castle at Shankhill and a dwelling house at Cherrywood- Townlands situated within a stone’s throw of Shanganagh. In the 15th century the Lawlesses were in possession of considerable landed property in `Kilkenny. They had three children: Walter, John, and Richard.

Walter Lawles, (5), son of Richard and Isabella Cottrell Lawles, was born in Ireland.  He was the Portreeve and Burgess of Kilkenny in 1526. He married Leticia Courcy of Ireland.  The ancient city of Kilkenny is situated on the banks of the River Nore with its civil and ecclesiastical roots deep in the past.  St. Canice, after whom the cathedral is named, built a 6th century church on the site now occupied by St. Canice’s. After the Anglo-Norman invasion c1170 the town was granted to Strongbow, Earl of Pembroke. In 1642 the city became the seat of the Confederate Parliament, representing the Irish and Anglo-Norman Catholics, which functioned for 6 yrs. The cathedral had the most magnificent stained glass windows in all Europe. Oliver Cromwell, c1650, came along, smashed the windows and stabled his horses in the cathedral. It was originally the property of the Catholic Church but became Church of England in the 16th or 17th century. In the Cathedral of St. Canice there is an altar tomb slab with Latin inscriptions thereon, of which the following are translations:- “Here lieth Adam Cottrell, James Cottrell, Richard Lawles and Walter Lawles with his wife Letitia Courcy, former Burgesses of the town of Kilkenny and Lords of Talbot’s Inch, which Walter died on the second day of the month of Dec., A.D. 1550, on whose souls may God have mercy. Amen.” “Here lieth Richard Lawles, son and heir of the aforesaid Walter, who died on the 6th day of the month of Oct., A.D. 1553.”  “Here lieth Jas.Lawles, brother and heir of Richard Lawles, son and heir of Walter Lawles, who died the last day of July A.D. 1562, on whose soul may God have mercy. Amen. And Adam Lawles, who died the 20th day of Oct., 1600, and Letitia Shee, his wife, who d. the 5th day of Oct. I believe that my Redeemer liveth, and in the last day I will rise out of the earth, and in my flesh I shall see God my Saviour, whom I myself shall see and not another, and my eyes shall behold.” Job.XIX.,25-7.

Children of Walter and Leticia were: Adam, Richard, James, William and Thomas.

Adam Lawles, (6), son of Walter and Leticia Courcy Lawles, was born about 1540 in Ireland. He was the Port Reeve in Irishtown (in Kilkenny City) in 1564. He married Leticia Shee of Ireland. She died Oct 05, 1576 and he died Oct 20, 1600 in Kilkenny.  Both are buried at St. Canice Cathedral, Kilkenny, Ireland.  They had two children: Leticia and Walter.

Walter Lawless, (7), son of Adam and Leticia Shee Lawles, was born in 1570 in Kilkenny, Ireland.  This Walter Lawless married Margaret Rothe, daughter of Robert Rothe (d. 1619) of Kilkenny. Walter was agent to Thomas Butler, 10th Earl of Ormonde and was also Portreeve of Irishtown in 1605. On the 9th of May, 1608, he obtained from his gracious Majesty, King James the First, the princely grant of seven manors, situated in the counties of Tipperary, Waterford and Kilkenny. According to an old deed of transfer, these manors “possessed the Right of Patronage, and were to be held forever “in capitae” by Knights service.” and died August 6, 1627 in Kilkenny. They had seven children: Richard, Simon, Leticia, Adam, Ellen, Nicholas, and James.

Richard Lawless, (8) son of Walter and Margaret Rothe Lawless, was born about 1600 in Kilkenny. In 1648 during the civil war under King Charles I., he was Procurator of the Supreme Council of the Confederate Catholics of Ireland. In this capacity he greatly distinguished himself by opposing the massacre of Kilkenny Protestants, when proposed to the Council by Torlogh Ogr O’Neil. Torlogh petitioned the Council that all English Protestants there should be put to death, whereupon Alderman Richard Lawless answered that they were all robbed before and he saw no cause that they should lose their lives. In 1635, he married Ellen/Maud Shee, daughter of Lucas and Ellen Butler Shee of Kilkenny.  She was the born in about 1600 in Kilkenny. He later married Margaret Denn, daughter of Patrick Denn, in 1641. She was born about 1600 in Grenan, County Kilkenny. Richard died in 1663 in County Kilkenny. His will was dated Sept. 8, 1662 and proved July 22, 1663. Margaret was named in his will and died after 1670.  From his first marriage, they had one child: William. From the second wife they had five children:Walter, Adam, James, Mary, and Thomas.

Archer, Rothe, Shee, Lawless, Langton, Ragget, Archdekin, Knaresborough, Cowley & Butler families were the prominent old families of Kilkenny who were mainly of Norman descent. They became wealthy merchants, and became known as the “Ten tribes of Kilkenny”. There was much inter marriage between all these families. This kinship strategy was characteristic of all the major families in Tipperary, Kilkenny and elsewhere, revealing the interweaving of ‘Gaelic’ and ‘feudal’ strategies of land management and social control. The old medieval part of Kilkenny was built by these families. They were quite wealthy, some very well educated and cultured. Of the so-called Ten Tribes of Kilkenny the Shees (the only ones of Milesian blood), were the most influential; the Rothes and the Archers were next in importance. County Kilkenny was dominated up to the 1640’s by a long established territorial, political and social hierarchy headed by the earl of Ormond, who directly ruled over 50,000 plantation acres.  They lost much of their property and possessions in the 1600s, particularly during the Cromwellian era when their lands were confiscated.

In the mid 1500’s, the Anglican Church (The Church of England) came into existence, breaking away from the Catholic Church and causing much blood shed and strife. The Throne of England was also split between Catholic and Protestant. After the Restoration, James II, a Catholic, had succeeded his brother Charles II as King.  James’ autocratic and pro-Catholic policies soon provoked English politicians to invite the King’s own son-in-law, the Dutch Prince William of Orange (later William III of England) to replace him as king. Those who followed James came to be known as the Jacobite Army and those who followed Prince William were called Williamites. It was during this period that Walter Lawless was born.

Walter Lawless, (9), also known as Captain Walter Lawless, son of Richard and Margaret Denn Lawless, was born about 1642, in Kilkenny.  He was the High Sheriff of County Kilkenny.

On the flight of James II from Ireland to France, the Earl of Tyconnel summoned the Irish Loyalists and commanded them to arm in defense of their lawful Sovereign. The Battle of the Boyne: The Army in Ireland was totally reorganized by Richard Talbot, Earl of Tyrconnell when he was appointed Lord Deputy in Ireland. Tyrconnell transformed the almost exclusively Protestant Irish Army into a predominantly Catholic force of around 8,000 men. After the Glorious Revolution in England in 1689 he then expanded this army to around 45,000 men almost all Catholics. It was down to about 35,000 by the time of the Battle of the Boyne. Schomberg’s Williamite army by contrast was made up largely of English troops with Anglo-Irish officers (Protestants). It also had 2 Dutch Protestant infantry battalions and 4 French Huguenot regiments and later some Swiss ones. The local Irish contingent was just 6,000 Ulster Protestants organized in 9 regiments. Although the Battle of the Boyne still gets all the press coverage, the real conflict that decided things was at Aughrim in 1691, a scene of incredible carnage.  Walter Lawless served with Henry Luttrell’s Horse Regiment. Even though they fought bravely, the war was lost. The Williamite’s now had the problem of quickly eradicating an entire hostile army from Ireland. The Treaty of Limerick in October 1692 provided for the transport of the Irish Catholic army to France (11,000 sailed away, 2000 remained in Ireland and 1000 choose to join William’s army). As part of the agreement, they had to leave the Kingdom (England, Scotland and Ireland) or be put to death. The Williamite victory in Ireland was followed by the confiscation of most ‘Jacobite’ estates. Forfeited estates of Kilkenny Jacobites in 1702 included those of Henry Archer, Edmund Blanchfield, Walter Bryan, James Bolger, Edward Fitzgerald, Viscount Piers Galmoy, John Grace, Richard Grace, Robert Grace Jr., John Larkan, Walter Lawless, Charles Ryan, and Robert Walsh. If they ended up with property, it was only a fraction of their original holdings. If they remained Catholic after this time, their descendants ended up in poverty; if they became Protestant (Church of Ireland) then they retained some property and were fairly prosperous. Anyone listed as Jacobites were exiled from Ireland to North America, Canada or France. The Lawless families were nearly all staunch Jacobites. It is also said that between 1690 and 1730 some 120,000 people left Ireland. This time would forever be remembered as ‘The Flight of the Wild Geese’.

Captain Walter Lawless married Anne Bryan, daughter John Bryan of Jenkinstown, County Kilkenny. Walter and Anne had 5 sons. The eldest, Richard, fell at the seige of Limerick in 1691. Patrick Lawless, the second son, was taken prisoner at Aughrim. He later served with distinction in the armies of his Spanish Majesty, was appointed, during the Orleans Regency, Ambassador Extraordinary to the Court of France, created Knight of the Equestrian Order and finally, inaugurated Gov. of Majorca, which office he continued to fill, with honour and reputation until his death. The third son, John Lawless, having manifested strong feelings of loyalty towards James II, was attainted at the same time as his father, Capt. Walter Lawless and was reduced to poverty. The two younger sons, James and Thomas, died before reaching their majority.

Richard Lawless, (10), son of Walter and Ann Bryon Lawless, was born about 1655 in Kilkenny, Ireland. He was killed at the Battle Of Aughrim in 1691. The site of this battle was Kilcommadan or Aughrim Hill – which stretches south-eastward from the ruined castle and village of Aughrim. The Williamite army moved forward from Athlone on 11th July 1691. The next day there was skirmishing as it came into contact with the Jacobite outposts. Patrick Sarsfield and a combined French and Irish army were routed at the Battle of Aughrim in July of 1691, in one of the most significant battles in Irish history. Following the battle, and the defeat at the siege of Limerick, most of the old Gaelic aristocracy left the country for service in France in what has been called “the Flight of the Wild Geese.”

Richard’s children (his wife Anne is never mentioned), left Dublin and arrived in Virginia in April, 1694. His children were: James, Nicholas, Walter, Cornelius, Patrick, and Michael.

James Lawless, (11), son of Richard Lawless, was born about 1675 in Kilkenny, Ireland. He married Elizabeth Dempsey in 1699 in Essex (later Caroline) County, Virginia. She was born in 1678. Elizabeth Demsey was a white slave during the 1690’s of the Essex planter, Wm. Leake, who had the county court extend her indenture in 1696 for another year because she had given birth to a bastard. Another extension in 1697 stipulated that she must remain in the service of Leake until she attained the age of 21. That birthday came in 1699 when Leake’s neighbor, Jas. Boughan, transported both James Lawless and Elizabeth. Dem(p)sey into Essex County where, of course, they already lived. At the time of the 2n’d hearing, the court ruled that Thos. Butler Dem(p)sey was also bound unto Wm. Leake until age 21 and that Leake must give the lad a year of schooling. Boughan transported them again in 1700. James died after 1725 and Elizabeth died after 1741. They had five sons: Henry, William, Michael, Benjamin, and James.

At this point we could look at each of the five sons and trace all their descendants as well. All the information that could be obtained would not be able to fit in the volume of one book. I will include a description of Henry, William, Michael, Benjamin, and James. From there we will follow just William, our direct ancestor, and John Lawless, his son.

Henry Lawless, (12), son of James and Elizabeth Demsey Lawless, was born about 1705 in Essex (later Caroline) County, Virginia. He was probably married, but the name of his wife is unknown. Henry Lawless appears in the records of Caroline County for the first time in 1743 when he had to be in court because his slave Phill was being tried, was found guilty, and sentenced to death for burning the residence and various other buildings belonging to Thos. Emerson. Present were Elizabeth Lawless (his mother), Geo. Hoomes (noted in his dealings with Henry’s purported brother Jas. Lawless II) and John Taliaferro (1687-1744), the uncle of Dr. John Taliaferro who was to marry Mary Hardin, the sister in law of Henry Lawless’s presumed nephew, Jas. Lawless III. Henry Lawless was ordered by the court on 13 Dec 1745 to pay Benjamin Lawless 125 pounds of tobacco for his attendance for 5 days at a trial to give evidence against the plaintiff Edw. Crowley who, like Benjamin, may have subsequently moved to Pittsylvania Co. where Crowleys abounded; Wm. Jeter gave evidence against Henry in this case of trespass. Wm. Jeter is noted in association with Jas. Lawless II whose purported grandson Jas. Lawless married Wm. Jeter’s grandniece Catherine in Georgia. On 14 June 1746, Jas. Lawless II acknowledged “his deeds and lease and release” to Henry Lawless.

Henry Lawless was a member of the famous expedition of Dr. Thomas Walker (1715-1794) in 1750 through the Cumberland Gap to explore Kentucky. This safari is said to have discovered the Lawless River Valley. The James Walker with land adjacent to the Clay, Wilson, and Lawless property in the Fall Creek region of Pittsylvania County is reputed to have been a son of Dr. Walker. On the expedition of 1750 were also Wm. Tomlinson, Ambrose Powell, John Hughes, and Colby Chew. Ambrose Powell was probably from the Powell Family of Port Royal where Michael Lawless, possibly Henry’s uncle, added to his land in 1713.

The last mention of Henry Lawless in the Caroline records was on 14 Sept 1750 when the court took notice that he had acknowledged his deed and indented to Thos. Samuel. Henry undoubtedly played a role in the removal of the Lawlesses, Taliaferros, Hardins, and Lynches westward just after King George’s War (1740-1748) but before the French and Indian War (1754-1756).
image006 (1)Henry was evidently living in Augusta County and producing tobacco there by the time Dr. Walker became the governor of this vast frontier wilderness in 1752. Following the devastation wrought by the Indians on the white settlements in the Roanoke River region, Colby Chew was again with Henry Lawless in 1756 in the retaliatory expedition to the Sandy Creek region where Benjamin Lawless, Sr., had acquired his first Halifax (later Pittsylvania) property the previous year.
Indians killed Henry Lawless in a battle on 14 May 1757 in Augusta County, Virginia on the Jackson River some 30 miles west of what is now Lexington and 15 miles west of the current boundary of Rockbridge County. He evidently died intestate. Nothing about his estate has surfaced in the Halifax (or Pittsylvania) records, although the Halifax court orders, deeds, and estate records, including loose papers, need to be examined. The administrator of his estate was Adam Dickinson, undoubtedly from the Dickinson Family of Caroline and perhaps with relatives among the Dickinsons of Pittsylvania and its offspring Patrick Co.. In the administration of his estate, about half of Henry’s indebtedness of just over 27 pounds was to Dr. Thos. Walker. It is possible that he had a son Richard in Amherst Co., VA.
William Lawless, (12), son of James and Elizabeth Demsey Lawless, was born about 1710 in Essex (later Caroline) County, Virginia. He first appears in the records in Goochland Co., VA where he witnessed the will of a Matthew Cox 15 Jan 1733. Also witnessing was Robert Carter who joined John Bolling and Benjamin Harrison in also witnessing a conveyance of 400 acres on the south side of the James River 4 Nov 1732 by Ashford Hughes to Wm. Dillon. From John Bolling’s family undoubtedly came the Thos. Bolling to who was bound Wm. Lawless’ grandson Wm. III in 1786. From Wm. Dillon’s family undoubtedly came the Sarah Dillon who married Wm. Lawless I’s son Augustine Lawless. Unfortunately, no estate papers have surfaced for William Lawless, although on Oct 05, 1777 he sold 133 acres in Cumberland Co., VA. He married Elizabeth, last name unknown. The Lawlesses noted of Goochland and Cumberland was undoubtedly his children: William, Elizabeth, Thomas, John, Augustine, and Jesse.
Michael Lawless, (12), son of James and Elizabeth Demsey Lawless, was born about 1715 in Essex (later Caroline) County, Virginia. Married possibly Margaret, maiden name unknown. Of the three Michaels in Essex/Caroline during the first half of the 18th century, the other two being clearly father and son, this Michael engaged in behavior similar to that of Benjamin Lawless. He was sued for assault and battery by Matthew Giles in 1736 and twice, by Jas. Boulware & Jas. Baxter, in 1741. This same Michael Lawless was undoubtedly the one found with Benjamin Lawless on the Tithable List of Lunenburg, 1748-1751. Michael joined the Lunenburg militia on 25 July 1757, shortly after Henry Lawless was killed by Indians in Augusta Co. the recruiting certificate was sent to John Cox who was later a prominent official of Pittsylvania Co. Thereafter he disappears from view; unless he was the one found later in Laurens Co., SC where on 5 June 1784, a Michael Lawless was the witness to a deed of gift by Micajah Hendrix, “planter of Pittsylvania Co. and Parish of Camden. The Laurens Co. Census of 1810 lists a widow Margaret Lawless “over 45 years” of age but could, of course, have been much older than 45. In nearby Pendleton District was a Henry Lawless, 45 years of age, and had 11 children. Asa Lawless, also listed in the same age bracket, had 6 children. Living by 1850-60 in Anderson Co., SC that had been a part of Pendleton were Asa, Azariah, David, Essey, Henry, James, Michael, and William.
Benjamin Lawless, Sr., (12), son of James and Elizabeth Demsey Lawless, was born about 1720 in Essex (later Caroline) County, Virginia. Married Mary Unknown. She was born about 1730. Benjamin Lawless first appears in the few surviving Caroline records in Dec 1745 when he demonstrated his volatile and unpredictable nature. He was at court in the case of Edw. Crowley against his purported brother Henry Lawless. The court ordered Henry to pay Benjamin for his attendance as a witness. Benjamin also had to answer for his own misbehavior; placed in the custody of the sheriff, Benjamin must pay a 1 year peace bond. Benjamin appears in the Caroline records only one other time; on 6 Oct 1747, the court ordered him to pay the balance of a debt. Thereafter, he appears to have left for the frontier. Benjamin and his purported brother Michael Lawless appeared on the List of Tithables for old Lunenburg between 1748 and 1751, undoubtedly in an area where Halifax was soon to be created. Benjamin Lawless, Sr. made his first acquisitions, in what was to be Pittsylvania, from 1755 to 1762: (1) on the ridge between the heads of the North Fork of Birches Creek and the Southern branch of Sandy Creek about l0 miles NNE of what is now Danville. (Noteworthy is the simultaneous entry in 1755 of Samuel Harris whose land abutted that of Benjamin Lawless, Sr. and who ordered the transfer of 400 acres to Wm. Lynch in l765. (2) the Fall Creek region, including Lawless Creek, to which a deed of the 1770’s referred as Ben’s fork of Fall Creek. Ben’s Fork Lawless Creek can still be found on county maps at the northeast corner of the city of Danville. (3) the long branch of Cane Creek about four miles east of Danville.
Of the 1,600 acres which Benjamin Lawless added in 1762, 800 abutted the property claimed at the same time by Henry Hardin whose daughter Sarah married Benjamin’s purported nephew Jas. Lawless III. By 1772, Benjamin Lawless, Sr. had accumulated 8,000 acres in these locations and on the South Fork of Beaver Creek which was some 2 to 3 miles west of what is now Chatham, the county seat. The identity of his wife Mary is indicated on several land transactions, although her maiden name is unknown. The prominent Theophilus Lacey became a neighbor in June 1772 when he acquired 1,600 acres abutting the property of Benjamin Lawless, Wm. Lynch, and Wm. Gwinn in the Sandy Creek area; Lacey’s overseer was Mark Hardin, son of Henry Hardin and Judith Lynch Hardin and brother of Sarah Hardin Lawless, wife of Jas. Lawless III. Thos. Burgess added 1,000 acres abutting the land of Benjamin Loyless the Burgess property originally surveyed for Jas. Walker, possibly a son of Dr. Thomas Walker noted in conjunction with Benjamin Lawless’ purported brother Henry. All the while, Benjamin Lawless continued to demonstrate the volatile temperament already observed in Caroline. He was in numerous law suits with his neighbors. He was charged several times with assault and battery in the Halifax County court before Pittsylvania was established. In 1769, he had to pay a one-year peace bond of ten pounds for “insulting the [Pittsylvania County] court;” after the charges brought by Camden Parish in 1778 against him, the Commonwealth of VA fined him for drunkenness. Later that same year the court remanded him to prison on a charge of theft; Wm. Lynch and Benjamin Lawless, Jr. had to post bonds to assure their appearance during the trial as witnesses. In 1781, Benjamin was found not guilty of stealing 3 blacks.
Then came the imprisonment ordered by the Commonwealth of VA for treason in July 1781. The charges were evidently dropped after the War for Independence, as he would soon be back in court with various civil suits. Although he had once owned considerable property, he died almost penniless in 1798; his estate consisted of one mare valued at 9 pounds that sold in time for 13 pounds 11 shillings. Benjamin’s apparent brother Jas. Lawless II, evidently had little trouble with the governing Patriot authorities until after Benjamin’s trial for treason. He and his son Jas. III, the Hardins, Lynchs, and Taliaferros took an oath of allegiance in 1777 to the American movement, as did Benjamin Lawless, Jr.; but not Benjamin, Sr. Jas. Lawless II and III may have been eventually stigmatized as a consequence of the arrest of Benjamin, Sr. for treason. As noted in the material on them, both had to post their peace bonds in 1786 and soon moved south. The imprisonment of Benjamin, Sr. for treason may have resulted from a Tory uprising in Pittsylvania during the fall of 1780, but the full story about it will probably never be told because, in subsequent years, the records were expunged of all evidence that could have tarnished permanently the reputations of some of Pittsylvania’s leading families. The uprising may have been planned to coincide with the advance of Lord Cornwallis to the Dan River and to a point no more than 10 miles from the Lawless property. Several historians have commented about the great turmoil of 1780/81 a regional civil war between the Loyalists and Patriots that spread from Pittsylvania and Halifax Counties northward to Bedford, Charlotte, Prince Edward, and Amherst Counties. Even members of the same family were frequently on opposite sides.
Two of the most noteworthy encounters between the Patriots and Loyalists occurred on Kettle Creek in Wilkes Co. and on Brier Creek in an area that became a part of Warren Co in 1793. Was there a rumor mill in the “upcountry” from Virginia to northern Georgia a region so integrated socially and culturally that Professor Carl Bridenbaugh treats it more or less as a separate, fourteenth colony? If so the stigma may explain the “Loyalless”, written by the recorder in bequest in 1790 of Jas. Loyalles, Jr., who could not have known of the mistakes because he could not read or write or even sign his own name. Incidently, Reuben Lawless could sign his name as such in administering the estate of his father but appears on the 1794 tax list of Wilkes Co as “Reuben Loyalless”. In any case, perhaps the step father, John Burkhalter, from a notable German family of Patriots in GA, decided on the name Loyless for James, Henry, and Lucy to save them embarrassment. The real explanation may be simpler. A correspondent who descends from Augustine Lawless, writes that several generation back a KY ancestor going into politics decided Lawlace might look better to the public than Lawless. However a linguistics Professor has suggested that the Lawlesses who where newcomers to GA may still have had such heavy Irish accents that their pronunciation of their names would then have come across to any county recorder or official much like the English sounding “Loyalless”. Benjamin died in Pittsylvania County, Virginia in 1798. They had eight children: Henry, Richard, William, Benjamin Jr., Jesse, John, Thomas Byrd, and Susanna.
James Lawless II, (12), son of James and Elizabeth Demsey Lawless, was born about 1725 in Essex (later Caroline) County, Virginia. The first reference to him in the Caroline County, Virginia records is in a document 23 Nov. 1741 that suggests he was then a teenager John Jones produced a certificate from Geo. Hoomes for taking up a runaway servant named James Lawless belonging to Jas. Johnson of Essex Co. “On 14 June 1746, James Lawless acknowledged his “deeds and lease and release” to Henry Lawless, probably his brother. On 14 Feb. 1747, Wm. Jeter sued James Lawless successfully on a debt.
He became a part of the movement by the families Gatewood, Ware, Taliaferro, Upshaw, Rowsey, and Lomax to Amherst Co., Va. where he lived until ca. 1769/70 when he accompanied Dr. John Taliaferro and wife Mary Hardin to Pittsylvania Co. Va. where his presumed brother Benjamin Lawless had been living adjacent Mary Hardin Taliaferro’s father Henry Hardin. The only Lawless on the Tithable List of 1767 for Pittsylvania Co. was Benjamin Lawless. The first record of Jas. Lawless in Pittsylvania Co. was one of Aug. 1770 when he is shown to have been in possession of some of the Fall and Lawless Creek property previously in possession of his brother Benjamin. He acquired 400 additional acres on 29 Dec. 1770 adjacent Benjamin’s long-time neighbor Chas. Clay. On 2 Nov. 1774, he added 138 acres on head branches of Fall Creek near White Oak Mountain and adjacent Chas. Clay and near property of Henry Hardin and Benjamin Lawless.
VA Heads of Families in 1782 show him as the head of a household of 6. An indication as to the general time frame for his birth comes from a court record of 1782 that shows him exempt from taxes. In 1785, Jas. Lawless II successfully sued Benjamin Lawless, Jr. as the executor of the estate of Eliz. Buckner for 40 pds. 8 shillings; but Benjamin, Jr. had to pay Benjamin Lawless, Sr. and Wm. Cottrell 250 lbs. of tobacco each for attending trial as witnesses for ten days. Jas. Lawless II married Mary Taliaferro, daughter of Dr. John Taliaferro’s first cousin Lawrence Taliaferro 1683-1726.
He and wife Mary evidently followed Dr. John Taliaferro to NC, as the state census of 1787 shows them in a household of two in the district of the former Pittsylvania Capt. Thos. Farguson. They may have accompanied their sons Reuben and James III and possibly another son John in 1790 to a part of Wilkes County (later Warren), Georgia. John Lawless settled in Elbert Co. The last record of James Lawless II was in Warren County, Georgia. 1 March 1796, Reuben Lawless, his son and will executor, signed a statement acknowledging that a hearing in Warrenton had produced evidence from witnesses to whom Reuben had sold 300 acres of the Fall Creek property in Pittsylvania Co., Va. to a John Weldon; Reuben signed and delivered the deed in person in Warren Co., Ga. The affidavits from the hearing satisfied the court in Pittsylvania that a valid contract had been consummated. He died in 1796 in Warren Co., GA. They had five children: Richard, Reuben, James III, John, and Michael.

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