“Judging him from that night, Charley could have told Mr. Greenleaf that he was intelligent, levelheaded, scrupulously honest, and very willing to do a favor. It was a slight error.”

Tom is reflecting on their mutual friend Charley’s recommendation of Tom to Mr. Greenleaf as a possible ambassador to convince Dickie to return home. While Herbert believes that Tom is good friends with Charley and his wife, Tom hardly knows them and was recommended because he had helped Charley fix his taxes. He knows that Charley’s recommendation of him is based on just that one event, which does not truly represent his character. In fact, he is unscrupulous and ethically flexible—exactly the opposite of how he is being represented. This quote shows the reader Tom’s chameleonlike nature early on, that he can adapt to the demands of particular people and social situations purely for his own benefit. It is an early hint of his modus operandi throughout the story.

“If there was any sensation he hated, it was that of being followed, by anybody. And lately he had it all the time.”

Tom’s paranoia makes sense in light of the IRS scheme he is running. However, although he claims to hate the feeling of being followed, he continues to engage in activities that could draw the attention of the police. And when he is safe and not feeling paranoid, he is bored, which is the paradox of Tom’s life and character.