I am in much disillusion after many months of research, turning up almost nothing, on a composer from the early 1900s who went onto do radio in Washington D.C.
The man in question was Caleb W. O'Connor (not to be confused with a big band musician/arranger, Caleb O'Connor* *this was his son). He became recognized as such in 1904, after he and a fellow student at Yale Law School published "Down the Field", one of the football team's most popular fight songs. It was in subsequent years that O'Connor became known as a composer of college songs. He published his own sentimental and popular-type of songs as well, encompassing the areas of Washington, Philadelphia and New Haven, Conn.
For a great while, I have searched for recordings of these songs. Obviously, "Down the field" was the predominant result in its' number of printed copies now acquired by colleges, and a couple recordings by later groups. Surprisingly though, recordings such as one made by Rudy Vallee in 1930 for Victor Records, was hidden amongst a sea of Internet Archive items. Unless searched for very specifically, no result. On the other hand, this was from a different generation, and finding a period-accurate recording proved most difficult. The closest match was from a Canadian archive of wax cylinder recordings, from 1909. All other songs have proven next to impossible in finding a recording, despite the likelihood of these songs being recorded by popular artists Caleb O'Connor knew in his career. These included Barry Scanlon, Irish baritone from New York, Caroline B. Nichols of Boston (Fadette Ladies' Orchestra leader), and many others. A partial list of compositions can be seen here: https://en.wikipedia.org/wiki/Draft:C.W._O%27Connor_(Composer)
In addition to composing, Caleb O'Connor became a speech expression instructor, working mostly within Washington. This became part of his radio broadcasts in the 1920s on, which is another long story. It seems he was likely the first to broadcast a radio show in that area in 1922 at the former WJH station. Later radio station associations were with WMAL and WCAP. I have asked specialists from the Library of Congress if there are recorded broadcasts from that era and later in their possession, but there was little to be found. I have also reached out to what I assume are the modern-day subsidiaries of these old stations, including WMAL, with no response. It would be very interesting to hear what Caleb's broadcasts were like. Local archived newspapers regularly promoted the broadcasts and the stations themselves in articles. So, I would be surprised if nothing exists. See link above for more context.
If anyone out there can recall seeing any record labels, something in a library/other archive, or has heard Caleb O'Connor's music, do let me know! He was active in publishing music up until the early 1950s. Additional titles are much appreciated. He may have also went by the name Donald Gordon in Philadelphia, and "Bill Brand" when he had a show called "Brand News" in Washington.