New York attorney Carl Sack joins the Boston branch of Crane, Poole & Schmidt, ruffling feathers amongst the staff, including Denny who is arrested for soliciting a prostitute, and Clarence who is targeted for performing in a drag show. Meanwhile, Alan defends Shirley when she is sued for withdrawing a large contribution to an academic study, but is distracted by the familiar opposing council. Jerry helps freshman lawyer Katie Lloyd try her first case involving a murder suspect who refuses to cooperate.

Alan has his hands full trying to keep Denny away from Lorraine when she is hired by Shirley as a new associate at the firm. At the same time, he and Jerry try to mold Katie into a full-fledged lawyer by preparing her for her first murder trial, but things go awry when she makes a spur-of-the-moment decision in open court. Meanwhile, Judge Weldon's request to have a baby makes Alan question his potential for fatherhood.

Alan represents a teenage girl who blames her high school's stand on contraceptives for her contracting AIDS, while trying to work alongside Lorraine without distraction. Meanwhile, Jerry and Katie take on the case of a woman suing her husband's psychologist for causing his death, and Shirley is furious when Denny and Carl bet a huge sum of money on the outcome of a case involving cockfighting.

Shirley is compelled to help an old friend of Denny who is discharged from the army for coming out publicly as being gay, but finds resistance from the judge for challenging America during war time. Meanwhile, Alan's "word salad" returns whenever Lorraine is around, and new associate Whitney Rome is thrown into a case involving a bullfighting child whose mother wants sole custody.

Alan is shocked when a woman asks him to represent her for a murder she has yet to commit on the basis of "temporary insanity" and turns to Denny for help. Meanwhile, Katie and Jerry once again represent Joseph Washington who is being persecuted in his home town for a crime he did not commit.

Denny angers the senior partners when he fires an associate for being fat, consequently bringing a large lawsuit against the firm. Alan enlists the help of Whitney in the case of Patrice Kelly whose temporary insanity plea is not going over well with the jury in her murder trial. Meanwhile, Jerry helps a client who shares his affliction of Asperger's syndrome and begins to show some affection.

Whitney and Katie defend an ex-cop charged with murder, but are shocked to find that the main piece of evidence is an MRI of his brain that "proves" he is a racist. Alan defends Denny in court when he is charged with wrongful termination after firing an associate for being too fat. Meanwhile, Carl is furious when once again Clarence is caught on YouTube in drag, and Jerry is nervous about taking his new relationship with Leigh to the next level.

Denny is once again arrested, this time for allegedly soliciting gay sex in the court men's room, and again turns to Alan for representation. Shirley is surprised to find Bethany as her opposition in court when she defends an old "shock-jock" friend for saying offensive things over-the-air. Meanwhile, Katie begins snooping around when she suspects Lorraine is not who she says she is.

Alan takes on one of his most outrageous lawsuits to date when he teams up with Denny to sue the National Guard for failing to show up when a flood wiped out a small business. Shirley is surprised when her granddaughter visits her at the office with the news that she was expelled from university for destroying government standards tests. Meanwhile, Carl has second thoughts about staying in Boston, and Lorraine comes clean to the firm about her true background.

The firm stands to lose millions of dollars when GreenPeople threatens to sue for all the money they ever spent at Crane, Poole & Schmidt, alleging Denny misrepresented the firm as being environmentally friendly. Alan helps Clarence take on the bank that foreclosed on his house after he made a bad deal. Meanwhile, Tara helps Jerry overcome the grief of his breakup with Leigh, and Carl makes a decision regarding Lorraine's employment status.

Denny puts the whole firm on edge when he unilaterally takes on a high-profile murder case and refuses help from anybody else, especially Alan. Meanwhile, Jerry and Katie represent a woman whose husband divorced her after being "brainwashed" by an ad campaign from a sleazy lawyer.

Alan takes on one of his most controversial cases to date when he represents a man suing Missy Tiggs for stealing his sperm and impregnating herself to have a black baby. Meanwhile, Jerry has mixed feelings when Leigh asks him to help her get her job back after she's fired for hugging a student.

Shirley is torn when her law school sweetheart comes back into her life as opposing council, bringing back old feelings and alienating Carl. Meanwhile, Alan and Denny flirt with the idea of swinging when they both have anonymous sexual encounters in the office, and Katie is threatened by Leigh who is jealous of her relationship with Jerry.

Carl Sack represents the sexually adventurous Andrea when she sues a company for losing her mother's ashes and giving her a cubic zirconium.

Denny, tries another stunt to win over Shirley's affections. Alan and Jerry go against Melvin Palmer again when they represent Mr.Beckham, a man who's daughter was murdered after a talk show stunt and he wants to sue the production company. Shirley begins to suspect her friend, Ethan, is unstable when she learns he's been arrested ten times for shooting seals in Boston Harbor.

After her father -- who is in the late stages of a debilitating fight with Alzheimer's -- injures himself and lands in the hospital, Shirley Schmidt wants to end his suffering and asks Alan Shore to argue in court on her behalf. Meanwhile Jerry Espenson's beautiful, new girlfriend sues him for sexual assault, and Carl Sack represents the island of Nantucket whose residents want to build a nuclear bomb in case of attack.

Alan Shore gets the dream of a lifetime for an attorney when he is asked to present an appeal to the Supreme Court in the case of a mentally challenged man who has been sentenced to death for the rape of a young girl. Meanwhile, Katie Lloyd learns some startling news from Lorraine Weller about Jerry Espenson's new girlfriend.

Denny falls for a female cattle rancher who is pushing for the government to stop selling meat which has been cloned. Meanwhile, Shirley demands that Alan sues the Democratic Party after her nephew, a delegate, disagrees with his state's primary vote.

A group of high ranking politicos ask Denny Crane to run for President of the United States. Jerry Espenson's ex-girlfriend, Dana, asks that he defend her after she's arrested for prostitution. Carl Sack and Shirley Schmidt represent a woman who is suing the Archdiocese for not permitting her to become a priest.

Patriotism is in the air as Alan and Denny celebrate their acceptance into the Auxiliary Coast Guard. But when the town of Concord, Massachusetts decides to secede from the United States, Alan accepts the case, and deeply offends Denny. The case takes a personal turn when Denny represents the opposing side in court.