The Story of the Man with the Watches was published by The Strand Magazine in 1898, during The Great Haitus. This and 11 others were published as part of the "Round the Fire" series. It was later published by John Murray in Tales of Terror and Mystery (1922). This is not a Sherlock Holmes story.
I should clarify that the world's first consulting detective is not named, but definitely-perhaps seems to make a "well-known criminal investigator" appearance. Although to call it an unnamed cameo would be a tick much. The same can be true in the later in the same year and series "The Story of the Lost Special." But does Holmes appear? Are these two non-canonical Holmes stories or Doyle playing around in the genre sans an overshadowing detective of his own creation? Are they extra-canonical? Apocrypha? Typically the latter.
It bears mentioning too, that this occurred one-year after ACD had his new Undershaw Estate built in Surrey. A thing which went apparently quite over-budget. So that factoring in this real-world understanding--perhaps this Holmes/not Holmes devise is him having his cake (keeping Holmes shelved) and eating it too (cashing in on some level of hungry readership familiarity). Also, The Strand was still I'd imagine reeling off the reported 20,000 subscription cancelations they suffered on the heels of Holmes' death/eventual hiatus.
It's not that Doyle hated Holmes, he just viewed him as an impediment to overcome on his way to more serious authorial endeavors. He, therefore, threw him off the Reichenbach Falls, arm-in-arm, collar and elbow lock-up with a hastily-created Professor Moriarty (The Final Problem, 1893). Fin. Except, of course not really because then came Holmes' return to life from the never-was dead in The Adventure of the Empty House (1903). Due to popular demand, the Persian slipper was at long-last refilled with shag and the coal-scuttle with cigars, and the game was again afoot. Hiatus: over.
An interesting thing about The Hound of the Baskervilles (serialized 1901-02 in The Strand) is that it could easily yet brilliantly-so be read as a spooky tale with Holmes merely plugged into it. Also, to be clear, Holmes was not back from the not-dead within its pages, as HOUN is stated to have happened quite earlier than FINA.
Nevertheless, he does appear as somewhat of a ghostly apparition therein. Perhaps he haunts ACD in The Man with the Watches in a still more subtle fashion, a few years prior. A slow crawl back up to the land of the fully fictional living. Doyle's good friend JM Barrie seems to have thought he might be reborn all along*and after all. If it is, in fact, Holmes, he is a bit shall we say (and as we shall see) rusty under his Sigerson AKA? But this yarn. Let's un-ball it and see what's what.
What's what is homosexuality and gender-bending. Also card-sharping, a black sheep, and keeping mom in the dark as to much of it. Throw in a dead father and a son trying to fill that void. All that, and within whodunit's natural habitat, a train car. This is a fun, quick, and somewhat thought-provoking story; and also one maybe a bit ahead of its late Victorian Era time for the handling of aforementioned what-whats.
That said, it's also quite of its time, in the English eyeing with a side-long glance, the ready and wanton violence and corruption of the Wild West and Tammany Hall happenings across the pond. More to the point, its criminals threatening to bring their criminal behaviors to Joly Old (a recurring theme within Doyle's writings). Here, we are introduced to such a criminal, Sparrow MacCoy, a New Yorker "at the head of his profession as a bunco-steerer. green goodsman, and general rascal."
[A brief interjection. A green goods scam involved conning marks into paying good money for funny money.]
It was there that Edward, the younger brother of James by ten years, first partnered with MacCoy. Professionally and perhaps, we'll say, personally. Upon the death of their father, James took on somewhat of a paternal role in Edward's life. The family moved from England to America in the 1850s, and young Edward who was never a great egg became a downright bad one. "... at the end of a year or two, he was one of the most notorious young crooks in the [New York] City."
And now he's dead. Shot through the heart and who's to blame? "... neither the guard [John Palmer] nor the experienced detective officers could suggest." He was mysteriously in possession of six American pocket watches on a train in England. While dressed in his familiar guise of drag and accompanied by MacCoy. Another person was there, "a small man with a cigar in his mouth." They were moved away from the smoker. The other fellow had vanished, leaving only a half-smoked stogie. In fact the lady is gone too. Where is MacCoy come to think of it? Everyone is stumped.
Except for "There was a letter in the Daily Gazette, over the signature of a well-known criminal investigator..." Brother James addresses this letter via response to tell his tale. You see Mr. Well-known's deducing "... it was wrong, it was a mighty ingenious one all the same." But the truth must be told. In a way, then, our maybe-Holmes at least led to it coming out. Flushed it out, like so many a hound.
MacCoy, an older man "between fifty and sixty years of age," and "The two might very well have passed as father and daughter." I've quoted enough at this point, I'll stop now. I believe proof positive has been furnished that I, in fact, read this thing. You see, the cigar guy was James, the older gentleman obviously MacCoy, and the dead man the life-long beautiful boy then switched into boy's clothes, Edward. Long story short, McCoy accidentally shot Edward in an intervention gone tragically awry.
It is James who narrates this whole shebang, and whether he knows it or not, the whole shebang is a love story maybe even more-so than a murder mystery. His brotherly love for Edward, paired with a tinge of the fatherly varietal. The love of MacCoy for Edward, albeit platonic or otherwise (I'll shy away from fatherly), and even the bleeding-over for the older crook onto James, as he couldn't leave his blood on his hands especially after Edward's. So, in a manner of speaking, this The Man with the Watches is a love triangle.
James wanting what's best for Edward in his eyes, and MacCoy wanting much the same. With I'm certain Edward being torn twixt the pair. But more than that, between Sunday School and what he saw as his own true self. I hope big brother got his family Testament back. I also hope that Mom somehow knew of her boy's fate. She reads as maybe having a great deal of an inkling up until the bitter end. The most tragic part of this read is the thought of being a parent and not knowing. Not being cued-in, in the end-all. That's the part that'll stick with me.
I said I wouldn't but "His name was the last on her lips." Her baby boy, in her mind, making an honest London living.
::: very :::
ADDITIONAL READING: "Elementary, My Dear Watson" (Some Thoughts as to Sherlock Holmes Canon) (Search Kaplowitz Media. on the right-side of your screen.)
Online resources for this article include: Lit2Go, Doings of Doyle, Wikipedia (Sherlock Holmes (The Great Hiatus), Canon of Sherlock Holmes, Undershaw, Green goods scam), and The Arthur Conan Doyle Encyclopedia.