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:

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.

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!