Which Men Might have Beaten Sherlock Holmes Early in his Career?

I figured it was about time I posted another article here.  First, to celebrate the first year of the blog, and, second, to honour Sherlock Holmes’ 159th birthday.

In the short story, ‘The Five Orange Pips,’ Holmes indicates, “I have been beaten four times – three times by men and once by a woman,” but we are only explicitly told the identity of the woman, Irene Adler.  Who might the three men be?  Several hints to the possible identity of one of these are given in ‘The Red-Headed League.’

In referring to this person, Holmes discloses, “He is, in my judgment, the fourth smartest man in London, and for daring I am not sure that he has not a claim to be third.  I have known something of him before.”  Later in the story Holmes says, “I’ve had one or two little turns also with [him], and I agree with you that he is at the head of his profession.”  Next, Holmes remarked that he had an ingenious mind.  Also, he declared that this person was “one of the coolest and most daring criminals in London.”  Based upon these statements, this mystery man may have been one of the group of three alluded to earlier in this post.  I refer, of course, to Mr. John Clay aka Vincent Spaulding, Jabez Wilson’s able assistant at his pawnbroker shop.

Any guesses on the other two anyone?  Keep in mind these cases must have taken place before ‘The Five Orange Pips’ unless Watson once again fell into the old habit of telling his stories wrong end foremost.

Thank you all for reading this.  Happy birthday, Sherlock Holmes!


49 responses to “Which Men Might have Beaten Sherlock Holmes Early in his Career?

  1. A motivating discussion is definitely worth comment. I think that you ought to publish more about this issue, it might not be a taboo matter but usually folks don’t talk about such topics. To the next! Best wishes.

  2. So, no one has taken up your challenge??? I am re-reading Doyle’s Holmes and I will try to come up with a response as to the other two men who have ‘beaten’ Holmes… great poser. I am new to your blog. I am intrigued and delighted. While I’ve been a fan of ACD for years and years, I’ve never been part of any group to discuss such fine points. What a delight the internet is! Thanks and watch for my estimation (I never guess).

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  12. Well Happy New Year to you, and Thank You for sending out this post!

    Your e-post made it to me while I was listening to Elsie Cubitt (The Dancing Men) … some years ago my wife got me the CD,


    I have really appreciated the quality of the music, and can almost see the capers unfold as the music is played.

    Now back to your question … I’m not really sure, but will have to give it additional thought.

    Best Regards!



    • The music you linked to is great!

      Perhaps a younger Professor James Moriarty or the London accomplice of Jefferson Hope who impersonated a woman and came for the advertised ring in ‘A Study in Scarlet’ would be good candidates for the other two men who beat Holmes though I would think they are both somewhat of a stretch.