Uncovering William Simson's Story: How AI and Digital Records Solved a 350-Year-Old Family Mystery

For years, family researchers knew the basic outline of our ancestor William Simson's story. In 1676, the Duke of York granted him 400 acres in Kent County, Delaware, called "Simpson's Choice." But somewhere along the way, he lost his land. We knew this because later records showed John Richardson selling off pieces of the Tract. The mystery that had puzzled us was simple yet frustrating: when and how did William lose his land?

I finally found the answer thanks to FamilySearch's revolutionary new AI-powered full-text search capability. But the truth turned out to be more complex and fascinating than I had imagined.

The Breakthrough Discovery

The breakthrough came when FamilySearch's AI transcription tools helped me locate a "Brief of Title" document for Simpson's Choice. This legal summary laid out the whole chain of ownership:

Brief of Title
William Simpson took up the whole Tract called Simpsons Choice. The patent is to Simpson, & is Recorded in the Rolls Office at Dover, in Book B, folio 27.
Assignment from Jno Brinckloe of the whole Patent to John Edmondson, Book B, folio 37.
Assignment from Jno Edmondson to Jno Richardson sen (for the same), Book B, folio 38.
[The document continues with further subdivisions...]

This was the smoking gun I'd been looking for! But it also raised a new mystery: if the patent was granted to William Simpson, why did John Brinckloe assign it to John Edmondson? How did Brinckloe get control of William's land?

When AI Became My Research Partner

Frustrated by inaccurate indexing and hard-to-locate documents, I turned to Google's Gemini AI for help. I explained the puzzle: William got the patent, but John Brinckloe somehow transferred it. Gemini's response was illuminating. It suggested this looked like a sophisticated land speculation arrangement common in the colonial period.

After some discussion, Gemini explained that wealthy, well-connected men like Justice John Brinckloe, a local Kent County official, frequently exploited recently arrived immigrants as fronts for land patents. While the immigrant would appear as the named patentee, the true financier retained actual control of the property. This practice was widespread in Maryland, where former indentured servants were entitled to land grants but large landowners sought to expand their tobacco-growing estates. The scheme was also common in Delaware, despite opposition from Edmund Andros, the Duke of York's principal, who was notably hostile to the land speculation practiced by figures like John Edmondson and John Richardson. Edmondson alone bought and sold over 68,000 acres across Delaware and Maryland.

This made perfect sense given what we know about William Simson; he had likely arrived as an indentured servant in the late 1660s and would have been ambitious but essentially penniless by 1676.

Finding the Missing Pieces

Reviewing the actual patent document from March 1676. The crucial detail was at the bottom: a notation reading "True Copy, Examined by me, John Brinckloe." This proved that Justice Brinckloe had been officially involved from the very beginning. He wasn't just a later player in the story; he was the orchestrator.

Gemini then helped me find the September 1678 assignment document, which was in plain sight all-along, right after the patent document. The language was unambiguous: "I John Brinckloe doe make over all my right tittle & intrest of this within mentioned Pattent... unto John Edmonson..."

Brinckloe was the one with legal authority to transfer the property because he had been the agent and likely financier all along.

The Real Story Emerges

What emerged was not a story of William Simson losing his land but rather the tale of a sophisticated business arrangement that gave him his start in America. Here's what actually happened:

The Setup (c. 1668-1675): William Simson possibly arrived in Maryland as an indentured servant around 1668. After completing his term of service, he would have been a "freeman" but without capital to purchase land. He then journeyed east to the then-frontier of Delaware, making him the perfect candidate for what followed.

​The Patent (March 1676): The 400-acre tract "Simpson's Choice" was patented in William's name, with Justice John Brinckloe handling the official paperwork and likely paying the fees. Brinckloe served as agent, financier, and clerk for the entire deal.

The First Transfer (September 1678): After William had occupied the land for two and a half years, probably receiving both lodging and a cash payment, Brinckloe transferred the patent to John Edmondson, the wealthy Quaker merchant from Maryland who was the intended investor from the beginning.

The Speculator's Flip (March 1679/80): In a move that reveals the true nature of this venture, Edmondson held the property for only 18 months before selling it to John Richardson, Sr. This quick turnaround demonstrates that Edmondson was a pure speculator, not a settler—he invested his capital and, having found a buyer, took his profit.

The Legacy: William walked away with capital and experience—his first real stake in the New World that allowed him to transition from landless immigrant to established colonist. Meanwhile, Brinckloe, acting as the orchestrating agent, saw the entire deal through to completion in his official capacity as Clerk of the Court.

What This Means for Family History

This discovery completely reframes how I understand my ancestor. William Simson wasn't a failed landowner who lost his property through misfortune or poor judgment. He was a savvy immigrant who parlayed his one asset, his eligibility for a land patent, into the foundation for his American life.

The arrangement was actually quite common in the colonial period. Justice Brinckloe ran a land development business, using his political connections and capital to profit from the Duke of York's generous land policies. The story reveals three men playing their respective roles perfectly: William Simson, the immigrant who provided the name; John Edmondson, the wealthy speculator who provided the capital; and Justice John Brinckloe, the local man of affairs who managed every legal and logistical step of the venture.

The Power of New TechnologyThis discovery wouldn't have been possible without two key technological advances:

1. AI-powered transcription that made searchable text from handwritten 17th-century documents
2. AI research assistance that helped me understand the historical context and navigate complex digital archives

The combination of FamilySearch's expanding digitized collections with AI tools like Gemini has revolutionized genealogical research. What once would have required months of archive visits and specialized paleographic skills can now be accomplished from home.

Looking Forward

William Simson's story reminds us that our ancestors were often more sophisticated and opportunistic than we give them credit for. The colonial period was full of complex business arrangements, political maneuvering, and economic partnerships that don't always show up clearly in traditional genealogical sources.

As AI continues to improve document transcription and search capabilities, I suspect many more family mysteries like this one will be solved. The key is learning to ask the right questions and understanding that the first explanation for a genealogical puzzle isn't always correct.

I'm grateful to finally understand what happened to William Simson and his 400 acres. He didn't lose Simpson's Choice. He used it exactly as it was intended: as his ticket to a new life in America.