The Railroad Was There All Along
Tuesday June 03, 2025
Harry Lee Williams was born in August 1885 in Honey Creek Township, White County, Indiana. The son of Thornton Robert Williams and Ida May Adams, Harry was raised in a small rural town before eventually settling in Cincinnati, Ohio, where he would spend the rest of his life. He married Julia McNeal across the river in Covington, Kentucky, in 1907, likely taking advantage of the looser marriage laws there. Their first daughter was born in Cincinnati the following year, and by the time of the 1910 census, Harry was firmly rooted in Hamilton County.
Over the decades, Harry appeared regularly in census records: in 1910, 1920, 1930, and 1940, always living in Cincinnati’s Ward 19. He registered for both World War I and World War II drafts. He died there in February 1950 and was buried in Spring Grove Cemetery. There was no question about where he lived, worked, and raised his family. But one question persisted: what railroad did he actually work for.
Family lore offered two candidates. On one side, the Baltimore and Ohio (B&O) had long been part of family conversations. On the other, the Louisville and Nashville (L&N) came up more than once in old stories. Given Cincinnati’s deep ties to the rail industry and both railroads, both seemed plausible. The trail, however, came down to a single puzzling line on his World War I draft card, not in the employer section, as one might expect, but in the address field. The handwriting, looping and faded, looked like it might be a street address. I initially read it as something like “666 South Kentucky,” which made no geographic sense. It did not exist in Cincinnati or anywhere nearby. What seemed like a bad address gradually revealed itself to be something else entirely.
The breakthrough, or so it seemed, came from Harry’s World War I draft card. These cards are often rich with detail: names, addresses, occupations, even employers. But in Harry’s case, one particular line obscured more than it revealed.
The handwriting on the address line was cramped and inconsistent, with swooping loops that blurred the distinction between letters. I initially read the entry as “666 S. Kentucky, Chicago.” That interpretation would suggest a temporary work placement in Chicago, perhaps linked to a rail terminal or yard. It aligned neatly with family stories of railroad work, and Chicago’s prominence in the rail industry made the location plausible. But something about it was off.
Despite repeated searches through modern maps, historical directories, and databases of street names, there was no trace of a “666 South Kentucky” in Chicago. It did not correspond to any known depot, office, or neighborhood. The more I looked, the more it became clear that what I was seeing might not be an address at all.
The turning point came when I decided to bring in some extra help. I uploaded the draft card snippet into ChatGPT, hoping that a second set of eyes, artificial though they might be, could offer a new perspective. Together, we began to break down the writing, character by character.
That was when the first real shift occurred. The looping shape I had interpreted as “Kentucky” started to look a lot less like a place name and more like something else entirely. We noticed the two key letters at the end: “Ry.” In historical documents, especially employment records and correspondence from the early 1900s, “Ry” is a common abbreviation for “Railway.” Suddenly, the next part of the line, “Chicago Div”, fell into place as “Chicago Division.”
This was not an address. It was a railroad assignment.
The entire phrase was reframed: instead of “666 S. Kentucky,” we now had the structure “(Company) Ry, Chicago Div.” That realization opened a much wider field of inquiry. Historical railroads frequently abbreviated their names, especially when they linked multiple cities. Now, instead of chasing down ghost addresses, we were hunting for a railway company, and we finally had the right format to start asking better questions.
This mystery was not unraveled by accident. It was the result of a real collaboration, human reasoning paired with AI assistance, each sharpening the other. As we tested hypothesis after hypothesis, the lines between address and employer, street and abbreviation, began to blur. What had started as a search for “666 S. Kentucky” evolved into a layered analysis of historic railroad terminology, document handwriting, and corporate mergers.
The “aha” moment came when we both locked in on the handwriting and read it, definitively, as “CCC&StL Ry.” Not a street. Not a mistake. Not a ghost address. Just a perfectly normal employer, written in perfectly normal (if rushed) early-20th-century cursive. The Cleveland, Cincinnati, Chicago & St. Louis Railway.
Once we had that key, everything else held firm. The Big Four had a deep and lasting presence in Cincinnati. The Chicago Division operated through that region, serving freight and passenger lines across multiple states. And by the time Harry’s World War II draft card listed him as an employee of the New York Central, the corporate transition was complete. We had not just solved a handwriting puzzle. We had confirmed a historical continuity, tracing one man’s working life across decades, railroad companies, and changing names.
With the pieces in place, a fuller portrait of Harry Lee Williams’s working life emerges. Born in Indiana in 1885, Harry moved to Cincinnati by 1908, where he raised a family and built a career in the railroad industry. By the time he registered for the World War I draft, he was employed by the Cleveland, Cincinnati, Chicago & St. Louis Railway, the Big Four, assigned to its Chicago Division. That line eventually became part of the New York Central Railroad, where he continued to work into the 1940s, as confirmed by his World War II draft card. He remained in Cincinnati for the rest of his life, passing away in 1950.
This quiet, working life might have gone unremarked if not for a scribbled line on a government form. A few strokes of looping cursive turned out to contain a complete story, of economic migration, industrial change, and personal perseverance. The handwriting was not a flaw in the record. It was the record.
And solving it required a partnership. Human memory, historical knowledge, and digital tools each had a part to play. What began as a family question, “Which railroad did he really work for?” ended with a shared sense of discovery, where AI did not replace the researcher, but stood beside them. Together, we chased a name through time, and found the tracks it left behind.