Based on Robert B. Parker's novels. Jesse Stone is a New England police chief investigating a series of murders.
One moonlit night in Santa Monica, California, California, former Los Angeles Police Department homicide detective Jesse Stone (Tom Selleck) looks out at the ocean, waiting to sober up before driving across the country with his dog Boomer to the small coastal town of Paradise, Massachusetts, where he has been offered the position of police chief. Forced to resign from the LAPD for drinking on duty, Jesse knows that the Paradise job is his last chance. From a motel in Missouri, he calls his ex-wife, actress Jenn Stone, with whom he still talks regularly despite their divorce. Jesse's drinking problem became serious after he discovered that she was having an affair with her producer.
In the small town of Paradise, Massachusetts, Chief of police Jesse Stone (Tom Selleck) and his men investigate the death of teenage girl found floating in a lake. Officer Luther "Suitcase" Simpson (Kohl Sudduth) discovers a high school ring bearing the initials "HR". In the coming days, Jesse is haunted by disturbing dreams about the girl's murder. Since moving to Paradise, his private life involves drinking alone at his isolated house on the water with his dog Reggie looking on, occasionally talking on the phone with his ex-wife in California. Forced to resign from the Los Angeles Police Department for a drinking problem that began following his divorce, Jesse is still in contact with his ex-wife Jenn, who calls him regularly. Concerned about his drinking, she convinces him to see psychiatrist Dr. Dix (William Devane), a former detective and recovering alcoholic himself. Following his first session, Jesse visits the grave of his former girlfriend, Abby Taylor, for whose death he still feels deeply responsible.
In the small town of Paradise, Massachusetts, chief of police Jesse Stone is on the phone with his ex-wife Jenn in Los Angeles, who tells him not to call her that night. She's started seeing someone, who finds it strange that the two still talk every evening. Stone is dealing with other changes: his deputy, Luther "Suitcase" Simpson, is still in a coma from a head-wound he received in a supermarket robbery; his other deputy, Molly Crane, resigned from the force to have a family. Her replacement, Rose Gammon, is learning to deal with Stone, as she had once worked for his predecessor.
Jesse Stone and Captain Healy are shot during an unauthorized stake-out in Boston. Meanwhile, a cryptic letter sent from Paradise leads the mother of a kidnapped child to Stone. Though her son was declared dead, she hopes he will reopen the case.
Police Chief Jesse Stone, who was suspended by the Paradise, Mass. Town Council, begins moonlighting for his friend, State Homicide Commander Healy, by investigating a series of murders in Boston, leaving Rose and Suitcase to handle a crime spree in Paradise on their own. Jesse pours his energy into his work in an effort to push away his twin demons: booze and women. When his investigation leads to notorious mob boss Gino Fish, Jesse's pursuit becomes hazardous
After being replaced as the chief of police in Paradise, Massachusetts by the town council president's son-in-law, William Butler (Jeff Geddis), Jesse Stone is still without a full-time job (though he vows to one day be reinstated). Nevertheless, he continues to find ways to pursue investigations into two separate murders: one involves a friend with whom he had lost contact, and the other has him working as a consulting investigator for the Massachusetts State Police Homicide Division on a case involving a robbery and murder suspect. Both Jesse and his friend, State Police Captain Healy (Stephen McHattie), have doubts as to the robbery/murder suspect's guilt. All the while, Jesse deals with tensions between Butler, who expects him to give up his "concealed carry" gun permit, but who is informed, by Rose Gammon (Kathy Baker), that as a retired (not fired) police officer he has a federally mandated right to "concealed carry" for life. His problems with his ex-wife, and drinking issues are still present.
Jesse Stone still misses the Paradise, Massachusetts police chief position, which he lost because the current town council president, Carter Hansen (Jeremy Akerman), wanted his son-in-law, William Butler (Jeff Geddis), to have the job. A suspicious police cruiser explosion kills chief Butler and officer DeAngelo (Vito Rezza). Curiously, the former town council president, Hastings "Hasty" Hathaway (Saul Rubinek), appeared to know about the incident before the current town council president was officially notified. Jesse is reinstated as "temp chief" by Hansen and uncovers apparent (but unproved) police corruption involving Butler. Jesse discovers a possible clue: the characters "2AH10" written on the April 24 page of Butler's desk calendar.
Police Chief Jesse Stone accepts a position as an unpaid consultant with the Massachusetts State Police Homicide Unit, working for Lt. Sydney Greenstreet who gives him case files on several murders. He accepts the job to relieve the boredom he has been feeling due to the lack of any significant crime transpiring lately in the town of Paradise. Jesse has also been lonely because his dog recently died. After reviewing the files, Stone takes special interest in one case that involves the fourth victim of a brutal serial killer who slashed and disemboweled his victims while they were still alive. The jailed killer, a man named Richard and known as the "Boston Ripper", admits to the first three murders with pride, but maintains he did not commit the fourth murder. After interviewing the killer, Stone concludes that he's a "sick son of a bitch", but does not believe he killed the fourth victim, Mavis Davies.