Harry runs the joint. He provides the booze and the rooms, so the others need to keep on good terms with him. Harry likes the power, because it reminds him of the old days when he had big political connections and held some sway in the neighborhood.
More than power, though, Harry wants to be liked, and that’s why watching him work is like watching a man play tennis against himself. He plays both sides of the net. He’ll yell at Rocky to make one of the “bums” quiet down, and then he’ll yell at Rocky for being mean to the guy:
What the hell you doing to him, Rocky? I didn’t tell you to beat up the poor guy. (1)
The idea of the pipe dream comes up with everyone in the bar, but it burns brightest in two of the characters. Hope is one of them (Jimmy is the other). There’s no subtlety in his name (he’s even listed as “Hope” in the dialogue). He hasn’t left his own establishment in twenty years.
Think about that for a second. This is a guy who has decided that he’s good with hanging inside for two straight decades. Now, Harry keeps saying he’s going to take a walk real soon, and for a minute O’Neill manages to convince us that there is actually hope for everyone in the bar when Harry finally takes his trip outside.
Of course, there is no hope for Harry. His name’s a cruel joke. He can’t move forward, because he fears change. He sees change attempting to creep into his life at every turn—in the form of these newfangled automobiles for instance—and all he can do is hole himself up in his alcohol-drenched cocoon and hope he’s safe from all that scariness.
The phantom car that he says nearly kills him is just one in a long line of illusions Harry has created for himself. And we’re not talking cool levitation illusions either. We’re talking about a series of indestructible lies the guy tells himself. He’s even crafted an elaborate story about how his love for his dead wife has kept him inside all these years, but it turns out he never even really liked her that much. Harry has resigned himself to this life, and the outside world holds nothing but terror and despair for him.Harry Hope's Timeline