After Robin's husband dies, she gets angry when his will seems to stipulate that Kelly should resume his duties as her bodyguard. Meanwhile, Sipowicz must clear his own son of a drug pushing charge. While investigating a tip on the location of a dead woman, Medavoy, Martinez and Kelly find another body of a dead man in a garbage dump which leads to Kelly suspecting a hotel concierge and the hotelier of conspiring to murder the hotelier's husband.

Simone deals with an emotionally fragile woman, named Joyce Novak, whom is a witness for a double-murder when she keeps changing her story, for she is really only interested in flirting with him. Meanwhile, Sipowicz participates in the investigation where a family-run business, that he used to work in, is held up and the owner's wife is killed. After Donna leaves town for a long vacation (and to get away from the annoying Medavoy), her temporary replacement, John Irvin, is a flamboyantly gay man whom Simone used to know from his old precinct. But Irvin makes the whole the station, including the bigoted Sipowitz, uncomfortable. Also, Martinez enters in a police department boxing tournament.

Medavoy starts a bet with Sipowicz to see who can lose the most weight in a single month. Afterwards, Sipowicz and Simone help out Detective Stuart Morrissey on his investigation in the case of a missing baby. Meanwhile, Martinez campaigns to become the elected delegate for the squad and his opponent, Detective Vince Gotelli, is determined to win the seat himself. Also, Simone makes a deal with Henry to let him share ownership of the building.

An ex-con that Sipowicz put away a year ago approaches him and tells him about a prisoner who's been serving time for a crime he didn't commit and he and Simone decide to reopen the case. Meanwhile, Martinez wins the election by just three votes, much to Gotelli's chagrin. Simone comes across Detective Nick Savino who helps him with the investigation of the murder in his building and Savino suspects Henry has something to do with it. Fancy gets a cavity filling which makes him more edgy than usual and Medavoy loses one pound more than Sipowicz. Also, Russell still has not come to any conclusion about her relationship with Simone.

Simone and Sipowicz look into the death of a limo driver and try to find his last clients which included a gay businessman trying to cover up his secret cruising lifestyle. At the same time, Sipowicz finally lodges a complaint against Geri that gets her moved up to the crime lab area, while Gina is transferred down to the squad floor. Meanwhile, a new detective, Jill Kirkendall, joins the squad. Her first case involves investigating a man whose life is being threatened and this leads Kirkendall to suspect that the man's assailant's girlfriend has a stolen infant. Simone gets the approval from Detective Savino to question Henry about the apartment shooting and finally gets the real story. Also, Russell can't figure out how to talk to Simone about her current assignment.

Sipowicz returns to work after his successful prostate surgery, but apparently too soon, for he has an accident while interrogating a suspect. He is given desk duty to help Simone and Russell investigate the murder of a woman's boyfriend by her ex-husband, the ex-husband later revealed to be searching for his daughter who's gone missing while in the ex-wife's care. Meanwhile, Simone is called upon by Detective Nick Savino to help investigate a missing persons report that is being filed by the nephew of one of Simone's apartment tenants. Based upon past exchanges between the missing woman and Henry Coffield, another building tenant, Coffield becomes a suspect. Former administrative aide Naomi Reynolds shows up at the station, now wearing a private security uniform and speaking in her natural Australian accent, to visit Simone, hoping to tell him that her situation with the INS was resolved and she is now furthering her pursuit to one day become a NYC police officer.