No one knows with certainty how David O’Killia/O’Kelley (the surname Kelley was spelled fourteen different ways in the Yarmouth Vital Records) ended up in Plymouth Colony in the 1600s. Most of the colonists were of English descent, so where’d the Irish guy come from? It was so unusual for someone to be from Ireland that he was sometimes called “David the Irishman” in records.
It is possible he was a prisoner of war by the English and sold in America as an indentured servant. England's subjugation of Ireland, which occurred 1641-1654, caused hardships among the Irish and many prisoners of war, orphans and the destitute were seized by English authorities and sold as indentured servants. One 1661 entry in Plymouth Colony Records mentions William Hifreny, an Irishman and servant who had been "stolen from his own country."
David was first an indentured servant for John Darby, then Edward Sturgis, both of Yarmouth. Servants were not always domestic help—they could be manual laborers, tradesmen, mariners, mechanics, husbandmen, and teachers. They were indentured for a period of time, usually 3 to 10 years, in exchange for passage to America. His service expired about 1657 when he took the freemen's oath at Yarmouth, so he was probably born 1630-1636.
On 4 Oct 1655 David is recorded in Plymouth Colony Records as David Ogillior. On this date Jane Powell of Sandwich is charged with fornication: "And att this Court, Jane Powell, servant to William Swift, of Sandwidge, appeered, haveing been psented for fornication, whoe, being examined, saith that it was committed with one David Ogillior, an Irish man, servant to Edward Sturgis; shee saith shee was alured therunto by him goeing for water one evening, hoping to have married him, beeing shee was in a sadd and miserable condition by hard service, wanting clothes and living discontentedly; and expressing great sorrow for her evell, shee was cleared for the psent, and ordered to goe home againe."
Burt Derick wrote in Gaelic Love on Cape Cod: David, the Irishman, and Jane, the Welsh Maid, Dennis Historical Society Newsletter, Feb/March 2008, that David and Jane’s story is one of loneliness and love. The Separatists realized they needed to bring in willing workers, which was easy given the strife in Great Britain from wars, ravages of plague and religious persecution. Nearly all were young and unmarried, at the bottom of the social class.
David and Jane were poor bondservants, in their teens, forced to endure great hardship. Jane was likely originally from Wales. It is possible, but unlikely, that she is related to the Powells of Boston as William Swift Sr. lived there. William Swift Jr. resided on the present Standish Road in North Sagamore, now the town of Bourne, and owned Jane's indenture. She would have had a busy time caring for Swift's 10 children. The distance between Swift and Sturgis' homes is 24 miles, quite a distance in those days. Perhaps they met on the same ship from England to America.
David and Jane were poor, lonely, scared, moving to an uncertain future and they were Gaelic, sharing a common language others on the ship may not have had. They would have been immediately separated and endured a hard life, as Jane's plea in court shows. Many of the colonists were religious fanatics, ruling with an iron hand, punishing people for minor infractions. Somehow, in a time when roads were less than cartways and transportation was slow, David found Jane. Perhaps he had an errand to do for his master, attending the only gristmill in the area to get the corn ground to flour. It is unlikely it was a chance encounter--not a single encounter in the woods of Sagamore, but one of many. There was certainly a background relationship between these people that resulted in the encounter for which they were charged. The fornication charge likely means she was pregnant, rather than caught in the act.
Despite Jane's guilt, the magistrates could not bring themselves to levy the typical punishment of public whipping and they sent her home. They also didn't charge David with seducing the girl. They leave the two to work out the problem. It's also remarkable the Clerk took time to record so many details of Jane's predicament
After securing freedom for both of them, David did the honorable thing and married Jane and they moved to a 100 acre farm that was eventually named Kelley's Point, at the head of Bass River on the banks of what is today called Kelley’s Bay. The area is now called Mayfair in current day South Dennis, Massachusetts.