Thank you both very much for your replies.
Bob’s closest match is (on Ancestry)
545 cM, across 15 segments, longest segment 82 cM. The next closest is
415 cM, across 15 segments, longest segment 86 cM.
Bob’s grandmother lived in the same city as some of the “Murphy” male and female siblings. The Murphy brothers, who were single at the time, may have lived in the same neighbourhood as Bob’s single grandmother (I have to check). Not that it matters here, but I reviewed my notes and this happened during the 1910s, not the 1920s.
Bob is an only child. His mother was an only child. Bob’s mother passed before DNA testing became widely available. We most likely would never contact the Murphy descendants as Bob isn’t terribly interested in genealogy and it probably would cause more harm than good.
Due to how complete one online tree is, I believe I know who the grandfather was but as mentioned, there are two men I’ve never been able to trace. Yes, it’s time for more detective work (to satisfy my own curiosity).

Thank you again.
[If it wasn’t for their online photos, I wouldn’t be as curious. One descendant, who passed on fairly young, looked like Bob when Bob was young.]