When esteemed partner Edwin Poole makes a shocking entrance at the morning meeting, Brad Chase, up from the Washington, DC office, is forced to stay in Boston longer than planned, finding himself instantly at odds with Alan Shore, both professionally and personally. Meanwhile, on a dare, Shore takes the case of an African American girl who is denied the lead role in the national tour of Annie, and Denny Crane gets caught having an affair with the wife of the firm's biggest client.
Alan Shore represents an ex-lover who was institutionalized after attempting to murder him, and the partners are concerned by Denny Crane's increasingly erratic behavior.
Denny Crane's long-lost son, Donny Crane (Freddie Prinze, Jr.) — himself an attorney — represents environmental interests against the development of a shopping mall by one of Crane, Poole & Schmidt's major clients. Meanwhile Shore, with Lori serving as second chair, tries a sexual harassment case, with his ex-lover, Christine — whom he recently helped get released from a mental institution and who, he now fears, is stalking him — serving as opposing counsel. And Sally tries her first case, defending a man who was caught stealing red-handed.
When Edwin Poole escapes from the mental hospital and wanders into a criminal courtroom, he shocks the firm by taking on the pro-bono case of a man accused of murdering a police officer. Brad Chase persuades Lori Colson to use her skills from her days as a D.A. and serve as first chair in the defense. Meanwhile, Shore is encouraged by a senior partner to use extreme measures to defend a company CEO charged with shoplifting and to keep the case from going public.
Lori and Sally take on a criminal case defending a man, Jason Binder, who is accused of killing another man at a bar with a martial arts-type punch to the throat, and whose only character witness is his mother — who doesn't make the best impression herself because of her glass eye…which tends to fall out when she gets excited. Meanwhile, Shore and Tara, the sexual tension between them growing, take the case of a hypochondriac, Bill Morgan, who is suing his doctor for malpractice; and the partners are concerned when Crane takes over one of Edwin Poole's cases, especially considering Crane is not at all prepared to try the case — which is taking place the following day — and is flat-out denied a continuance by a spiteful judge.
When mayoral candidate Jack Fleming has his bid for Boston's highest office threatened by dirty politics just days before the election, his wife, Samantha, seeks the help of longtime friend Alan Shore…whose tactics put him on a collision course with the city's new power elite. Meanwhile, Lori takes the case of a man, Richard Kirkland, whose ex-wife refuses to release their son's umbilical cord blood that was stored at the time of his birth, which may be the only hope Kirkland has to fight his cancer, and Lori is forced to tell him some very difficult news.
Lori takes the case of Michael Shea, her former informant when she was an A.D.A., who was shot while robbing a convenience store. She faces a legal and moral dilemma when she argues that the bullet not be removed - despite the fact that this could endanger his life - on the grounds that it could incriminate him. Meanwhile, Shore takes the case of Walter Mack, a man accused of being a slum lord, and is irate when the judge decides to get creative in his sentencing.
In defending a man, Gil Furnald, who was fired from his post as Santa at a local department store for being a transvestite, Shore tries his own hand at pulling a rabbit out of a hat. Meanwhile, Lori finds herself in a difficult position when her therapist, Dr. Allen Konigsberg, tells her one of his patients has threatened to kill his wife, and asks Lori for advice on whether he should warn the woman.
Crane and Shore defend a major pharmaceutical company and are conflicted over what course of action to take when startling events come to light. Meanwhile, Lori faces a moral dilemma when she discovers that Tara has taken a page out of Alan Shore's book of questionable ethics.
Brad and Lori defend a woman, Susan May, who is accused of killing her husband and his mistress when she catches them in bed. Meanwhile, at the office Christmas party, Alan Shore is introduced to Carmen Flores, a woman whose ex-husband has kidnapped her children to take them to Peru over the holiday. In coming to her aid, Shore suddenly finds himself in great peril.
Founding Crane, Poole & Schmidt partner Shirley Schmidt (Candice Bergen) returns to the firm to help bring order to the chaotic office. The firebrand Schmidt proves to be a formidable adversary to Alan Shore, and gets under the skin of Denny Crane, with whom she has a checkered history. Meanwhile, Lori represents a Sudanese native who sues the U.S. government for lack of action in the face of the horrific atrocities being committed in his country, and Alan Shore defends a man who killed his mother in a fit of rage, hitting her over the head with a skillet.
One of the members of the firm falls victim to Shirley Schmidt's mandate to clean house and is ordered to leave immediately. Meanwhile Lori, with help from Denny Crane and Shirley Schmidt, defends a school superintendent being sued by two science teachers who were fired for refusing to teach creationism. And Bernard Ferrion, Alan Shore's client who killed his mother by whacking her with a skillet, finds himself in need of legal help once again, but Shore refers the case to Tara, as he cannot hide his disappointment in his former client. And Shore is genuinely surprised when he learns his assistant, Nora Jacobs, is offended by his inappropriate advances.
Brad defends a high-profile publicist who is being accused of entering into a lesbian relationship solely for financial and personal gain, all the while hiding her true heterosexuality from her lover. Meanwhile, Shore hires Catherine Piper (Betty White) to be his new assistant, and she wastes no time offending everyone in the office. And Denny Crane, initially insisting he try the case solo but reluctantly allowing Shore to serve as second chair, defends a doctor who is being sued for prescribing a drug that has not been approved by the FDA.
Shirley Schmidt and Denny Crane represent a man whose steakhouse is being put out of business as the publicity-hungry mayor has pushed through an ordinance banning red meat for fear of Mad Cow disease, and in the process of trying the case, Crane wins over Schmidt's respect as an attorney. Meanwhile, what begins as an evening out for Alan Shore and Tara Wilson ends in a barroom brawl, with Shore arrested for conspiracy to commit assault and battery. And Lori and Brad serve as second chair for a new attorney Schmidt has just poached from another law firm who refers to himself as "Sexy Man."
Denny Crane's son, Donny (Freddie Prinze, Jr.), is the opposing counsel in Denny's trial -- an obvious attempt to settle a score with Denny for letting him believe for 25 years that he was his father. Denny tries the case with Chelina Hall (Kerry Washington), an associate at the firm. Meanwhile, Shirley Schmidt recruits an extremely reluctant Alan Shore to defend a police officer accused of torture. And Shore's former client, Bernard Ferrion, is befriended by his secretary, Catherine Piper (Betty White), much to Shore's dismay.
Multi-Emmy Award winner Carl Reiner guest-stars as Milton Bombay, a client of Schmidt and Crane, who is an old adversary and legal legend wishing to be frozen and stored in a cryonics institute. Meanwhile, Alan Shore and Chelina Hall represent a high school student who is seeking an injunction to reverse the policy of his principal, Steven Harper (Chi McBride, reprising his "Boston Public" role), who has banned a particular news network from school grounds on the basis that it is biased and incendiary.
Alan Shore travels to Texas with Chelina Hall to make a last ditch appeal for death row inmate Zeke Borns, a man with diminished mental capacity who was convicted of a crime he does not even remember committing. Meanwhile, Denny Crane and Shirley Schmidt defend Miriam Watson (guest star Shelley Long), a prim and proper businesswoman who is charged with engaging in sexual conduct for a fee, and Lori Colson, fed up with Denny's offensive behavior, approaches Schmidt and Lewiston to lodge an official complaint.