Part 3: The People
George Drake, Jr.: Last time on Fifth and Ludlow…
George Drake, Jr.: We took the letter and envelopes out of the frame, and while there was nothing on the back of any of it, the envelopes fit together perfectly.
George Drake, Jr (on tape): “Well, it fits.”
Frank Hollingsworth: “It fits and the folds…”
George Drake, Jr (on tape): “Match up.”
Frank Hollingsworth: “Match up.”
George Drake, Jr.: Then Ruth started doing some digging into Rose and found that Will, the man who wrote the letter to her in 1920, may have been closer than we thought...
Ruth Reveal: “The exciting thing is that she had two boarders living in her house in 1930, Andrew and William.”
George Drake, Jr. (on tape): “Ohhhhhh!!”
Ruth Reveal: “Right?!”
George Drake, Jr.: I’m George Drake, Jr. and this is Fifth & Ludlow. Part 3: The People.
At this point it had been a few months since we started looking into Rose, Will, and Jim — and they were starting to feel more like people to me instead of just names on paper. They had lives in the city that I now call home. They walked down the same streets, they could have seen some of the same trees. I mean, Woodland Cemetery, which has been there since the 1840s — and where Rose is actually buried — has many trees that are over 100 years old, so it’s possible.
Then I started to wonder what life was like for them — were they at a good place financially leading up to the Depression? Did they ever make it out to Huffman Field to see the Wright Brothers fly their plane? What was it like the first time they ever drove in a car? Unfortunately, these are things that census records can’t answer — but that’s all we had.
We did also have this letter from Will that he sent to Rose. He wrote in a way that Rose would know exactly what he’s talking about, but to everyone on the outside, it’s vague enough to not be able to pin anything down. It says, “Friend Rose. I got your letter and I am well, and I hope this will please you, Rose. I will meet you at the corner of Fifth and Ludlow at Jenkin’s Drugstore at 7:30 and you and I will go out to the home and go some place to ourselves and talk the matter over. Hoping you will be all okay when we meet, if you are willing to do this and keep it to yourself. Will.”
Up to this point, we hadn’t found anything out about Will. But we did have a lead.
So, to go over where we left off, here’s what Ruth — my wife and partner in this podcast — found out from census records:
Rose — or at least the Rose we were looking into, which seems pretty certain to us at this point — had a daughter named Bertha who shared the last name of Wysong with her husband Harley. According to the census, they were both living in Rose’s house in 1930.
Rose also had a son named James who would have been 16 at the time.
According to that same census, Rose is a widow, but it doesn’t say her late husband’s name, so there’s a chance it might not even be the Jim from our envelope.
Finally, in 1930, Rose had two boarders staying in her home — one named Andrew, and another one named William — or, to us, “Will.” The same name as the guy who wrote the letter. There’s no way we can be sure if it’s the same guy, however, because we still don’t know Will-the-letter-writer’s last name.
Ruth Reveal: “So, it's William Hoffrichter is listed as her boarder. And in 1930 he's... it says he was 62 years old.”
George Drake, Jr. (on tape): “In 1930.”
Ruth Reveal: “In 1930. So, in 1920 he would have been 52. She would have been 37 in 1920 when the letter was written. Bertha was her first daughter. And she was only 16 when she had her. And then she had a son Ralph, and then a son James.”
George Drake, Jr. (on tape): “Okay, wait. So in 1930 James was 16.”
Ruth Reveal: “Yeah, so it doesn't really make sense to send a six-year-old a letter…”
George Drake, Jr. (on tape): “Right.”
Ruth Reveal: “...forwarded from Zanesville. So, then, like, when I was thinking about the letter and Will saying 'we'll go to the home,' I was like, if he was inquiring about getting a room at her house that would make sense. If he said ‘we'll go to the home’ like, 'the home where I'm going to live with you if I'm your lodger.'”
George Drake, Jr. (on tape): “But he was so secretive about it.”
Ruth Reveal: “I know. Well, he's also listed as a widow and she's listed as a widow. So, I don't know. Maybe he was like, embarrassed? I have no idea. But then there's this other boarder, Andrew Reedy. He was 76. I haven't looked him up yet. Let's see.”
George Drake, Jr.: So, she looked for Andrew Reedy in the census records and found a result — not from the 1930 census, but the 1920 census — and he wasn’t the only one listed there…
Ruth Reveal: “Oh, there he is! There's his, wait... (screams) There's Rose's husband James! So, Andrew, I went through Andrew Reedy's record. From the 1920 census in Dayton, James O'Connor is listed as the head of the household, age 53. Rose O'Connor, his wife, Ralph, his son, Clara, daughter, James, son. Five years old. That's when the letter would have been written. And then, and William is not listed as one of the boarders in 1920 the 1920 census! Oh my gosh, so, like, that's too many coincidences.”
George Drake, Jr. (on tape): “Yeah, it has to be... It has to be him.”
Ruth Reveal: “Jim has to be her husband and the letter was just forwarded to her husband, and apparently he was still alive in 1920.”
George Drake, Jr. (on tape): “So, he died in between 1920 and 1930.”
Ruth Reveal: “Yeah. Jim.”
George Drake, Jr.: In 1920, Jim is listed as a night watchman on the railroad — so it makes sense that the envelope addressed to him was sent to Union Depot.
One thing we noticed about the census records as a whole is that they’re wildly inconsistent. Spelling errors are frequent, ages fluctuate from one census to the next. That’s as far as we got.
Ruth Reveal: “It's lucky that Bertha and Harley still lived with them, because otherwise we wouldn't know that her name changed and then we would have no idea that they were related, even though they’re buried next to each other. But, like, Rose, I don't know. She seems like a cool lady. She had like, a lot of kids, two boarders living in her house. I just want to know where they lived.”
George Drake, Jr.: They lived at 18 S. Tecumseh — right in the heart of Dayton’s Oregon District.
Ruth really wanted Rose to have survived the 1913 flood. It’s one of those things true present-day Daytonians put on a pedestal — that the city came together as one and survived the flood, like they were there paddling the boats with them. Rose did. In 1913, they were living somewhere else in the Oregon District — where the flood waters would have been at some of their deepest. With that in mind, we weren’t even sure the house would still be there.
Either way, I put the address into the GPS.
Ruth Reveal: “So, was the address there?”
George Drake, Jr. (on tape): “Yep. It’s there, and we’re going!”
Ruth Reveal: “Exciting!”
George Drake, Jr.: For being one of the hardest-hit areas during the flood, the houses look great. If the house was made of brick, it’s most likely still standing today, and this area has brick houses on both sides of most of the streets. They’re original and they predate the flood.
Ruth Reveal: “1855?”
George Drake, Jr. (on tape): “That was the date, yeah...
Ruth Reveal: “Oh, oh!”
George Drake, Jr. (on tape): “...it was built. So, yeah, if it's here, it's definitely still standing.”
Ruth Reveal: “24...”
George Drake, Jr. (on tape): “20. It’s this one.”
Ruth Reveal: “It's so cute!”
George Drake, Jr.: It is a cute place. It’s turquoise in color with white shutters and maroon trim. It’s actually the right half of a double — so it has a mirror image of itself on the other side.
We knocked, but no one answered. So, I left my card along with an explanation of what I was doing and how I wanted to tour their house, not necessarily record them personally, but I never heard back.
Part of me wanted to experience the same thing I felt when I was in the bathroom of the Hollingsworth’s old house — that feeling of being so physically close, standing where they stood, maybe guessing who stayed in what room, wishing I could instantly time travel to see how they lived.
Just like last time, I didn’t think it would be enough. It would be a cool experience, but it wouldn’t lead anywhere or answer any questions. Ruth and I were having fun finally finding things out, and I didn’t want to lose that momentum. With that said, I never knocked on the door of 18 S. Tecumseh again.
Instead, I went a more practical route to find out information about the people in question.
Curt Dalton: “Curt Dalton. Visual resource manager for Dayton History.”
George Drake, Jr.: If you need to know anything about the history of Dayton — especially if there are records or anything like that to comb through — Curt is the guy to talk to. He’s not afraid to do some digging or get a little dusty.
To start, he looked into the two people from the front of the envelope addressed to Rose. Oscar Gilbert, who the letter to Rose was addressed to “in care of,” and JT Shafer — the one who signed the envelope “opened by mistake but not read.”
Curt Dalton: “Oscar Gilbert who's on the front of the first letter is the superintendent for the Krug Baking Company and then he lived with his wife Rosa at 1147 W. Second. So, that might be possibly why the letter was open. Because Rosa, Rose, with that bad handwriting, that could be because the gentleman who is James, this is James F. Shafer — that’s what it kind of looks like because it's initials — he also works as a baker at a bakery. And so, he was probably working for Mr. Gilbert, saw the ‘Rosa,’ opened it, and thought, ‘Oh, this isn't his Rose,’ and said ‘I didn't…’ I'm sure that's why he wrote the note, you know, ‘I didn't read this,’ because it’s against the law to open up someone else's mail.’”
George Drake, Jr.: Curt also looked into the people who built the house the Hollingsworth’s lived in. As they said, they’ve always speculated that the letter actually belonged to the people who built the house and not necessarily who lived in the house and paid for it to be built. And that may be true, because Rose and Jim definitely didn’t live there.
Curt Dalton: “It looks like, from everything I can find out, that a Dr. P.H. Kilbourne and his wife Ethel, and probably his mother, Mary, because it says 'widow,' are all living at 420 Ridgewood Avenue.”
George Drake, Jr.: That’s according to the 1928 city directory, which is the first year the house even shows up in a city directory. So, Curt said that establishes what we already knew — that the house was at least finished being built in 1927.
He didn’t dig too much into Kilbourne because he didn’t seem connected to Rose and Jim. He only learned that — around the time he completed construction on his house — he worked in room 740 of the Fidelity Medical Building downtown.
Curt then gave us a lot of the information we’d already found out about Rose and Jim from the census records — when they were born, their kids names, occupations, etcetera. He was able to see where they lived for the years in between when the census was taken by looking through city directories.
Then he dug a little deeper though and found something else.
Curt Dalton: “But more importantly is an ad that the newspaper, that appeared at least four times at that time, beginning just a little over a month after the letter has been written. The ad appears in the Dayton Daily News on August 16, 1920 for the first time on page 14 under the title ‘Personal Notices’ and it says 'I will not be responsible for any debts contracted by my wife Rose O'Connor.’ Signed ‘J O'Connor.’ Now, this appears another three times at least after that, and back then that's what you had to do legally when you were going to get a divorce.”
George Drake, Jr.: So, Will sent his letter to Rose on July 20th, 1920. Less than one month later, Jim takes out this ad in the paper — for four consecutive days — that basically says, “if my wife is out there running up tabs, this is my public notice that it is not my problem.” That alone seems to align with the “affair” narrative many have adopted for Rose and Will, but it may not actually be in the case.
Curt Dalton: “In ‘24 and ‘25 the O’Conners were still living together. So, more than likely they didn't get a divorce. You could take the time to look at divorce records back then and see if they filed, because they kept records even if they don't go through with it, but more likely changed his mind. Okay? The strange thing is that in 1926 Rose is still living out at S. Tecumseh Street, but James isn't there, but he's also not dead. So there's two possibilities: he finally got fed up and left, or he got sick.
George Drake, Jr.: Now, moving onto 1930 — the first time Will enters our story.
Curt Dalton: “In 1930 Rose is now listed as a widow of James, which is why I do not believe they got a divorce, but normally if they had gotten a divorce she wouldn't have been his ‘widow.’ So, William Hoffrichter, I guess, is also listed as a widow. Widower, I guess, but they say 'widow.’ Age 62 so, you know, that's that's when they finally started putting down if you were married, divorced, widowed, etcetera. So at one time he had been married to somebody, at least one person, but I've never seen any records of it.”
George Drake, Jr.: Will was as a machinist working with farm lighting, which Curt says was most likely Delco Light — the biggest player in electricity in Dayton at the time. Delco opened up shop in 1916. Because many homes and businesses within the city already had electricity, Delco looked outward toward the rural areas — like the farms — to make it so they didn’t need to rely on oil lamps and lanterns. That is what Will helped with.
George Drake, Jr.: We went from knowing the pretty on-the-surface stuff about Rose, Jim, and Will to knowing some relatively intimate details — all with public records nonetheless.
After our conversation with Curt, Ruth and I were talking through what we learned in the car on the way home, and she brought up one important thing we’d overlooked when discussing the classified ad that Jim took out in August 1920 — the second envelope.
So, the letter Will sent to Rose was maybe forwarded to Jim in 1921, but a year after she received it. So, it’s not likely that the letter was the reason why he took out the ad because he didn’t even see it yet.
Ruth Reveal: “If James had somehow found out that something was going on, then just a month later, after Rose met Will, he filed those things in the newspaper. But he wouldn't have had like, physical evidence... someone must have told him or she told him or something.”
George Drake, Jr.: Now, don’t get me wrong, Curt finding this ad is exciting — pieces were starting to come together, but in a sad way. As I said before, we were starting to feel attached to the people in this story. So, while this news of Jim’s ad definitely made for a nice element, we didn’t necessarily want there to be marriage troubles. On top of that, Ruth and I were kind of disappointed that our admittedly somewhat mundane speculations about Will being a boarder weren’t confirmed.
Ruth Reveal: “I have been convinced now that it was just a totally harmless, like ‘I want to be a boarder in your house.’ And so when he said he had a newspaper ad, I thought for sure it was an ad…”
George Drake, Jr. (on tape): “Yeah I did too!”
Ruth Reveal: “Yeah — for renting a room in their house. I did not expect that it would be an ad that James was like, ‘I do not…’”
George Drake, Jr. (on tape): “Right. Right.”
Ruth Reveal: “‘I'm not responsible for my wife.”
George Drake, Jr. (on tape): “Yeah, I thought the same thing.”
Ruth Reveal: “Yeah, and I was excited. I was like, ‘oh, that's perfect.’ Like, ‘then we have evidence that that was their relationship.’”
George Drake, Jr. (on tape): “It'll tie that bow on it.”
Ruth Reveal: “But it's not. I mean — and he seems, also, like everyone else we've talked to, to think that there was something romantic going on.”
George Drake, Jr. (on tape): “Yes, exactly!”
Ruth Reveal: “Like, every single person.”
George Drake, Jr. (on tape): “And you’d think he would be the one person that would be like…”
Ruth Reveal: “Right. Like, ‘oh no…’”
George Drake, Jr. (on tape): “...very factual, like, ‘do not,’ kind of, ‘make your own assumptions about people.’ But he assumed so much!”
Ruth Reveal: “I know.”
George Drake, Jr.: While in the car, we decided to head to Rose’s house and make the walk to the corner of Fifth and Ludlow where she was supposed to have met Will. I admit, partly for that “standing where they stood” aspect, but also for a better feeling on timing.
George Drake, Jr. (on tape): “Alright. So, which way would Rose have gone from here?”
Ruth Reveal: “She would have walked out her door and gone right… And then, we’re approaching Sixth Street. She would have turned left on Sixth Street.”
George Drake, Jr. (on tape): “Okay.”
George Drake, Jr.: The walk to where Jenkin’s Drug Store once stood is pretty much the same as it would have been back then, in the 1920s — the streets have the same layout and many of the buildings along the way are the same — but it’s probably less crowded. Parking is easy to find in Dayton today — even on a weekend — but the pictures I’ve seen of the city from the 1920s, there are black cars lining the streets like a wall on both sides, and the sidewalks seem more crowded, too.
Just over halfway there, oddly enough, we passed the Fidelity Medical Building — which, if you remember, is where Dr. P.H. Kilbourne worked. He’s the man who built the house that would act as the time capsule for Will’s letter.
Ruth Reveal: “So, that’s really close!”
George Drake, Jr. (on tape): “Yeah. That’s such a small world!”
Ruth Reveal: “Well, Dayton is a small city.”
George Drake, Jr.: We arrived at the corner of Fifth & Ludlow, where Jenkin’s Drug Store once stood, in a little under eight minutes. When we got there we had to confirm which corner was the right one.
Ruth Reveal: “Okay. It was the northeast corner of Fifth and Ludlow.”
George Drake, Jr. (on tape): “So it was this one. This corner here?”
Ruth Reveal: “Is this northeast?”
George Drake, Jr. (on tape): “That corner.”
Ruth Reveal: “Well, let’s cross!”
George Drake, Jr. (on tape): “Alright.”
George Drake, Jr.: The building that stands on the corner is five-stories tall and is known as the Ludlow Building. It’s actually three buildings disguised as one — the two three-story buildings on each side also make up part of the structure. It was built in 1917, and there’s photographic evidence that Jenkin’s Drugstore was there in a different building during the flood in 1913, as well as on the ground floor of the Ludlow Building. So, Jenkin’s must have moved out during construction and then back in sometime after it was completed.
Jenkin’s had four locations around Dayton. They sold everything from antiseptic shampoo and cigars, to ivory toilet articles and candy.
I’ve seen this building dozens of times — I even cupped my hands to take a look inside a few years ago because it was vacant at the time. It’s never really meant anything to me, to be honest, outside of the fact that I thought it was sad that such a pretty building was empty. But I see it in a different light now — especially because it looks the same as it did back then. It’s the building where Rose and Will could have met.
George Drake, Jr.: A few months went by, and during that time Ruth and I spent our first anniversary in the quaint little town of Bellville, Ohio. When we got off the highway to make our way to our hotel, we drove past the Ohio Genealogical Society. We’d been meaning to go there but this was completely on accident. So, we pulled out my phone to record because I didn’t bring my kit, and stopped in to comb through some records.
Ruth Reveal: “‘I just want to point out, for posterity’s sake, that we are currently on our first anniversary getaway, sitting on the floor of the Ohio Genealogical Society reading cemetery records. Wysong, okay.”
George Drake, Jr.: We left empty handed. It basically had everything Curt had already told us. Also, because census records are sealed for 72 years after information is collected to keep peoples’ information private, we were unable to follow Rose and her children past the mid-1940s or so.
And, unfortunately for me, that’s what I determined I needed to do next: somehow find my way into that 72 year gap and track down a descendant of Rose, Jim, or Will to help shed some more light on what this letter could be about.
Before I started to cold call all the O’Connors and Wysongs in the phone book, I decided to try something easier first — I made an image that read “Podcast producer seeking descendants of Daytonians for series on local mystery,” included the names of the people I was looking into, and how to get in touch with me. I posted it on Facebook as well as Craigslist personals in a few major Midwestern cities.
I had more luck on Facebook. Within a day the image was shared over 100 times (which is a lot for my social media use). Then, a woman named Jessi Sievers reached out directly.
Jessi Sievers: “I love connecting people to their history and I love the stories that you find when you do — the stories are my thing. I really like stories so... So I'm not a professional, like, that's that's the takeaway here. I am not a professional. This is, like, I take what I find, I can give you facts, I can sort of interpret, but, you know, I'm not a professional.”
George Drake, Jr.: She’s an amateur genealogist and has looked into everything to do with herons family’s past, as well as the families of some of her friends. She has accounts with a few online databases — including Ancestry.com — and uses them to the fullest extent. She said, on Ancestry, people can upload their own family trees on there to help fill in any blanks, and that they can either make them private or visible to the public…
Jessi Sievers: “And someone — one tree — had all of these people, and this like — nobody else was doing this family, or something. I'm not sure but… we could see if maybe we could get in touch with them.”
George Drake, Jr. (on tape): “They very well might be the only person.”
Jessi Sievers: “They could yeah, they... yeah.”
George Drake, Jr.: To see a map showing the 1913 flood, Jim’s ad in the classified section, Rose’s house as it is now, some ads from Jenkin’s Drug Store, and what the corner of Fifth & Ludlow looked like in the 1920s, visit the website, www.fifthandludlowpodcast.com.
There you can also find the show on TuneIn and other outlets to subscribe to the podcast.
If you have time, I’d appreciate if you took a moment to rate and review the show wherever you listen to it. Those stars and short reviews go a long way in getting Fifth & Ludlow heard by more people and moving it up in the rankings.
Theme and other music used in Fifth & Ludlow is by Mustafa Shaheen.
Logo and branding is by Peter Diaczenko.
This series is made possible by a generous grant from the Montgomery County Arts & Cultural District with assistance from Culture Works.
Additional funding is from 91.3 WYSO.
Episode editor is Katie Davis. Additional content assistance from Ruth Reveal and Craig Shank.
Special thanks to the Hollingsworth Family, Curt Dalton, Dayton History, the Ohio Genealogy Society, and Jessi Sievers for their help with this episode.
I’m George Drake, Jr. Thanks for listening to Fifth & Ludlow.
George Drake, Jr.: Next time on Fifth & Ludlow…
Jessi Sievers: “So this was in October 10th of 1928 in the Dayton Herald: ‘Rose O'Connor, 405 Brown Street, charges James O'Connor of Dayton with willful of absence for three years past.’”
Jessi Sievers: “Vicky is her name, The owner of the tree, and her mother would be Clara’s youngest daughter. She is still living.”
George Drake, Jr. (on tape): “Wow! What?!”
Jesse Sievers: “Yes!”
George Drake, Jr. (on tape): “She seemed a little hesitant about stuff, and she has, I would like to say ‘request,’ but it is actually more of a demand.”
Kathy Hollingsworth: “Okay.”