Jake finds himself in an unusual situation when two past clients return at the same time. A call from the Innocent Inmate Program causes Jake to worry that he is being targeted for having sent an innocent man to prison twenty-one ago. After learning he is not a target Jake decides to join the Innocent Inmate Program team in a challenging legal battle to free his former client. He quickly realizes that re-investigating a crime that happened nearly a quarter of a century earlier involving a Chinatown drug gang is even more difficult than it sounds. Then there is Penny, who Jake represented four year earlier on a minor drug charge. Back then Penny was an innocent kid, a runaway from an affluent family. But this time around Penny is a full-blown addict facing a felony drug charge that could put her behind bars for thirty or more years. Recalling what Penny was like when he first met her, Jake wants desperately to save her. When Penny reveals she has evidence that could result in a dismissal of the charges Jake questions if that is in her best interest. Faced with an ethical dilemma Jake follows his conscience and finds himself on a path that could lead to personal disaster. Set as always in New York City, Second Time Around features the usual cast of Broken Lawyer characters.