Whistling Dick’s Christmas Stocking by O. Henry ★★★☆☆ #BookReview #BookBlog #ShortStory


Primary Genre(s): Fiction, Classics, Short Story
Published:  December 1899 issue of McClure’s Magazine
Page count: varies depending on source; @30
My Format: Audiobook via Hoopla; free online
Pacing: Good
Ending: Unexpected
Would I recommend it: Probably

My rating: ★★★☆☆

It’s about a railway tramp traveling in the South who retrieves a lost gift off the back of a passing surrey. On Christmas Eve “the skirts of Fortune had swept him into their folds.”

My Thoughts
After reviewing The Gift of the Magi yesterday, I continued to look for more O. Henry short stories. I found another Christmas-related story, albeit loosely, to review today. There are several free online copies available if you are interested in reading this yourself. Here are my pros and cons for Whistling Dick’s Christmas Stocking:


  1. First off, a bit of trivia… this was the first story that William Syndey Porter used the pen name O. Henry.
  2. This story felt authentic to me, all the way down to the vernacular it was written in. Honestly though, I am not sure I would have followed the story quite as well if I was reading it versus listening to the audio version. The audiobook make the colloquial speech and the accents come to life.
  3. Whistling Dick is a hobo with a heart of gold. He stands out among his peers because he isn’t jealous of others’ prosperity, particularly compared to his, and he certainly doesn’t believe in taking what doesn’t belong to him. Even when circumstances occur that could change his entire lot in life, he still chooses to keep living the current life he is living and he is content.


  1. While this story takes place between Christmas Eve and Christmas morning, I wouldn’t necessarily characterize it as a Christmas story per se.
  2. Who am I to second guess someone like O. Henry, but I wish he would have had Whistling Dick ask the Planter to transfer some of the goodwill he earned to the other workers rather than just let it go. Since Whistling Dick didn’t want the reward for himself, it would have been another kindness to pass it on to others.

Whistling Dick did a kind deed and “the skirts of Fortune had swept him into their folds.” However, he didn’t accept the “Fortune”. The fact that he didn’t accept the rewards for his actions is at least a little odd to me. I’m not sure if the message was to be content with what you have or to just be honest and kind and not expect rewards for good deeds.

Being content with what you have is a good message, however, if/when a genuine and legitimate opportunity presents itself to improve your circumstances I would imagine most people would do it. Personally, I am of the mindset that when my circumstances improve, then I can do more to help others with their situations. While I understand the romantic appeal of total freedom, I also can’t imagine the anxiety over where the next meal will come from or any number of other misfortunes that befall homeless people. I guess as long as Whistling Dick wasn’t causing any problems and taking care of himself, then it was his right to accept the new circumstances or not.

Perhaps, though, the moral was simply to be honest and kind and not expect rewards for doing the right thing. Again, this is a great message and one we should all embrace throughout the year, not just at Christmas!

Regardless, I didn’t enjoy this story as much as The Gift of the Magi. It was good, but not great.


Click here for a description of my rating scale.

(The image above is from the Kindle version of the story published 9 October 2012 by Acheron Press.)

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