Koenig investigates negative rumors about Syed, though the rumors do not directly connect him to Lee's murder, and the most troubling rumors cannot be substantiated. People from his mosque were scared when he was arrested, some describing his story as a cautionary tale. Some believe Syed was duplicitous, capable of committing the crime. One rumor, that he stole money from the mosque, was partially confirmed by four people. Syed admitted taking some money when he was in eighth grade, but his mother found out, and he felt ashamed. Syed had a reputation as a peacemaker, "a good guy", helpful and caring. People who knew him in high school cannot believe he planned Lee's murder. Did Syed "lose it", and nurse feelings of rejection? Could Syed have committed murder in a dissociative state, not knowing he did it? Koenig explores whether Syed has true empathy or anti-social characteristics, and consults with psychologist Charles Ewing, who has interviewed many young murderers. Why does Syed not sound more angry about Jay or other people connected to his case? In an 18-page letter to Koenig, Syed reveals his concern about being perceived as manipulative, and says it doesn't matter how the podcast portrays him.
