> The only reason it goes to one and not the other is something random like the order the routes are defined in the file?

To be fair, that's not random, that's pretty explicit. And if you're optimizing for speed, short circuiting at the first match is a good idea.

But if you're using a router, chances are you're passing the segments as arguments to some function or method anyway, so route /a/*/c and /a/b/c should both wind up returning the same content if the second segment in both cases is 'b'.