The media harasses Judge Joe Rifkind and a higher judge for the shooting of a rookie police officer who was killed by a young criminal the judge set free. To make amends, Judge Rifkind pays a visit to the father of the rookie police officer who also happens to be one of his former police partners. Assistant DA Bobby Esposito's brother, Frank, is given another chance to stop using drugs, but when he doesn't show up for his flight to the rehabilitation centre, Bobby assumes he's been deceived by Frank again. Meanwhile, Bobby and Cynthia Bennington's relationship heats up despite the one secret Bobby can't bring himself to tell her.

Judge Joe Rifkind, a liberal judge whose nickname is ""Let-Em-Go-Joe,"" releases a petty offender who jumped a subway turnstile. The decision starts a chain of events that end a rookie cop's life, and possibly the judge's career. Standing by Rifkind are his wife, Sarah, and his friend and colleague, Judge Attallah Sims. Sims has a firmer view of justice than Rifkind; her nickname is ""Attallah-the-Hun."" Meanwhile, Assistant District Attorneys Bobby Esposito and Cynthia Bennington are getting to know each other. Cynthia is uptown money. Bobby's Brooklyn, working class roots could demolish his success when his father asks him to erase one of his brother's drug convictions to save him from life in prison.

When the mayor's lead in the upcoming primary begins to wane, the press sites Judge Rifkind's ordeal as one of the Mayor's problems. The mayor puts in motion a plan to have Rifkind removed from the bench. In the ADA's office, maintenance removes Bobby's computer so it can be evaluated for misconduct and Cynthia is called into District Attorney Spiegelman's office. Spiegelman wants her to testify against Judge Rifkind for sexual harassment. He claims someone witnessed a harassing remark Rifkind made to her. She denies anything ever happened but is forced to reconsider when threatened that her testimony will keep Bobby out of jail. Meanwhile, Judge Attallah Sims has her own plan for helping Rifkind.

In the season finale of 100 Centre Street, justice takes a side step when a popular football player is brought into night court for beating up a female groupie. Cynthia attempts to prosecute, but the victim is unwilling to talk and the presiding judge is a fan of the player.

Television executives offer Judge Sims her own show. Cynthia and Bobby contemplate opening a legal aid office for people who don't have money for representation; Bobby would investigate and Cynthia would defend.

Penelope returns to Judge Sims and Rifkind makes his decision about whether he should teach law or stay on the bench.

An ambitious new Assistant D.A., Jeremiah ""J.J."" Jellinek, arrives at 100 Centre St. and immediately starts jockeying for a position on a new task force, run by acting D.A. Gil Byrnes, that is going after the construction industry for its ties to the mob. Cynthia and Bobby set up their non-profit legal aid business, People's Defence, in Washington Heights and land their first client, Rudolfo, a 17-year-old accused of brutally beating a teacher. Judge Attalah Sims' last case of the night is a catatonic young woman who goes by the name Rebecca Rifkind, who turns out to have some connection to Judge Rifkind's past.

Judge Rifkind becomes reacquainted with his daughter, Rebecca, who harbours animosity towards him and her stepmother, Sarah. J.J., the new assistant district attorney, continues to forge new ground in night court and sparks a smouldering relationship with Fatima Kelly. Bobby and Cynthia's case becomes increasingly difficult when the mother and sister of their 17-year-old client, Rudolfo, offer opposing views on his integrity. Bobby also gets different opinions on Rudolfo from a jaded high school principal and the teen's employer.

A reluctant and still angry Rebecca is forced to live at home with Judge Rifkind and his wife, Sarah. Ramon suspects Fatima of using drugs, but his attempt at a drug intervention goes awry. J.J. goes undercover and visits a lawyer for a construction company suspected of having ties to the mob. Cynthia's father is concerned for her welfare, and Judge Rifkind convinces him to watch her in court to see for himself how much she loves what she does.

Sarah and Rebecca come to blows at home and Sarah reveals that Judge Rifkind may have prostate cancer. Mary Ryder continues to push for overturning her husband's murder conviction. Cynthia and Bobby suspect foul play in the Ryder case. Judge Rifkind discovers a former cabaret singer, Lee Ann Halsey, drinking at a jazz club where Rebecca's boyfriend, Rush, tends bar and plays guitar. Rifkind convinces Halsey to try singing again. Bobby approaches Willard Block, the man who got him kicked out of Centre Street, for advice on the Ryder case.

Ramon gets his big break when a notorious environmental activist, on trial for blowing up a water tower as part of a protest, asks him to take his case. Unfortunately, a renowned environmental lawyer swoops in and steals the case from Ramon. Rifkind agrees to visit Lou, a Buddhist monk that Rebecca has been seeing. At the last minute, the environmental lawyer convinces the activist to plead guilty, just as Ramon predicted. Rebecca's boyfriend, Rush, steals a valuable Buddha from Lou to buy drugs and Rebecca turns to her father for help. LeeAnn's comeback fizzles as she refuses to take the stage.

Ramon defends a teenager accused of horrible gay bashing. The teen insists he's innocent. Ramon tries to cop a deal with the Assistant D.A. for a lesser charge only to discover that he may have been manipulated. Rebecca moves out of the Rifkind home to take a job at a health spa in Baja. Bobby decides to quit his job as an investigator, which may end his relationship with Cynthia. Acting D.A. Byrnes takes J.J. under his wing and offers to be his mentor. Desperate to score more drugs, Fatima breaks down in Michelle Grande's office. Ramon's wife goes into labour and while in the waiting room meets a gay man whose lover is dying.