Henry and Lydia Bennett
When Lyonell signed the indenture agreement with Henry and Lydia Bennett in 1779, both the Bennetts and Okemesw8 would have recognized that they were defying their powerful neighbors Daniel and Elizabeth Epps. Later Daniel Epps said in court that Okemesw8 accepted that Lyonell belonged to him. He testified that she ”allwayes sed your Boy Lyonell” and ”did always acknowledge him to be so to be whoesoever was present there.” [1] It appears that Okemesw8 did not challenge Epps’ claim on Lyonell directly. She continued to visit her older grandson Daniel at Castle Hill and knew that Epps could attempt to remove Lyonell at any time.
Okemesw8 appears to have develped a twofold strategy.
First, she delayed the inevitable. Daniel and Elizabeth Epps abdicated their Puritan responsibility to bring Lyonell under their family government most likely because they assumed he would work for them later.
Second, she cultivated allies who had the motivation and resources to defy their powerful Puritan neighbors. Henry and Lyida Bennett had ample reasons to defy Daniel and Elizabeth Epps.

Although the exact boundaries between the colonists were poorly defined, the location of cermionial shell cirlces on Castle Neck can be located more precisely. In this 1931 map, William Moorehead documents sites where shell circles were discovered on Castle Neck.
In 1665, shares of the common land on Castle Neck and Plum Island were distributed to individual settlers. [2] While some of these shares were harvested for marsh hay or planted with crops, most shares appear to have been viewed as equity in this land. Henry Bennett, who already controlled 200 acres where Russel’s Orchard is today, acquired 100 upland acres on Wigwam Hill. At the same time, Daniel Epps acquired many lowland acres between his farm at Castle Hill and Bennett’s land at Wigwam Hill. The boundary between Bennett and Epps was poorly defined.
Henry Bennett’s son Jacob had a 100-acre farm on Hog (Choate) Island just across Chebacco Creek from Wigwam Hill. In March 1678, Jacob cut down 20 pine trees on what he believed was his father’s land at Wigwam Hill. Epps sued Bennett claiming that the trees were on his land. Many witnesses testified about the boundary. A careful reading of court testimony shows that the boundary could not be identified adequately. Despite this ambiguity, Epps was given the benefit of the doubt. He may have won the case due to his elevated social status, not from the facts on the ground.

In Downriver – A Memoir of Choate Island, Agnes Choate Wonson remembers that even in the early 1900s the Pawtucket continued to harvest the abundant resources of Chebacco Estuary, picking sweet grass on Dilly Island nearby.
For countless generations the Pawtucket depended on Castle Neck and Chebacco Bay as an abundant and accessible source of natural resources This continued into the 1900s. There is no reason to believe that these resources failed to provide for Okemesw8 and Lyonell.
Henry Bennett has been described as “a shrewd, sagacious, energetic man, though his education seems to have been quite limited”. [3]
Bennett appears to have made at least part of his fortune harvesting the abundant pine on Castle Neck. A cord of pine sold for twenty pence, but by sawing the pine into boards one inch thick, a settler could charge thirty pence.[4] Much of Bennett’s profit appears to have come from the additional value of delivering these boards to ports along the coast including George’s Bank. This helps explain why Bennett would claim the pines growing at Wigwam Hill, while Epps would claim the marshland to harvest hay for his livestock.
Okemesw8 gambled on Bennett honoring his agreement to release Lyonell at 21. Bennett’s indenture of Lyonell was not purley an attempt to defy his Puritan neighbor and assist Okemesw8. Like Epps, Bennett acted in his own self-interest. Like Epps, Bennett enslaved a native child.
Okemesw8 could hope that in 1690 both Daniel, age 24, and Lyonel, age 21, would be released at the term of their indenture. There are no records confirming that her gamble succeeded. Colonial records demonstrate that indentures were often extended beyond their initial term and could be extended for a lifetime.

Servant or Slave?
Daniel Gookin was known as the “Guardian of the Indians”. He also was an enslaver. When he came north to Massachusetts from Virginia, he brought with him an enslaved child named Silvanus. Although Gookin promised to free Silvanus, he never did. Instead he sold Silvanus to another settler. Gookin was responsible for removing the children of Praying Indians from their families and giving them to prominent Puritan families. Were these children servants or slaves?
“Indians could find themselves in any of a number of forms of involuntary servitude and slavery. Slavery and servitude were poorly defined terms in English America for much of the seventeenth century. Contracts, writs, bills of sale, and even legislation often used the two conditions interchangeably. Ultimately, chattel slavery and freedom were at opposite ends of a broad spectrum, and many Indians occupied points along that spectrum in varying degrees of unfreedom. Slavery might be a temporary status, while servitude might be lifelong.”
“Indians seldom had written indentures or contracts with their English masters—a factor that distinguished them from their English counterparts. This sometimes made the ad hoc enslavement of Indians a matter of a decision on the part of an individual English colonist to define a particular Indian as a slave for the economic advantage this change brought.”
Encouraging Lyonel to indenture himself to Bennett must have been heartbreaking for Okemesw8. Looking back almost 350 years later, it is difficult to imagine without historical context how a native grandmother would allow her 10-year-old grandson to bind himself to a settler who was colonizing her homeland.
Neither of Okemesw8’s grandsons would have been free from assimilation into the culture of the settlers who were colonizing her homeland, but she may have hoped that the depth of assimilation would have been less with Bennett than with Epps.
[2] Thomas Franklin Waters and others, Ipswich in the Massachusetts Bay Colony .., 2 vols (Ipswich, Mass., The Ipswich historical society, 1905), ii, pp. 89-92.
[1] Massachusetts County Court (Essex County), Records and Files of the Quarterly Courts of Essex County, Massachusetts Vol 9, vol. 9 (Essex Institute, 1975) p. 252.
[3] New England Historic Genealogical Society Staff, The New England Historical and Genealogical Register,: Volume 29 1875 (Heritage Books, 1995), p. 168.
[4] Thomas Franklin Waters, Ipswich in the Massachusetts Bay Colony …, vol. 2, 2 vols. (Ipswich historical society, 1917) p. 735.
