Since the departure of Michael Kuzak, Victor Sifuentes, Abby Perkins, and Jack Sollers from the firm, McKenzie and Brackman are looking for more litigator power. Grace, having suffered from a miscarriage and leaving Victor, returns to the firm and is immediately given a high-profile case with Mullaney in defending Elsa Chandler, a woman charged with murdering her abusive husband. McKenzie tries to adjust himself to the brash new tenant sharing office space, the crude, smart-mouthed, chain-smoking, entertainment lawyer Susan Bloom, to boost revenues for the sagging firm. Meanwhile, Becker's secretary, Gwen Taylor, is on jury duty and witnesses Bloom's associate, the crafty Frank Kittredge, go to the limits of ethics to defend his wealthy client from an assault charge. Kelsey and Markowitz struggle to find the right nanny for their son, Matthew, and they hire Ned Barron, a college student just right for the job. Also, Billy Castroverti is hired as a new junior associate.

The firm worries about its reputation when Kittredge takes a high-profile criminal case of defending a mobster leader for allegedly murdering a rival mob leader and the new D.A., Ruby Thomas, becomes determined to see the case won at any cost. Meanwhile, Markowitz takes a rare court deposition in representing two women basketball players suing the Hollywood Hoopsters for wrongful termination.

C.J. takes a close interest in Becker's case involving a custody suit of her former lover, Maggie Barnes, whose past lesbian love affair with C.J. has threatened to take Maggie's children away and put them in the care of her ex-husband. Billy Castroverti is fired for his unsatisfying work performance. Low staff morale makes it difficult for Brackman to organize the annual Christmas party, so Benny and Castroverti take over the chores and intend to go all out. Meanwhile, Kelsey fumes as Markowitz is forced to go out of town to miss their son's 2nd birthday party. Zoey and Rollins quarrel over their plans for the holidays. A holiday card from the late Rosalind Shays brings a form of relief for both McKenzie and Grace. Also, a mentally unbalanced temp office worker, named Betty, drives everyone to distraction.

Mullaney aids fellow lawyer, Alex DePalma, in a class action suit by Honduran banana farmers suing an American chemical company who claim that a company-designed pesticide made them sterile. Meanwhile, Margaret Flanagan (The district attorney who unsuccessfully prosecuted Earl Williams for the murder of Nina Corry in Season 4) confides in Zoey about her troubled past as she begins to confront long-repressed memories of child abuse. Kelsey goes out on a dinner date with Matthew's nanny, Ned, while Markowitz meets a regal actress he admired as a child.

Becker tries to win back Roxanne after his psychologist suddenly dies during a session. Meanwhile, Brackman and his ex-wife, Sheila, clash again when their youngest son, Alexander, gets in trouble with the law. Susan Bloom shocks the office with invitations to her unexpected wedding to Mikhail, a Russian movie actor. The Markowitzes' nanny, Ned Barron, went too far when he comes on to Ann Kelsey again and he is fired. DePalma asks McKenzie for help when his participation in the judicial sting operation impairs his ability to function in court when faces the wrath of other judges in his quest to find one for his latest case involving defending an alleged embezzler. Ann Kelsey was arrested for obstruction of justice and suspicion of illegal aliens by INS Agents when she bought a new nanny and having her son Matthew returned home. Also, Gwen and Kittredge's romantic fling quickly turns into a torrid affair.