The Man Who Loved to Sue

By Alicia Bertrand, M.A.

Most of us have heard stories of frivolous lawsuits: the man who sued Kellogg’s because Froot Loops aren’t made with fruit,[1] the woman who sued a grocery store after tripping over her own child in an aisle,[2] or the man who sued his parents for creating him,[3] among others.[4] In 2020, the U.S. Courts saw the number of civil lawsuits increase 16%.[5] Frivolous lawsuits are not new. Over 300 years ago, Robert Cross was part of numerous lawsuits, both in suing people in his community, and being sued by them as well, numerous times throughout his life in the 17th century. One of Crosses’ most well-documented lawsuits was against a man named William Durkee, who was sued for fornication and impregnating Martha Cross, Robert’s daughter, in 1664. Were his lawsuits frivolous, or were they necessary to uphold his reputation and obtain monetary debts? Centuries later, we can only judge him through our modern lens.

Early Life

Robert Cross was born on June 26, 1612 in Somerset, England to Thomas Cross and Rachel Dising.[6] He immigrated to the United States in 1634 on the John & Mary. The year after, he married Anna Jordan in Massachusetts. Before the couple could have children, Cross served as a soldier in the Pequot War.[7]

Legal Troubles

In 1642, Cross encountered his first lawsuit. He was sued by John Fuller. No reason was given in the court record.[8]

In 1648, Essex County records note that Cross was under Major Daniel Denison’s salary. He was most likely the Captain of the Ipswich military group that Cross was part of in the Pequot War, and therefore, it would make sense that he continued to work with Major Denison. However, this relationship would falter. In 1663, Cross was fined and forced to acknowledge his “scandalous words” against Major Denison. Cross alleged that he could “get no justice so long as the Major sat on the bench.”[9] Major Denison was a consistent member of the Ipswich court.

On March 31, 1649, Cross took Joseph Fowler to court for “wicked sinful speeches concerning Robert Crosse”.[10] Two of the witnesses were Crosses’ daughter-in-law and granddaughter. In the same court proceeding, Fowler was sentenced to “sit in stocks for an hour and a half or pay a fine for saying there were seven or eight liars in the church.”[11]

On January 25, 1651, Cross took Cornelius Waldo to court, but William Cogswell (possibly Waldo’s brother-in-law),[12] testified that Cross said he would pay Waldo 50 shillings (see chart in footnotes)[13], but only paid him 25s. Cogswell testified that Waldo responded that he would rather have that than nothing.

In September 1666, Cross had taken Thomas Varney to court. The reason was not listed in the court record. He must have lost his case, as he had to pay Varney “costs.”[14]

In the same month, he and his wife Anna testified in a case against Thomas Wells for their neighbour and friend Richard Brandbrook, who Wells called “a common liar.”[15] Two months later, Cross sued Wells for slander. Wells called Cross “a cheating knave and that he should have as good trading with the Devil as with him, and better too.”[16] Wells was forced to make a public announcement in court to “clear the good name of said Cross.”[17]

Just two months later, in November 1666, Cross was taken to court by Thomas White, on behalf of Martha Halfield. Halfield’s daughter, Rachel, had married Crosses’ servant, Lawrence Clinton, and gave him £21 to pay for the remainder of his indentured servitude. However, Clinton testified that Cross was “unwilling to take the money,” as “a servant was of more consequence than money.”[18] Much was made about their 13-year age gap, and whether the 23/24-year-old Clinton had taken advantage of the 36-year-old Halfield’s money, as Halfield was rumoured to have gotten the money from her mother by lying. Thomas White, Rachel’s brother-in-law, believed that Rachel was lying about the ordeal and took Cross to court to retrieve the money. Rachel Halfield testified that Cross, and one of his sons, insisted she marry Clinton. She claimed that Cross wanted her as a maid and would pay her “better than her father ever could.” She also stated in court that Cross and his son told her of Clinton’s rich uncles and mother, which swayed her decision.[19] Martha Halfield won that case. However, Cross appealed, and won.

In June 1677, Cross took Hugh March to court for an unpaid debt and won.[20] March owed Cross 6000 pine boards.

The Servitude and Punishments of Nicholas Vanden

In September 1666, Cross took Nicholas Vanden[21] to court for stolen goods. Vanden was Crosses’ indentured servant. He had allegedly stolen numerous goods from Cross and neighbours, and ran away. Bernard W. Doyle cited that Vanden had broken open one of Crosses’ chests and stolen a comb worth 12d (see chart in Footnote 13). However, there is no citation from which he obtained this information.[22] After being detained, Vanden was sentenced to repay double the amount of the goods taken, which amounted to £21, 3s, 2d by rendering service. He was also to be whipped for running away, breaking out of prison, and stealing.[23]

In March 1668, Vanden ran away a second time, was caught, and taken to court. After this instance he was ordered to be “severely whipped” and to pay £15 to Cross, £5 to the town for the outcry caused in the community,[24] and Cross was given the choice of putting an iron collar around Vanden’s neck as punishment.[25] Lina Cherry noted in her genealogical book in 1945 that he “chose” not to put the iron collar on Vanden’s neck, however, there is no evidence in the court records of this decision. Also, throughout her account she confused Robert Cross Sr. and his son Robert Cross Jr.[26] Both men led litigious lives in Ipswich, and the court records do not always add “Jr.” to the reference of the individual, however, if the case is read fully, the age of the individual, or the name of the wife as a witness, clearly indicates which Cross the court refers. Therefore, the account and the assumption that he did not put the iron collar on Vanden, cannot be trusted with incorrect citations, references, and other questionable items.

In March 1670, Vanden was noted by the court as having run away numerous times. Cross was owed £40 for this instance, due to £9 being stolen, but also monetary fines for the trouble of finding him. He was ordered to be “branded on the forehead with the letter R and to be severely whipped.”[27] If he was indeed branded, the pain must have been immense.

The court records did not mention Vanden again after this. Did he die of an infection from the branding? Did Cross take up the courts’ allowance to send Vanden to any English country for 10 years?[28] Without deeper research into Ipswich records, we may never know.

The William Durkee Conundrum[29]

Robert Cross was 30-years-old when his third daughter, Martha, was born on March 15, 1643. When Martha was 21-years-old she began work for Thomas Bishop, most likely as a maid. She met 30-year-old Irish immigrant, William Durkee, Bishop’s indentured servant, and the two began a sexual relationship.

In October 1664, Durkee was charged with fornication. The town found out Martha was pregnant. The Bishops’ advocated for the couple in court, and in numerous instances, stated that they would help the two with fines and other matters.

For the fornication charge, Durkee was sentenced to be whipped, not over twenty times, and to give the town of Ipswich £20 in case the child was taken into the town’s care, or he could go to prison.[30]

The conversations must have been difficult between the families. Martha had, numerous times, attempted to communicate with her father, and Durkee upon learning she was pregnant. At first, Durkee seemed to panic and was confrontational with Martha about her pregnancy and the paternity of the child. However, after discussions with friends, and Martha’s pleadings, he realized that he must be the father and had to be responsible.

Martha confided in her bosses’ wife, Margaret Bishop, her married sister, Elizabeth Nelson, and another female neighbour, Grace Searle, for advice. At first, these witnesses testified that Durkee seemed to not want anything to do with Martha.[31] In testimonies from numerous Ipswich citizens, Martha was said to be afraid that she had “been cast out of her father’s favor” and would not tell her father that she was pregnant without her sister Elizabeth by her side. Martha was noted to be “horrified and distressed in mind.”[32]

Durkee took Robert Cross to court when it was alleged that he refused to give his blessing for their marriage. The Bishop’s advice led Cross to give his consent to the couple to marry in a letter stating: “…we shall no ways hinder it: [–] hearts are sore oppressed. We are as full of sorrow as the [–].”[33] The court ruled in Durkee’s favour, and Cross had to either give his consent to the marriage, or pay £5 in damages.

John Bishop,[34] testified that Durkee said if he could choose one or the other, he would rather keep the baby than Martha, but since they were set to be married the day after, he would have to stick with both.

Martha and Durkee were married on December 20, 1664 in Ipswich.[35] Their son, John, was born two weeks later.[36] In March 1665, the town decided it was enough time after Martha had given birth for her to be charged with fornication and sentenced to be whipped or pay the treasurer £3.[37]

Although Durkee had cold feet at one point and only wanted the baby instead of Martha, the couple stayed married and had 7 children.[38] The family would live in poverty, due to Durkee’s refusal to renounce Catholicism, nor attend the local church. Therefore, he could not own land and was charged by the court for not attending church. The fines were paid by Thomas Bishop. He was also sentenced to receive 25 lashes.[39]

Robert Cross left his daughter and her new husband alone, and did not take them to court for anything further.

Image by Gordon Johnson from Pixabay

Only Death Could Keep Him from the Courts

On November 25, 1682, 70-year-old Cross was in the courtroom in regards to a 30-year-long controversial contention of a 30-acre parcel of land in Chebacco.

In April 1695, 83-year-old Cross appealed a verdict in favour of John Burnham Jr. by the Salem Inferior Court in which the court granted him the 30-acres in Ipswich that Cross claimed as his land. He testified to the decades of ownership, whom sold to whom, and the Superior Court of Judicature ruled in his favour.[40]

After this case, there is no more courtroom drama for Cross. He possibly died sometime after the appeal in 1695. However, Chebacco historians could one day find evidence of his actual death date among the records. He called himself “the ancientest man and first proprietor that ever lived on the South side of the Chebacco River.”[41]

Robert Cross lived a litigious life. He spent a lot of time in courtrooms until his death. Even after, his name would be mentioned in land dispute claims by his sons, Robert Cross Jr. and Captain Stephen Cross. Whether it be litigation against his indentured servants, neighbours, or his daughters’ future husband, Cross had to protect his reputation in 17th century society. Although he was not the only townsperson to litigate disputes in Ipswich, the case against Durkee sets him apart from the others. We can gain insight into the lives of colonial New England citizens through what disputes were litigated. Property, finances, and social reputation were very important. Maybe three and a half centuries later, we’re not so different after all.


[1] Sajid Farooq, “Man Sues Froot Loops for Not Being Frooty at All,” NBC Bay Area, September 29, 2009, online at:

[2] Suffolk Gazette, “Mum sues store after tripping over HER OWN daughter,” online at:

[3] Jeremiah Rodriguez, “Indian man suing parents for giving birth to him,” CTV News, February 8, 2019, online at:

[4] John Harrington and Hristina Byrnes, “A man sues himself? A docket of 25 of the weirdest, silliest and frivolous lawsuits,” USA Today, February 3, 2022, online at:

[5] United States Courts, “Federal Judicial Caseload Statistics 2020,” online at:

[6] Anderson, Robert Charles. The Great Migration Begins: Immigrants to New England, 1620-1633, Volumes 1-3; The Great Migration: Immigrants to New England, 1634-1635, Volumes 1-6. Boston: New England Historical and Genealogical Society, 1996-2011, pg. 40.

[7] I am disgusted to know that my ancestor took part in the murder of any Pequot indigenous peoples. If it is possible to apologize on his behalf, I would gladly do so. The Pequot are described by the Britannica as “any member of a group of Algonquian-speaking North American Indians who lived in the Thames valley in what is now Connecticut, U.S.”

[8] George Francis Dow, Editor, Records and Files of the Quarterly Courts of Essex County, Volume I, [Transcribed and Abstracted from the Original Court Manuscript by Harriet S. Tapley], (Essex: Essex Institute, 1911), pg. 41. <;

[9] George Francis Dow, Editor, Records and Files of the Quarterly Courts of Essex County, Volume III, [Transcribed and Abstracted from the Original Court Manuscript by Harriet S. Tapley], (Essex: Essex Institute, 1913), pg. 65.

[10] Vol I, pg. 168.

[11] Ibid.


[13] British Monetary Meanings Prior to Decimalization Chart:

£ = pound

s = shilling

d = pence (Pennies were abbreviated to ‘d’, representing the Latin word for this coin of ‘denarius’.

[14] Vol III, pg. 350.

[15] Vol IV, pg. 50.

[16] Vol IV, pg. 66.

[17] Ibid.

[18] Vol III, pg. 371-372.

[19] Clinton and Halfield later divorced in 1681. She was tried for witchcraft, imprisoned, and escaped. She lived out the rest of her life in a hut on her mother’s land in Ipswich. Henry Edwards Scott (Editor), The New England Historical and Genealogical Register, Volume 69, (Boston: New England Historical Society, 1915), pg. 50-51.

[20] Vol VI, pg. 285-286, 394.

[21] Also spelled Vauden in primary sources.

[22] Bernard W. Doyle, Comb Making in America, (Boston: Perry Walton, 1923), pg. 14.

[23] Vol III, pg. 351.

[24] The court stated he caused a hue and cry, which was the process of bystanders being summoned to assist in the pursuit of a criminal. Vol IV, pg. 10.

[25] Ibid.

[26] Lina Vandegrift Denison Cherry, Ancestry of my three children; Lewis Williamson Cherry, George Denison Cherry, Carolyn Vandegrift (Cherry) McDonnell. Extended, proven, comp. and ed. by John Cox, Jr., (Little Rock: John Cox Jr., 1945), pg. 186.

[27] Vol IV, pg. 234.

[28] Vol IV, pg. 10.

[29] His name is spelled numerous ways in primary sources. See also: Dirkee, Dirkey, Dirky, Durgee, Durgi, or Durgy.

[30] Vol III, pg. 198.

[31] Vol III, pg. 189-190.

[32] Ibid.

[33] English spelled in modern spelling. Original spelling can be read in the original source. Ibid.

[34] Likely Thomas and Margaret Bishop’s son.

[35] Town and City Clerks of Massachusetts, Massachusetts Vital and Town Records, (Provo, UT: Holbrook Research Institute (Jay and Delene Holbrook)), pg. 45.

[36] John was born on January 3, 1665.

[37] Vol III, pg. 242.

[38] One of their children, Mercy, is my 7th great-grandmother. William and Martha are my 8th great grandparents, and Robert is my 9th great-grandfather.

[39] So says The Society of Genealogy of Durkee, online at:

[40] Robert Charles Anderson, The Great Migration Begins: Immigrants to New England, 1620-1633, Volumes 1-3; The Great Migration: Immigrants to New England, 1634-1635, Volumes 1-6. (Boston: New England Historical and Genealogical Society, 1996-2011), pg. 242.

[41] Joan Sheridan Guilford McGuire, The Ancestry of Dr. J.P. Guilford: Seventeenth-century New England colonials, (New England: Sheridan Psychological Services, 1990), pg. 187.


Published by AncestryByAlicia

After obtaining my Master of Arts degree in History, and working on my genealogy for over 13 years, I decided to write about interesting historical matters from not only my family, but other interesting tidbits as well. I also research and present free walking tours in my city, including "Haunted Oshawa" and "Murder and Mayhem in Oshawa." I am currently writing two books. One is a historical account of small-town murders in Ontario. The other is a historical novel about the Royal African Company's James Fort on the Gambia River, 1715-1740.

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