52 AI Ancestors in 52 Weeks: Week 5: Challenge

I’ve combined Amy Johnson Crow’s 52 ancestors in 52 weeks challenge, and Steve Little’s The 2025 AI Genealogy Do-Over, to create a unique 52 AI ancestors in 52 weeks party!

52 AI Ancestors in 52 Weeks: Week 5: Challenge

Introduction

Week 5 of the 52 Ancestors challenge invites us to reflect on challenges—those faced by our ancestors or ones we’ve encountered in uncovering their stories. For me, the word “challenge” instantly conjures up my second great-grandmother, Theresa Kilkenny Anderson. Her story is one of resilience, quiet strength, and perseverance in the face of obstacles.

Meet Theresa Kilkenny Anderson

Theresa was born around December 1851 in Ireland, a time marked by the devastation of an Gorta Mór (the Great Hunger). Imagine the courage it took to survive, let alone emigrate to a new country under those circumstances. By the time she arrived in the United States—probably in New York—she was likely young, perhaps alone, and determined to build a new life.

Theresa married Michael Anderson by about 1872, and the couple welcomed children at a steady two-year rhythm. But their firstborn’s apparent early death foreshadowed the difficulties to come. The most crushing blow arrived in 1883, when Michael passed away suddenly at just 31 years old, leaving Theresa widowed with five small children and one on the way. Their daughter, Mary Frances, born later that year, also died young.

By 1900, Theresa was listed as a laundress in the U.S. Census, a widow, supporting her three children remaining at home. Her story is one of survival against the odds—a testament to fortitude and self-reliance in a time of few social safety nets.

The FAN Club: A New Research Angle

Researching Theresa’s life has not been easy. Despite her bravery, records of her early years remain elusive. I’ve struggled to find her FAN Club (Friends, Associates, and Neighbors)—a genealogist’s go-to method for piecing together an ancestor’s story.

That’s where AI entered the picture. Inspired by Theresa’s perseverance, I decided to give her story a boost by asking AI for help. Could technology uncover what traditional methods have not?

AI to the Rescue: Building Theresa’s FAN Club

When I shared Theresa’s story with ChatGPT, it suggested a methodical approach to reconstruct her network. The AI offered me a plan for identifying potential connections to her origins or her life after immigration. Here’s a taste of what it suggested:

  1. Passenger Lists and Ship Manifests
    • Objective: Identify fellow passengers who might have traveled with Theresa to the United States.
    • AI Support: Use name variation searches, contextual filters (e.g., age, gender, and nationality), and clustering tools to pinpoint people with similar migration paths.
    • Next Step: Search for Irish immigrants on the same ships arriving around the presumed timeframe of her immigration.
  2. Community and Church Records
    • Objective: Locate Theresa in New York parish records, which may reveal connections to other Kilkennys or Andersons.
    • AI Support: Analyze patterns in names and locations in digitized parish records to identify clusters of families or potential sponsors.
    • Next Step: Narrow down parishes near her residence in the census years.
  3. City Directories and Neighbors
    • Objective: Investigate Theresa’s neighborhoods for familiar surnames.
    • AI Support: Cross-reference census and city directory entries with Theresa’s address to identify potential friends or family nearby.
    • Next Step: Build a map of her social and geographic proximity to other Irish immigrants.
  4. DNA and Genetic Genealogy
    • Objective: Use DNA matches to piece together Theresa’s family tree.
    • AI Support: Generate hypotheses about familial relationships using shared matches and clustering tools.
    • Next Step: Collaborate with DNA cousins to uncover connections to Kilkenny or Anderson relatives.

A Fresh Perspective

As a genealogist, I tend to work in a process-driven way, and I was thrilled when AI offered clear “next steps.” It wasn’t just about data—it was about taking actionable strides in the right direction. AI’s support reminded me that while I may not have all the answers today, each clue brings me closer to understanding Theresa’s story.

Tracking Theresa’s FAN Club with AI and Spreadsheets

To systematically uncover Theresa’s network, I created a spreadsheet to track potential connections across different sources. Each worksheet represents a distinct research category:

  • Census Records: I recorded all indexed individuals from FamilySearch on the same census page as Theresa, plus three pages before and after (this is just a copy/paste from FamilySearch, NOT a transcription of my own).
  • Passenger Lists: I extracted the full list of steerage passengers from Theresa’s likely immigration record to identify potential travel companions (also a copy/paste).
  • Baptismal Sponsors: Once I obtain Theresa’s children’s baptismal records, I will add the sponsors to see if their names appear elsewhere in her life.

Once the data was organized, I turned to AI tools for assistance. First, I asked Copilot:

“Look at the names on the Immigration worksheet. Tell me which of these names occur on other worksheets, and where.”

Unfortunately, it wasn’t able to process the request effectively. However, when I posed the same question to ChatGPT, it successfully identified overlapping names across different sources—giving me valuable clues about possible relationships.

While I didn’t find immediate breakthroughs with those two people, this exercise confirmed that AI can assist in detecting patterns and connections that might be overlooked in manual research. The next logical step is to focus on the baptismal records, where sponsors might provide the missing links to Theresa’s origins.

Summary and Next Steps

Theresa Kilkenny Anderson is more than a name on a page. Her life is a reminder that even in the face of unimaginable adversity, strength and determination can carry us forward. By tapping into AI tools, I’m reinvigorating my research and finding new ways to honor her legacy. My focus now is uncovering her FAN Club and exploring potential connections to Ireland.

Challenge for Readers

Who’s the “challenging ancestor” in your tree? Is it someone who overcame incredible odds, or someone whose story remains an enigma? Use Theresa’s story—and the AI tools I’ve explored—as inspiration to tackle those brick walls. Share your journey in the comments!

Figure 1 Michael Anderson, Theresa’s son and my great grandfather


52 AI Ancestors in 52 Weeks: Week 4: Overlooked

52 AI Ancestors in 52 Weeks: Week 4: Overlooked

Introduction

Week 4 of the 52 Ancestors challenge dives into the overlooked. “Who is someone in your family tree who you haven’t researched very much?” It didn’t take any time for me to come up with the name: Andrew Driskol.

52 AI Ancestors in 52 Weeks: Week 4 – Overlooked

Introduction

Who in your family tree have you overlooked? For me, it’s Andrew Driskol. Or, rather, Andrew “Does-He-Even-Exist?” Driskol. He’s a puzzle—a man whose shadow falls across family records but refuses to leave a solid footprint. One of my very first finds as a baby genealogist was the marriage record of his daughter, my great grandmother, which listed his name. But as I dug deeper, the trail went cold. This week, I decided to tackle Andrew’s mystery with the help of a modern-day Watson: artificial intelligence.


Andrew Driskol: A Ghost in the Records

Andrew’s story—or lack thereof—begins in the 19th century, when civil and church records were often kept. The absence of documentation for someone like Andrew is unusual because his life spanned eras and locations where detailed records typically existed. This gap raises questions about whether his name was misspelled, misrecorded, or lost in migration. when civil and church records were often kept. He was likely born in Prussia, possibly Hesse-Darmstadt, around the 1830s or 1840s. He presumably married Malvina Hendell in England before emigrating to the United States in the 1870s. But here’s the kicker: there’s no direct record of Andrew. Not a birth certificate, not an immigration record, not a census entry. Yet, his children’s records consistently name him as their father.

The hunt for Andrew is a genealogist’s equivalent of chasing a will-o’-the-wisp. And yet, his legacy lives on in the scattered records of his children, like breadcrumbs leading nowhere. With AI in the picture, though, I wondered if I could piece together these fragments into something more substantial.

Figure 1 Anna Driskol Anderson ca 1914


My Data

I created a table of information I’ve gathered about him, all from records of his children; names:

Parents’ names as per childrens’ vitals

ChildMarriage YearMarriage Parents ListedDeath YearDeath Parents Listed
EdwardNot foundNot applicableNot foundNot applicable
Mary1891Andrew Driskoll M. Hendell1938Andrew Driskol (Ger) Malvina Helda (Ger)
1926Andrew Driscol Malvina Henall
Josephine1899Andrew Driscoll Melvina Hendel1925Andrew Driscoll (Ger) Malvina _endels (Ger)
Anna1906Andrew Driskol Malvina1922Andrew Driscoll (Ger) Malvina Driscoll (Eng)
JosephNot foundNot applicable1925Andrew Driscoll (Ger) Malvina Hendell (Eng)

I also created a table of places of birth, since there is a little variation:

Census parents’ places of birth (child/father/mother)

Child1900 census1910 census1920 census1930 census
EdwardGer/Ger/Ger   
MaryNY/Ger/EngNY/NY/NYNY/Ger/EngNY/Ger/Eng
JosephineNY/Ger/GerNY/Ger/EngNY/PRUS-Ger/PRUS-Ger 
AnnaNY/Ger/GerNY/IRE/GerNY/Ger/Ger 
JosephNY/Ger/GerNY/Ger/Eng  

I’ve created a timeline for him:

Timeline for Andrew Driskol

  • ca. 1830s – Andrew Driskol is born, perhaps in Prussia and/or Hesse-Darmstadt, Germany.
  • by 1864 – He migrates to England and (presumably) marries Malvina Hendell.
  • ca. 1864 – His son, Edward, is born in England.
  • ca. 1866 – His daughter, Edith, is born in England.
  • by 1875 – Andrew immigrates to the United States.
  • 1875 – His wife Malvina and their children arrive in the United States, probably joining him.
  • 1873 – A child is born in New York [sic].
  • 1878 – Another child is born in New York.
  • 1880 – Another child is born in New York. Andrew and family are not located in the 1880 census.
  • 1883 – Last known child is born in New York.
  • 1890 – Had Andrew died by now, as his son purchased land?
  • by 1900 – Andrew Driskol dies, as Malvina is listed as a widow in the census.

I’ve not been able to locate him and every so often, I track him for a while, encounter the same nonanswers, and give up again for a time.

My AI-Assisted Research Plan

Using AI tools to analyze my data, I created a structured research plan.

Using the three tables in the attached (parents names as per childrens’ vitals, census parents places of birth, and timeline, create a research plan for Andrew Driskol.             

<I attached a document with the three tables above>

It replied with a research plan, containing a research objective, timeline hypothesis, research goals, specific research steps, analysis and documentation, and further considerations:

Research Plan for Andrew Driskol


Research Objective

To confirm the life events of Andrew Driskol, including his birth, marriage, immigration, and death, and to verify family relationships and origins through vital records, census data, and immigration documents.


Timeline Hypothesis

  • <not reproduced here; it was really the timeline above>

Research Goals

  1. Locate Vital Records:
    1. Birth record (Prussia, ca. 1835–1840).
    1. Marriage record (possibly England, ca. 1860–1865).
    1. Death record (United States, ca. 1890).
    1. Children’s vital records to confirm parentage.
  2. Investigate Immigration:
    1. Ship manifests for Andrew, Malvina, and children.
    1. Naturalization records for Andrew.
  3. Census Records:
    1. Locate Andrew and family in the 1870 and 1880 U.S. censuses.
    1. Review 1900 and later censuses for children to verify reported parent birthplaces and relationships.
  4. Confirm Parentage and Origins:
    1. Cross-reference children’s marriage and death certificates for consistency.
    1. Explore German and Prussian records for potential leads.
  5. Community and Local Records:
    1. Staten Island and NYC directories or church records.
    1. Burial records or cemetery listings.

Specific Research Steps

Step 1: Census Research

  • Goal: Locate Andrew in 1870 and 1880 censuses and confirm family details.
  • Strategy:
    • Search for “Andrew Driskol” with variations (e.g., Driscoll, Driscol) in New York City and Staten Island.
    • Explore neighboring areas for missed or misindexed records.

Step 2: Immigration Records

  • Goal: Confirm immigration details for Andrew, Malvina, and children (1868–1875).
  • Strategy:
    • Search passenger lists on major databases (e.g., Ancestry, FamilySearch) for ships arriving in New York.
    • Check manifests for individuals born in Prussia, traveling with family.

Step 3: Vital Records

  • Goal: Obtain key documents to confirm relationships and dates.
  • Strategy:
    • Search NYC vital records for Andrew’s death record (ca. 1890).
    • Obtain marriage certificates for Mary (1891, 1926), Josephine (1899), and Anna (1906).
    • Acquire death certificates for Josephine (1925), Anna (1922), Joseph (1925), and Mary (1938).

Step 4: European Records

  • Goal: Identify Andrew’s origins in Prussia and confirm marriage details in England.
  • Strategy:
    • Search Prussian birth records (1835–1840) using German archives or online resources.
    • Investigate English marriage records (1860–1865) for Andrew and Malvina.

Step 5: Community and Church Records

  • Goal: Supplement missing information with local data.
  • Strategy:
    • Explore Staten Island directories, church baptismal records, and cemetery logs.
    • Check for obituaries or probate records in local archives.

Analysis and Documentation

  • Focus Areas:
    • Reconcile discrepancies in children’s vital records (e.g., variation in mother’s maiden name: Hendell, Helda, Henall).
    • Note inconsistencies in census parentage (e.g., Germany vs. Ireland vs. England origins).
    • Track potential family movement between census years.
  • Tools:
    • Timeline to track findings against the hypothesis.
    • Research log to document sources and results.

Further Considerations

  • If records are inconclusive, pursue DNA testing with known descendants to confirm connections.
  • Collaborate with online genealogy communities for fresh insights or rare record access.

AI’s Role in Clarity

AI didn’t magically find Andrew hiding in a forgotten archive (though I wished for that). Instead, it helped me organize my research into actionable steps and avoid the dreaded rabbit holes. By using tools like ChatGPT for brainstorming and database-specific AI search assistants, I was able to identify patterns, generate alternative search strategies, and refine my focus on critical records. ChatGPT didn’t help much with creating a timeline, but Dana Leeds encouraged me to try it with Claude. This structured approach keeps me grounded as I continue the search.


Summary and Next Steps

Artificial Intelligence is actually a really good way to ground the genealogist who tends to dive down rabbit holes (not that I do that, wink wink).

For Andrew, the search continues. My next steps are to delve into European records, seek out local church and burial data, and perhaps even explore DNA testing with descendants. Andrew may be a ghost in the records, but with persistence and a little AI assistance, I’m determined to uncover his story—or at least understand why it’s missing.


Challenge for Readers

Who’s the most elusive ancestor in your tree? Apply these research strategies to uncover their story. For example, try creating a timeline of what you already know about your ancestor. Highlight gaps where records are missing and focus your searches on those areas. This simple step can make your research more efficient and targeted. Start by organizing what you know, then create a clear plan using actionable steps like those above. AI tools can help you stay on track and think critically.


52 AI Ancestors in 52 Weeks: Week 3: Nickname

I’ve combined Amy Johnson Crow’s 52 ancestors in 52 weeks challenge, and Steve Little’s The 2025 AI Genealogy Do-Over, to create a unique 52 AI ancestors in 52 weeks party!

52 AI Ancestors in 52 Weeks: Week 3: Nickname

Introduction

Week 3 of the 52 Ancestors challenge dives into nicknames. “Which of your ancestors had a nickname? Do you know how they got it?”

This week, I’ll step away from my maternal grandmother’s line to focus on my paternal grandmother’s mother, my great-grandmother Mary Agnes HART CAREY (1892-1978) —known to us as “Nanny.”

Background

Great Grandma, “Nanny” we called her, was named Mary Agnes HART CAREY. She was born, you might have guessed, into an Irish Catholic family.

The nickname

Her formal name, Mary Agnes, seemed typical for her heritage and era, but it also carried a hidden twist: she was universally called “Aggie.”

My grandmother shared how, after Nanny passed, she was shocked to learn her mother’s first name wasn’t actually “Agnes.” Nanny named one of her children “Agnes,” but not “Mary,” indicating how she wanted to leave the name behind.

Nicknames like “Aggie” often reflect personal preferences, family traditions, or even community influences. But what’s fascinating is how these seemingly small details offer insights into how ancestors presented themselves to the world or were seen by others.

Figure 1 Mary Agnes HART CAREY, date perhaps 1940s to early 1950s

The AI Connection: How AI Can Help Decode Nicknames

Nicknames can be tricky in genealogy, especially when records use formal names instead of the name your ancestor was commonly called. AI tools can be a game-changer here by offering innovative ways to trace and decode these hidden connections:

  1. Name Matching in Records
    AI-powered genealogy platforms can identify patterns in historical records, connecting nicknames to formal names. For example, searching for “Aggie” might yield records for Mary Agnes, even if “Aggie” isn’t explicitly listed. AI algorithms that analyze phonetic similarities (like the Soundex system) make this possible.
  2. Document Analysis
    Some AI tools can scan personal letters, diaries, or even old newspapers to detect nicknames alongside formal names. This can help clarify how nicknames were used and even uncover clues about their origins.
  3. Family Tree Suggestions
    Platforms like Ancestry.com and MyHeritage use AI to suggest connections. If an ancestor was known by different names in various documents, AI can consolidate the data, revealing hidden patterns or relationships you might otherwise miss.
  4. Cultural Context Insights
    AI can also analyze naming trends by era and region. For instance, “Aggie” as a nickname for Agnes was more popular in Irish communities during certain periods. Understanding these trends can make your ancestor’s story richer and more relatable.

Going Forward

What about you? Who in your family had a nickname that stood out? Did it reveal a personality quirk, a fond memory, or a cultural connection?

Take this week’s challenge to the next level by pairing your research with AI tools. You might discover a nickname hiding in plain sight or uncover how a loved one’s identity evolved over time.

52 AI Ancestors in 52 Weeks: Week 2: Favorite Photo

I’ve combined Amy Johnson Crow’s 52 ancestors in 52 weeks challenge, and Steve Little’s The 2025 AI Genealogy Do-Over, to create a unique 52 AI ancestors in 52 weeks party!

52 AI Ancestors in 52 Weeks: Week 2: Favorite Photo

Introduction

Week 2 of the 52 Ancestors challenge dives into your favorite photo. “Photos capture our family history like few other things can,” right? Picking a favorite is tough—I have a handful that hold deep meaning for me. Let me share one particularly special image with you: a portrait I labeled “Unknown Sailor.”

Background

My maternal grandmother, whom I wrote about last week, lost her mother at the age of three. As the only daughter, she inherited a collection of keepsakes, including a stack of photographs—most of them frustratingly unlabeled. One photo, though, stood out:

A sepia-toned image of a confident sailor, standing tall with an unmistakable pride.

This sailor seemed to radiate pride and confidence, but who was he?

The search

At first, I had no clues to identify him. Then, while researching Grandma’s maternal grandmother, Alice, I learned Alice had three brothers who served in the Civil War, including one in the Navy. That gave me a potential name: Oscar Smith.

For years, Oscar remained an enigma. No evidence could prove his identity. Then one day, while exploring collateral research, I connected with another genealogist studying the surname of Alice’s first husband (I descend from the second), my second cousin once removed. We compared notes and decided to meet, each bringing our family photo collections.

Imagine my surprise when she produced the exact same [unlabeled] sailor photo! Together, we became convinced the sailor was indeed Oscar Smith. Over a century after his naval service, Oscar had unwittingly brought two branches of our family back together.

Kathie and I corresponded and collaborated for quite a while. I assume she is now asking Alice for family information.

The AI connection

Here’s where modern tools entered the picture. Steve’s Photograph Analysis, a custom GPT from Steve Little, became my new research ally. I uploaded the sailor photo, and the AI provided a detailed analysis:

  • Composition: Lighting, subject placement, and atmosphere.
  • Context: Potential date, location, and even identity clues.
  • Insights: Surprising details about the photo’s timeline.

To my amazement, ChatGPT placed the photo in a time frame after Oscar had died. Was my theory wrong? Or was there a misstep in the analysis? This unexpected twist turned the photo into a deeper mystery, one I’m still unraveling.

Summary report including conclusion that the photo is from the early 1900s.

Going forward

I have my theories, but as any genealogist knows, personal beliefs don’t meet the Genealogical Proof Standard. For now, Oscar’s (?) photo remains a tantalizing puzzle. Who knows—maybe future 52 Ancestors prompts will give me the chance to share updates as this story unfolds.

Try it yourself

Curious about your own family photos? Give Steve’s photo analyzer a spin, or prompt an AI tool yourself to uncover hidden details in your family’s history. Happy hunting!

52 AI ancestors in 52 weeks: Week 1: In the Beginning

52 AI ancestors in 52 weeks: Week 1: In the Beginning

I’ve combined Amy Johnson Crow’s 52 ancestors in 52 weeks challenge, and Steve Little’s The 2025 AI Genealogy Do-Over, to create a unique 52 AI ancestors in 52 weeks party!

History says I won’t do it every week. But we’re talking about progress, not perfection. So, let’s just jump in and have fun.

52 AI Ancestors in 52 Weeks: Week 1: In the Beginning

Genealogy is like solving a family mystery—part detective work, part heartfelt storytelling. Throw AI into the mix, and it’s a whole new level of discovery. This year, I’m taking up a challenge that blends Amy Johnson Crow’s “52 Ancestors in 52 Weeks” with a techy twist inspired by Steve Little’s “The 2025 AI Genealogy Do-Over.” The goal? To explore both my family’s roots and the potential of AI in genealogy. Let’s kick it off with Week 1.


Why I Got Started

My genealogy obsession began in 6th grade when I got an assignment to create a family tree. Lucky for me, my grandmother—my biggest cheerleader—was just a few steps away. She dug out old records, shared stories, and filled in the gaps with amazing details. Thanks to her, I didn’t just complete the assignment; I caught the genealogy bug for life.

Grandma’s love for family history had its own story. She lost her mother at the tender age of three, and I believe her passion for genealogy was her way of reconnecting with that lost connection. She came from a prominent local family but struggled to tie certain pieces together. Those mysteries drove her—and now, they drive me.


The AI Connection

Fast forward to today. I’ve got tools my grandmother couldn’t have dreamed of—AI among them. This week, I gave an AI model a task: review and rewrite a tribute I wrote for my grandmother. Here’s how it went:

  • Step 1: I asked the AI to evaluate my tribute’s emotional resonance and clarity.
    • Please create guidelines for writing a tribute on the Internet, rate my page according to them, make suggestions, rewrite using the suggestions, and regrade. The page:
  • Step 2: I pasted the text (AI and links don’t always get along) and let it suggest edits.
  • Step 3: After trying a few models, Gemini delivered the most heartfelt rewrite. I put it below this post. What do you think? Let me know in the comments!

AI didn’t just polish the words—it helped me reflect on the way I’d captured my grandmother’s story. But, as powerful as AI is, it didn’t replace my voice; it enhanced it.

Grandma holding me at what was probably my first birthday


Your Challenge

Genealogy is personal, but technology can make it interactive. Here’s how you can join the journey:

  1. Pick an Ancestor: Choose someone in your family tree who inspires you. Write a short tribute to them (just 300 words or so).
  2. Add AI to the Mix: Use a free AI tool to refine your writing. ChatGPT, Claude, or Gemini are great options.
  3. Compare and Reflect: Does the AI version improve your story, or does it miss the mark? Adjust it to reflect your voice.

Share your experience in the comments—I’d love to hear how AI shapes your family’s stories.


In the End, It’s All About Connection

Genealogy and AI might seem like an odd pairing, but at their core, both are about uncovering connections. Whether it’s piecing together family lore or fine-tuning a tribute, every little discovery brings us closer to understanding who we are.

Here’s to Week 1—and to Grandma, who started it all. Without her, this journey wouldn’t be possible. And thanks to AI, it’s more exciting than ever.


Final Thoughts: Technology can amplify the past, but it’s the stories we share that keep it alive. So here’s my challenge: embrace both the wisdom of your ancestors and the tools of today to create something truly timeless.

The AI-revised tribute:

A Tribute to Edith Lillian Makey West (1913-1997)

Edith Lillian Makey West, my beloved Grandma, was born on September 12, 1913, in Staten Island, New York. Her life, though marked by early loss – her mother passed away when she was just three years old – was a testament to resilience and love.

Raised by her strong and loving [Janet adds: aunt, her namesake Edith, and] stepmother, Elfrida, Edith grew into a vibrant young woman. She graduated from Bryant High School and embarked on her career, working first as a candy packer and then for The Corporation Trust Company, where she dedicated many years.

Edith and my Grandpa, Gordon, shared a deep and enduring love. Their marriage, celebrated in 1935, was a cornerstone of her life. They traveled extensively, exploring 37 states together, and cherished raising their children, Alan and Elise.

Grandma’s passion for family history ignited my own. Countless hours were spent discussing ancestors, sharing stories, and piecing together our family’s past. Her excitement was contagious, fueling my own genealogical pursuits.

More than anything, Grandma embodied strength and resilience. She faced life’s challenges with grace and determination, inspiring me with her quiet strength.

Though she is gone, her memory lives on. I will always cherish the warmth of her smile, the comforting sound of her laughter, and the enduring lessons she imparted.