Gortsby is one of life's observers. He likes nothing better than to engage in a spot or two of people-watching. From his exalted position on a park bench, he enjoys casting his Olympian gaze over the great mass of humanity that passes by. He's especially keen to observe life's losers, who tend to congregate in the park as the dusk falls, after all the successful, well-to-do people have gone home.
Gortsby's wide experience in observing other people has made him rather cynical and detached. When the young man sits next to him and starts spinning his shaggy dog story about why he needs to borrow some money, Gortsby immediately senses he's being conned. At the same time, Gortsby's cynicism isn't such as to make him cold and unfeeling. Once it becomes clear that the young man's telling the truth after all—or so Gortsby thinks—he doesn't hesitate to help him out. In fact, he actually goes so far as to run after him to give him the money he asked for.
But Gortsby's rather smug sense of superiority to life's defeated gets its comeuppance. His fascination with people he regards as losers has led him to be drawn into their world. Outside of his normally detached comfort zone, Gortsby has himself lost out. Thanks to the clever young con artist, Gortsby has now become a loser, momentarily joining the massed ranks of the defeated.