The protagonist of Miller’s Crossing, Tom, harkons back to Hammet’s Ned Beaumont, the cynical idealist that keeps his friends close and his enemies closer.
It would appear that just as much as his gambling habits, Tom’s hat is an equally important element of his identity. And though he says that a man chasing his hat is foolish, he is constantly chasing something, if not an identity. Like most gangster flicks, Tom lives in a world where nothing is certain and change could come at the drop of a hat (or a gust of wind). Friendship, character, and hell, I ain’t afraid to say it; ethics are constantly in jeopardy, and Tom continually has to makes choices of whether of not to chase them, or let them blow away.
Appearing to be emotionally detached from just about everything, I think he does care. Even in his line of work, he cares about honor, ethics, love, friendship. But just as we only see Ned Beaumont from the surface, we can only speculate as to what’s going on behind Tom’s sunken eyes.