The second installment of this saga of gangland lore follows gregarious gangster, Michael Hardy, further down his twisted criminal path. The Last Jewish Gangster, The Middle Years, starts in 1968 with Hardy sentenced to twelve years in the world's most dangerous prison in Mexico after taking the rap for his mother's counterfeiting scheme, hoping to have finally earned her love and respect.

Once he's released from prison, Hardy returns to Brooklyn and tries to go straight, but drifts back into a world of crime. He gets Sammy "the Bull" Gravano to join his crew to pull major heists like kidnapping drug lords for million-dollar ransoms, and robbing cop bag men. To evade the law, he goes to Europe and ends up in Israel where he works on a Kibbutz, touching the hem of his Jewish heritage.

Hardy devolves further into a gangster's life when he returns to Brooklyn, running a finger of the Mob's Five-Fingers International Car Theft Ring, participating in a stolen airline ticket scam, and doing fourteen hits for the Mob, still hoping his mother will take notice. When she gets busted for the car theft ring, she turns him in to reduce her time.

Crushed by his mother's callous self-interest, Hardy ends up cutting a deal with Rudy Giuliani to nab a dirty cop to reduce his time and negotiate his place in the witness protection program. Relocating to LA under an alias, it doesn't take long for Hardy to land a gig as muscle for a Hollywood studio and meet his future wife, a sex worker who stole from his mother. The lines between love and revenge begin to blur.