In 1665 Cross, who owned a fairly sizable estate, had employed newcomer Lawrence Clinton as an indentured servant (someone contracted to an employer for a specified length of time in exchange for free passage from Europe to the colonies). Almost immediately Clinton became involved with Rachel Haffield, who was single and wanted to be married. At this time, an indentured servant could be released from a contract only by paying the employer the balance of money due on the contract. Thirty-six year old Rachel and twenty-two year old Lawrence could not marry immediately because of this one stipulation, so Cross agreed to free Lawrence for the price of twenty-one pounds (an amount of British money). Rachel was still informally in charge of her mother's estate and cash, so she easily obtained the funds to free Clinton from his obligation. A year later her brother-in-law Thomas
White took over the Haffield estate, and he decided to hold Cross accountable for the money because he claimed it had been illegally obtained. White charged Rachel with stealing the money from her mentally ill mother and pointed an accusing finger at Cross, whom he felt had taken advantage of Rachel's desire to wed.
Although it was common knowledge in Ipswich that Rachel had her mother's permission to handle the family money, there was never any formal written agreement. When the court granted power to White it robbed Rachel of any legal standing and made her look like a criminal for using the funds to free her future husband. In the court trial over the twenty-one pounds the jury decided in favor of White. This decision was reversed just a few months later, so Cross set up an elaborate scheme in hopes of reaping further profit from the case. He urged his former servant to marry Rachel and gain full access to her family's estate. He then told Rachel lies about Clinton's wealth in hopes of speeding up the wedding. According to Entertaining Satan: Witchcraft and the Culture of Early New England court records indicate Rachel felt used and cheated: Cross "told me a thousand lies more to delude me, so as to be married to him [Clinton] and to cause me to put money into his hands. Further, this deponent sayeth that in case the money now in controversy were taken from him again, then he would sell me and my husband Clinton for servants."
This time the jury found in favor of Cross, who was given back his twenty-one pounds. White let the case drop and focused his attention on selling off parts of Rachel's land, including the cottage where she had lived with her mother. He forced Martha to move in with him and his wife, leaving Rachel with nothing. In March 1668, almost immediately after the move, Martha died and the controversy over her holdings reached an even more intense level. The family farm was valued at about 300 pounds, and her own personal property was estimated to be worth about 50 pounds. White tried to seize everything and then attempted to collect a guardianship fee from the family, at the rate of 22 pounds per year, for taking care of Martha. He also added court costs involved in his case against Cross as well as expenses for Martha's funeral to his demands.
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