Second Season Opener Isaac returns to the job, but the effects of his stroke appear to be affecting his performance. The 90-day ""cooling off period"" following Dana's canceled wedding is drawing to a close, and Dan encourages Casey to ask Dana out. Natalie and Jeremy fight over a job she's offered in Galveston, TX.

Rumors abound that a ""ratings guy"" is being brought in to raise the show from its third place status. To Dana's suprise, Isaac announces the rumors are true. Dana has an ""epiphany"" that she and Casey should date other people for six months. Dan is invited to a Hillary Clinton fundraiser, and in his efforts to impress the First Lady, confuses secular with non-secular in a conversation about schools. This causes him no end of distress, and he proceeds to obsess about it to Casey.

With Sam Donovan around stiffness ensues both on and off the set. Dana debates leaving the show, after she feels everyone is blaming her for the shows problems. Natalie tells her that if she goes she has to bring her, and Jeremy, and Dan, and Casey. The tension grows, when the network bosses demand that the staff meet with J.J. and his boys for some notes. Sam is offered Isaac's job but he turns it down, and tells them where to go, thus showing he does have feelings.

Jeremy becomes concerned when he finds out Natalie is writing to his deaf sister Louise. Dan and Casey become, very competitive about an Internet poll, over whose cooler. Casey convinces Jeremy to rig the computer to vote for him 2,000 times a minute. When Dana goes out with an old friend from high school, Cab Calloway, Casey is angry. Dana as a spur of the moment action takes off her underwear during the meal.

Jeremy tells Dana that there is no reason to hire people to prepare for the expected Y2K computer problems; he has made the computers Y2K compatible. To prove this, Jeremy, rigs the computer to say that it is December 31, 1999 and hold a Y2K test to prove that there will be no computer problems when the studio rolls into 2000. The results are total darkness. Dan picks up a therapist in a bar, who invites him out on a date... he thinks, she really just thinks he needs some therapist.

Natalie obsesses over the loss of hell. In a nod to real-life racist John Rocker, Casey interviews an old friend, Shane McArnold, who heaps disdain on his new home city of New York and all its inhabitants. Casey promises to ""fix it"" out of loyalty, but Dana knows it's good television and leaves it as is. Meanwhile, Dan's therapist Abby is opening up Dan's true feelings about his family, making him more and more dysfunctional.

Dana is extremely proud when her brother gets two sacks in a football game. She becomes determined to show others how he did it. Jeremy is nervous about firing Corbin Davis, a cousin of JJ's who is screwing up simple assignments. Jeremy gives him a pep talk and Corbin tells him, that he doesn't take sides when JJ talks bad about this show. Because of a drug scandal involving football players erupts, Casey travels to Ohio to find out the names, Tina fills in. When the names are uncovered, one hits close to home for Dana... literally... her brother.

Dana gets edgy as the arrival of her brother comes close. As part of a Secret Santa, Casey searches for the perfect gift for Isaac. Natalie tells Casey that if his gift isn't cheap and located within two blocks of the building he's getting socks. When Natalie gives Dan a tape to watch of her work as an anchor, he tells her it was great, when it really was just mediocre. The crew struggles to name an athlete of the century. Dan decides to go to midnight mass, even though he's Jewish.

Dana worries when Casey goes out on a date. Jeremy's optimism about his award nomination fades.

Casey goes out with Pixley again much to Dana's dismay. Dan wants to do a story on the amazing World Series win by the Giants in 1951, and finds out that Isaac was actually at the game, although he missed the key home run. When Casey finds out Isaac never told him, but told Jeremy he questions their special bond.

While prepping to cover a major fight, Dana and Casey duke it out over their stalled fling, and Dan's dad, Jay, hits town for a tense visit. But after the match goes south, the CSC staff bands together to knock out a killer show, including an hour's worth of coverage of a fight that lasted under a minute and a correspondent who only will respond to being called ""the cut man"", calls Dan; Casey, and Casey; Dan. He also shows he has no idea what he is talking about, when he talks about the last winner of the Miss America pageant, Miss Rochester.

The crew is excited when they get a chance to interview Michael Jordan; that is until the strings began to be attached. First they find a paper in the press packet, that coaches Michael how to steer away from sports questions, next they are told to only talk about his new cologne, and then they get a request for total editorial control to Michael. They drop the interview when they discover that they were picked because of their ratings vulnerability. Sam returns and sets Dana into a frenzy, he later meets Sally. Casey frets over what to do in front of Charlie's class, when he is invited to show and tell.

Natalie and Jeremy fight over going to a club. Dan finagles the night off. A substitute anchor can't do his job because of his girlfriend. Dana and Sam share a moment.

Jeremy and Natalie's break-up ripples through the show after Jeremy asks for his ""stuff"" back. Casey's dilated pupils provide comic relief for Dan and the crew. Dana deals with Sam's imminent departure. A riot breaks out at Madison Square Garden and Natalie questions turning over the show's filmed coverage of the event to the police.

The staff prepares for a game of ""Celebrities"". Jeremy, feeling left out, goes to the bar and makes a new friend, then panics when he realizes who she is. Isaac, despite his vast knowledge of American popular theatre, cannot recall the lyrics of ""How Are Things In Glocca Morra"".

Dan decides to skip therapy and spends an hour in Abby's office telling her so. Jeremy e-mails the porn star he blew off, then decides to tell her in person why he's not going to see her again. Casey decides to bribe the gang with international cuisine to get them to watch a track and field event in the wee hours. Dana decides to seek shelter from a rainstorm in church.

Casey and Dana try to psyche each other out as they prepare to make their NFL draft day predictions. Dan gets glum when his golf date with PGA star David Duval is jeopardized - by his job. Jeremy tells Natalie about Jenny - except for the part about her being a porn star. Casey questions Dan's attitude and Dan questions their relationship.

As NFL draft day unfolds, relationships unravel. Jeremy anguishes over Jenny's visit to the studio, where she and Natalie discover common ground and she and Jeremy come apart. After giving him a talking-to behind closed doors, Casey is stunned when Dan humiliates him in front of millions.

The network deals a financial blow to ""Sports Night"" that has Isaac and Dana reeling - the show's Olympic coverage is going to be cut to the quick and Natalie's job may be cut entirely! Depressed about his disgraceful on-air behavior toward Casey, Dan decides to hold a Passover Seder, which Jeremy turns into a theatrical event that has a healing effect on everyone.

Upset when Natalie gets a job interview with Saturday Night Live, Dana encourages everyone to undermine her confidence. Dan's publicist wants him on the PR fast track - starting with an appearance in New Jersey! Casey and Jeremy roll up their sleeves and try to get to the bottom of CSC's financial woes. Isaac stresses over his stroke's effect on his grandson.

While at Anthony's trying to drown their fears about the future of ""Sports Night,"" Dana meets a mysterious stranger who seems to know a great deal about the bidding for Continental Corp.; and Dan tries to convince Casey that a move to LA might not be a bad thing.

Bidders drop out of the auction for Continental Corp., which causes concern for the future of the ""Sports Night"" team. Meanwhile, Casey prepares to look for new work without Dan, who is reunited with a familiar face from his past.