John alongside Eva investigates the case of homeless man who died of overdose. The best friend of the homeless man believes it was a homicide. While searching the belongings of the dead homeless man, John gets hold of an expensive guitar in his locker. In the meanwhile, John remembers when he was an addict and entered a 12-step program in 1964 after being drunk too many times.

John and Eva investigate the murder of bullet-ridden body found in Chinatown. However, the body looks similar to Amsterdam's lost son from the 1900s, Roosevelt.

Andy Gleason, John's first partner on the force, is dying of leukemia brought on by a bullet wound fired by an unseen shooter. He asks John to bring his killer to justice due to his weakened condition. The investigation brings John into contact with the Russian Mafia while he flashes back to how he got started as a police detective.

Eva investigates the case of a woman who apparently drowned, alongside John who is recovering from a gunshot wound. The death is apparently related to robberies of wealthy men linked to a dating service. In the meanwhile, John looks back at his life in the 1920s, when he committed fraud and stole an expensive diamond pendant from his lover. Also, John wants to be sure if Sara is his true love, who can convert him to a mortal. But John is unwilling to hurt her feelings by keeping secrets about his past to himself, and as a result, decides to back away from the growing relationship between the two.