Jesse Stone is the police chief of Paradise, Massachusetts, a small town north of Boston. He was previously a homicide detective in Los Angeles, but was fired due to a drinking problem following his divorce. He has a physical relationship with a lawyer named Abby Taylor, who is on the town council.
One night, a body is found on the shoreline, shot with a .22 caliber weapon. After two more murders with the same method, an eyewitness comes forward who saw a red Ford Explorer leaving the scene of the third crime. The Explorer is registered to a man named Andrew Lincoln, who is on the list of .22 caliber gun owners in Paradise.
Andrew and his wife Brianna are revealed to be middle-aged thrill killers who murder random people and film their crimes for their own pleasure. Jesse investigates the rape of a high school girl and brings the perpetrators to justice. The Lincoln's begin stalking Abby and eventually kill her, causing Jesse to devise a plan to encourage them to try to kill him as well.
He meets with Andrew at the scene of the second crime and Candace's house, where the Lincolns had planned to kill her, is under surveillance. The Lincolns attempt to kill Jesse, but he is able to defend himself and they are arrested.
Jesse Stone, a former LAPD detective, takes a job as police chief in the small town of Paradise, Massachusetts. He is offered the job despite being drunk at his interview and is suspicious of the circumstances surrounding his hiring and the sudden retirement of his predecessor. As he begins his new role, Jesse meets Joe Genest, a thug who works with Boston gangsters in a money laundering operation and provides muscle for the corrupt town council chair, Hastings "Hasty" Hathaway. Genest taunts Jesse and tells him that the restraining order Mrs. Genest has against her husband is useless because his expensive lawyers can easily have it overturned. Jesse responds by kicking Genest in the groin and threatening to do more if anything happens to Mrs. Genest. The next day, Jesse is visited by Abby Taylor, the attractive town attorney and member of the board of selectmen, who scolds him for assaulting Genest. Jesse and Abby begin a physical relationship, although it is also filled with genuine affection.
Meanwhile, Genest becomes concerned that the former police chief, Lou Carson, will reveal the money laundering operation and follows him in a truck, pushing his car off a cliff and killing him. Genest then demands half of the money laundering profits from Hathaway, who is now an accomplice to murder. Genest also starts harassing Jesse, damaging his police car and following him around town. State homicide inspector Captain Healy visits Jesse and tells him about Carson's death, believing it was an accident due to the alcohol found in Carson's blood. Jesse, however, thinks otherwise.
As Jesse investigates the circumstances of Carson's death, he becomes increasingly convinced that it was a murder and that Genest and Hathaway are involved. He also begins to suspect that they are having an affair. Genest, who is becoming increasingly unhinged, attacks Jesse and nearly drowns him in a whirlpool, but Jesse is able to fight back and arrest Genest. Hathaway, realizing that Jesse is onto him, tries to flee town but is caught by Jesse and arrested as well. In the end, Jesse's hard work and determination lead to the uncovering of the money laundering operation and the arrest of Genest and Hathaway. Despite his personal struggles with alcohol and his complicated relationship with Jenn, Jesse is able to find some level of happiness and closure in Paradise.
In the small town of Paradise, Massachusetts, Chief of Police Jesse Stone investigates the murder of a teenage girl found floating in a lake. While working on the case, Jesse meets with the headmistress of the girl's high school, Dr. Lilly Summers, and becomes romantically involved with her. He also deals with a domestic violence case involving a man named Jerry Snyder, who beats his wife.
Jesse's investigation leads him to a local writer named Norman Shaw, who has ties to the Boston mob and is suspected of having a predilection for young girls. Shaw becomes the prime suspect in the girl's murder and Jesse eventually gathers evidence to arrest him.
DNA from Shaw's cigar confirms that he was the father of the girl's unborn child. Shaw is arrested and confesses to the murder. As the case is closed, Jesse continues to deal with his personal struggles, including his drinking problem and the guilt he feels over the death of his former girlfriend.
In the small town of Paradise, Massachusetts, chief of police Jesse Stone is dealing with several changes in his personal and professional life. His deputy, Luther "Suitcase" Simpson, is in a coma after being injured in a supermarket robbery, and his other deputy, Molly Crane, has resigned to start a family. Stone's replacement, Rose Gammon, is adjusting to working with Stone. Stone struggles with alcoholism and is advised by his psychiatrist to find a way to occupy his time and make it important. He decides to investigate a cold case involving a bank teller who was killed during a robbery in 1992.
During the investigation, he discovers that the robbery was actually a cover-up for a money laundering scheme. Stone also investigates the case of a young woman who claims she was raped by an older man on his yacht, and he obtains a video that shows the woman consenting to the sexual encounter. As Stone continues to investigate the cold case, he becomes attracted to the sister of the victim, who is actually the victim in disguise.
The sister reveals that she and her sister planned to steal money from the bank as part of the money laundering scheme, but the plan went wrong and the sister was killed. Stone helps the sister turn herself in and resolves the case.
Captain Healy, a state police officer, is attacked but is saved by Jesse. Jesse begins investigating the shooting against the wishes of the town council, who are concerned about Jesse's involvement in six previous shooting incidents and do not want him to further stretch the already thin police department. Jesse continues to investigate and receives information from Sister Mary John about a possible link to underage prostitution. Jesse follows and confronts Teddy Leaf, a suspect, and gets him arrested for breaking and entering and carrying a weapon, putting him in jail for a long time.
Jesse continues to communicate with Jenn and attend therapy, forming a friendship with his therapist, Dr. Dix. Jesse also begins sleeping with Internal Affairs officer Sidney Greenstreet.
The film follows Jesse Stone, a suspended police chief who has become alcoholic and isolated, as he is recruited by his friend and state police homicide commander, Captain Healy, to work as a private consultant on the investigation into the shooting murder of a young man in a parking garage.
Stone learns that the victim had ties to Boston mob boss Gino Fish and begins to suspect that Fish's secretary, Alan, may have committed the murder out of jealousy and then killed two more people to make the events appear to be related and the work of a serial killer.
Stone confronts Gino and Alan with his conclusions, leading to Alan's death in a hit and run. Stone and Healy speculate that Gino ordered the hit to protect his reputation in the underworld.
Jesse Stone, the former chief of police in Paradise, Massachusetts, has been replaced by William Butler, the town council president's son-in-law. Despite being without a full-time job, Jesse remains determined to one day be reinstated as chief of police. In the meantime, he continues to investigate two separate murders: one involving an old friend and the other 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, have doubts about the suspect's guilt. Jesse also faces tension with Butler, who wants him to give up his "concealed carry" gun permit, but is told by Rose Gammon that as a retired police officer, Jesse has the federally mandated right to "concealed carry" for life. Jesse's problems with his ex-wife and his drinking issues persist.
Jesse Stone is a former police chief of Paradise, Massachusetts who was replaced by William Butler, the son-in-law of the current town council president, Carter Hansen. However, a police cruiser explosion that kills both Chief Butler and Officer DeAngelo leads to Jesse being reinstated as temporary chief. As he investigates the incident, Jesse discovers possible corruption involving Butler and finds the clue "2AH10" written on a page of Butler's desk calendar. He tries to reunite his team, including Deputy Luther Simpson and assistant Rose Gammon, but they have moved on to other jobs. State Homicide Commander Healy, psychotherapist Dr. Dix, and sales associate Thelma Gleffey also assist Jesse in the case. Gino Fish, a local involved in illegal drug trafficking, is also a suspect. Jesse learns about an assassin named Arthur Gallery who has been following him and eventually confronts Hasty Hathaway, the former town council president and a convicted felon, who is revealed to be the true drug kingpin and Gino's boss. Hasty escapes and is wanted for drug distribution, money laundering, and conspiracy to murder. In the end, Simpson returns to work with Jesse and it is implied that Rose may also return. Jesse's position as chief is made permanent.
The title "Benefit of the Doubt" refers to the belief that police officers suspected of corruption should be given the benefit of the doubt until proven otherwise.
In this story, Police Chief Jesse Stone takes on a consulting role with the Massachusetts State Police Homicide Unit to investigate a series of murders. Stone becomes particularly interested in the case of a serial killer who claims to have committed the first three murders, but not the fourth. Stone interviews the killer and concludes that he is "sick," but does not believe he is responsible for the fourth murder. Stone also takes an interest in a teenage girl named Jenny, who he finds smoking marijuana in a park, and investigates her home life, finding that her mother is abusive. As Stone continues his investigation, he becomes suspicious of a police detective named Leary and believes that he may have killed the fourth victim, Mavis Davies, with whom he was having an affair. Stone eventually confronts Leary and proves his guilt, leading to his arrest.