There are a few things that strike me about this story, but I’m going to talk about just two.
First, the punny title. Yes, there’s a race. But isn’t Joyce also commenting on the Irish people and how they always seem to come in last?
Second, money, money, money… and all that comes from having, or more importantly not having, it. The myopia when it comes to your own potential. The constant tension of possible humiliation in the simplest transactions. The envy. The risks that come with the simplest activities that no one else sees.
I’m reminded of the scene in the generally horrible movie The Pursuit of Happyness when the rich CEO, in a hurry and without any cash on his person, asks the main character to borrow $5. To the CEO it’s a simple courtesy. To the person he’s borrowing from it’s his last $5. And more than that, the lender giving up the $5 knows it’s such a trivial sum to the CEO that he’ll likely never think to actually pay it back. So not only does he lose the $5 he desperately needs, but faces the humiliation of having to ask for repayment.
I’m reminded of an editorial I once read (I’m composing this offline so can’t find a link, but Google should reveal all) that was composed entirely in the form of a litany in the form of “being poor is” statements. Things like:
Being poor is hoping your toothache just goes away
Being poor is making excuses to go to the bathroom so your friends won’t hear you ask for the free lunch… or might not notice you aren’t eating at all
Being poor is being angry at your kids when they ask for all the things they see on TV
Being poor is having sheets for curtains
I can add one: being poor is feeling that moment of panic every time you go to the parking lot and for a moment don’t remember where you parked your car… because you know what it’s like to have your car repossessed and even many years later and for no rational reason you fear it’s happened again every single time.
The strain of living with the fear and constantly wearing a disguise lights a fire in some people, spurring them to greater achievement (the romantic and cinematic view), but it breaks most.
This is Jimmy’s existence. Living a life of pretense. Literally gambling away everything he had saved to make even a feeble attempt to break through the barriers of class and poverty… to the very group he wants so desperately to be part of.
At the end of the story: daybreak! But one whose light will reveal, once again and harshly, very different lives for the (foreign) well-to-do and poor, Irish Jimmy.

Nice catch: again our tastes align. This is one of my favorite stories in “Dubliners” so far, and I intended to write something about it on my blog. At least here I can take a minute to note that “After the Race” reminded me of Hemingway, all the way down to the seemingly antithetical ending (which, in particular, evoked the insistently renewing/reminding morning in “The Sun Also Rises”).