Anne Orthwood was born August 13, 1639 near Bristol, England. By age 22, she had decided to go to the new colony of Virginia. The least expensive way was by becoming an indentured servant. She sold her servitude to Colonel William Kendall. The colonel had begun his days in Virginia as an indentured servant and had worked his way into the upper echelons of Virginia society, where he had become one of the most powerful politicians. Anne moved to Newport House Plantation and worked in the house as a servant.

Colonel Kendall had a young nephew, John, who had moved to Virginia from Norfolk, England. In his early 20s, John helped his uncle run the plantation. And this is where Anne met John. They soon began an affair.

Like many men who have had difficulty climbing the social ladder, Colonel Kendall, when he found out about the two, was most fearful of scandal. Not just a scandal of sex, but even one of different classes falling in love and messing with the social order. So, the loving uncle sold his contractual rights of indenture to Jacob Bishop, a man very high in the social order, with his own large plantation. Being as there was no courthouse in the county at the time, the council met at Webb’s Inn to approve the purchase. And there, Anne and John met again in November of 1663. They managed to consummate their love by conceiving twins that very weekend. John immediately stopped the relationship, never acknowledging anything.

Anne hid her pregnancy as long as possible, possibly due to shame or the expected punishment once someone found out the truth. By late spring, she could no longer hide it. Bishop sold her indenture to Colonel Williams Waters, justice of the peace and well-to-do gentleman, avowing that the young lady was well enough to work, and a virgin. Waters soon found out differently, complained and had her arrested. Anne was questioned but refused to indicate who the father was.

Anne was in prison for almost two months until she went into early labor. She was denied a midwife until she released the father’s name. Eventually, Anne gave John Kendall’s name. But she died of complications, along with one of the two twin boys. The baby Jasper survived.

In the meantime, Colonel Waters was angry at being shysted by Mr. Bishop. Waters had been sold damaged goods. The servant could not work. Waters wanted a refund and did not wish to care for the servant girl. English law read that wherever the servant girl lived at the time of becoming pregnant, that owner had to care for her. Waters was not obligated. Bishop did not want the responsibility. Bishop was called out of town at the beginning of the lawsuit and did not return until Anne died. Waters was awarded his down payment and court payments.

Several weeks after Anne’s death, a civil liability charge was brought against John Kendall. The court ruled that John owed maintenance for baby Jasper. This was probably decided to save the public the tax money needed to maintain the child. But then they ruled that John was not the father, to save his life from being socially ruined.

However, this last statement required the formality of a trial. The conclusion of the court was that since it was only seven months from the date of Anne and John’s meeting, the child could not be John’s because everyone knows it takes nine months. Anne’s credibility in naming John was doubtful since she was in terrible pain while being interrogated.

Twenty-one years later, another trial was held, dependent on the same scenario. Jasper was now over 21 and had been bound over as a servant from infancy. John Kendall had paid the child’s way but had not taken his own son in. Jasper was, now, an indentured servant to John Warren. Jasper requested to be released and was denied. The English law that Warren cited claimed an indentured servant had to remain until age 24. So, Jasper hired a lawyer and sued Warren, based on a colonial law that read that illegitimate children were indentured only to age 21. Jasper won.

Despite the hardship that Anne went through, she will be remembered for the attitudes of councils.  Which laws the court would choose, rule by, or ignore was based on how the people in the community felt about the case being prosecuted. With criminal conduct cases, the court acted upon moral justification rather than law. In paternity cases, they acted upon the community’s best financial interests, finding a responsible party to take the burden off themselves.