Act 1 The film opens eleven years prior to Infernal Affairs in 1991. Inspector Wong Chi-Shing (Anthony Wong reprising his role) is discussing the death of his first partner with an initially unseen companion, who is revealed to be Hon Sam (Eric Tsang, also reprising), the triad boss from Infernal Affairs. At this point in time Sam is a follower in Ngai Kwun's triad family and is also working as Wong's informant. Carrying a nondescript paper bag, a young Lau Kin-Ming (Edison Chen) makes his way through the streets of Mongkok. Ming stops at an ostensible martial arts school where Ngai Kwun is spending the evening. With a gun concealed in his paper bag, Ming kills Kwun and walks away.
Ming arrives at a secluded office space where Sam’s wife, Mary (Carina Lau), greets him. Mary is testing her new stereo system, playing the exact same song Ming used to test his system in Infernal Affairs; she sardonically praises it to Ming in the exact manner that Yan does in the first film while casually ascertaining whether or not he has any reservations about being Sam’s mole in the police force. Appearing aloof, Ming accepts the position and Mary packs a bag of cash for him, advising that he maintain a low profile and prepare for the police academy; assuming that the song she put on the stereo is distracting him, she also gives him a copy of it. Ming is attracted to Mary, but is unwilling to express it due to his lowly position in the gang. It is then revealed that Mary ordered Kwun’s assassination. Mary confesses that Sam has no knowledge of this transgression and urges Ming to keep it that way, as she wants Sam to take Kwun's place as leader of Ngai family triad.
Meanwhile, we see a young Chan Wing-Yan (Shawn Yue), his girlfriend and a young Crazy Keung (Chapman To) are waiting for something. Yan is a promising police cadet who has apparently assaulted and subdued Keung over a car theft. Superintendent Luk Kai-Cheung (Hu Jun) arrives on the scene with several officers. Luk admonishes Yan about his actions but decides not to report the incident to Yip, the principal of the police academy. Luk and Yan leave to attend a birthday dinner for Yip while Keung is sent to the police station. At the dinner, it is clear that Yip has high expectations for Luk as his successor and Yan as a police officer. A short time after the dinner, Yip and Luk are presumably driving home when they come across a heated argument between Yan and an Ngai henchman named Law Kai-Yin (Roy Cheung). Ngai Wing-Hau (Francis Ng), the middle son of Kwun, calmly explains that his father would have wanted all of his children to know if something were to happen to him; this includes Yan, a half-sibling. For using his mother's surname to hide his connection to the Ngai family triad, Yan is subsequently discharged from the Hong Kong Police Force. Yan is approached by Inspector Wong, asking why he wants to be a cop. The answer: "I want to be a good guy". This begins Yan's journey as an undercover agent in the triads as he is sent to prison by Wong in order to get close to Keung. Meanwhile, Ming joins the police force and goes through training ala the montage from the first film.
Hau has risen to take his father's place as triad boss, as he is the only Ngai sibling directly involved in the family business. With Kwun dead, all the triad bosses known as the Big Four, with the exception of Sam, scoff at Hau’s leadership capabilities and debate on whether or not to pay their tithe to the Ngai family. Hau, however, proves to be an adept and understated heir to Kwun and one by one blackmails the Big Four with his knowledge of their mutual betrayals. Sam has covertly remained loyal to Hau and acted as an agent provocateur in this affair, much to Mary's dismay.
Act 2 The second act takes place in 1995, with Yan out of prison as a small time gang member and Ming as a rookie police officer. Wong's partner, Luk, learns that Yan is the police mole and questions where Yan's true loyalties lie: with the police or with his half-brother. Yan's continual association with Sam and Ngai leads his girlfriend to have an abortion and we see Yan furious at losing the baby (Infernal Affairs tells us she did not abort it). She worries about the life he is leading and does not want their child to follow Yan's path. The ruthless yet honourable Hau wishes the troubled Yan to be integrated back into the Ngai family and invites him to his daughter's birthday party, where he brings him closer into the gang business as well. Ming’s path is considerably smoother; with Sam supplying information on criminal dealings Ming is able to apprehend numerous local gangsters, thus getting him promoted quickly.
At his daughter’s party, Hau tells the Big Four and Sam that he is retiring to Hawaii with the whole Ngai family and to divide his family business among them. He secretly rewards Sam for his years of loyalty by sending him to a contact in Thailand with the promise of total control over the cocaine racket, a business opportunity that the Big Four have not foreseen and of which he believes Sam will become a master. Next, Hau invites Yan to join him for his next dealing. Yan proceeds to relay this and other information he has collected on Hau, Sam, and the Big Four to Wong during a clandestine meeting. Luk, who had been tailing Wong, reveals himself and confronts Yan about his loyalties. Yan asserts that his only loyalty is to his mission.
In a hotel room, Mary is revealed to have conspired with Wong in the assassination of Kwun. Mary wants her husband in power and Wong wants an enemy he knows and can control. Meanwhile, Luk is organizing a strike team to catch Hau during his next dealing. When confronted by Wong about the sudden change of date for the operation, Luk confesses that he has had his own informant in the Ngai gang for 7 years, who tipped him off about a change in Hau's departure plans. Yan uses Morse Code to relay the location of the deal to Luk. Luk and Wong arrest Hau exchanging suitcases with two other men. It transpires Hau’s dealing was simply a ruse; the two men he met turn out to be private detectives he hired to investigate Kwun's murder. In Hau’s suitcase is videotaped surveillance of the meeting between Wong and Mary in the hotel room. This evidence becomes leverage to prevent the cops interfering with Hau's business.
Hau's real plan was to assassinate the Big Four and Sam, whom he believes is Mary's co-conspirator. The plan is put into motion as Hau is taken into questioning; the Big Four are killed off by various Ngai henchmen, an ambush awaits Sam in Thailand, and an assassin is edging toward Mary. Mary phones Sam, who is accompanied by Keung, revealing at the last minute that she arranged the hit on Kwun. Sam comes to grips with the reality of his situation and warns Keung to run at the first sign of trouble. With help from the clumsy and benign Keung, Sam escapes the ambush and takes one of the Thai gangsters (the Thai gang boss shown in the first film) hostage in the process. When Sam arrives at the airport, he tries to strike a deal with the Thai hostage while Keung attempts to warn Sam about trusting him. Sam offers his own gun to the gangster, believing in their friendship. The Thai regretfully apologises for his orders and shoots Sam.
In the aftermath of the assassinations, Hau rounds up and has Law kill three henchmen that Mary supposedly bribed to leave Kwun vulnerable. Hau then reveals that Law is an undercover cop before shooting him several times and pulling out his wire. As the bodies are burned, Yan takes a bullet for Hau in a drive-by shooting. Luk goes to Wong's apartment after he's acquitted in a tribunal hearing and forgives him for the murder conspiracy, but is then killed by a car bomb meant for Wong. Ming had saved Mary from the assassination attempt and they have been in hiding for two months. He reveals his true feelings for her and offers to protect her. She rejects his advances, as she is Sam's wife, and goes to Kai Tak Airport to fly to Thailand and find her missing husband. A bitter Ming is seen communicating Mary’s travel plans to an unknown recipient. Mary receives a phone call from Ming as she arrives at the airport, it distracts her long enough to be mowed down by car driven by Ngai henchmen.
Act 3 The third act is set in 1997 against the backdrop of the handover of Hong Kong to China. Ming is one of the officers involved with the ceremony and Yan has taken Law's place by Hau's side. Hau attempts to make the family respectable by going into politics but is arrested at a government party. The police have compiled enough evidence to bring Hau down, which rests on the testimony of a star witness – Sam, who survived the shooting in Thailand and apparently started a new family with a Thai woman. Wong brings Sam back to Hong Kong under witness protection and introduces him to the newly promoted Ming. Wong admits to Sam that at present the police only have enough evidence to imprison Hau for a few years; he then jokes that Hau would have to kill Sam to get life in prison. Sam and Ming talk for the first time in years.
Hau’s political aspirations disintegrate as his backers withdraw their support, and the Ngai family lawyer confesses that Hau has no legal chance of winning and resigns. On the defensive, Hau decides to immediately relocate the entire Ngai family to Hawaii while he awaits trial. Yan joins Wong where Luk has been interred and expresses his desire to get out of undercover work before his criminal persona consumes him. After giving Wong the last of the evidence against Hau, Yan salutes Luk’s headstone as Wong looks over to Yip in the distance. Within a few days of the trial, Sam escapes witness protection with Ming's help and confronts Hau and his gang alone. Hau has kidnapped Sam's Thai wife and child in order to prevent him from testifying. Sam outmaneuvers Hau, however, by revealing that his Thai friends are holding the entire Ngai family hostage in Hawaii. Through Wong, it is also revealed that the Thai woman Hau has hostage is actually Sam’s maid. Defeated, Hau holds Sam at gunpoint as Wong and a police squad arrive.
The climax of the film is a standoff between Hau's gang and the police, with Sam taunting Hau to kill him. As Hau shows signs of intent to fire his weapon, Wong shoots him. Hau collapses to the ground, dying in his half-brother's arms; moments before succumbing to his gunshot wound, Hau discovers the wire in Yan's jacket and that he is actually an undercover cop. In the aftermath, Wong questions Sam on whether he killed Ngai's family and condemns Sam’s tactics while Sam retorts that he did not expect to leave alive and the two men part ways. Before leaving, Wong reveals to Sam that he managed to get enough evidence to incriminate Ngai for life had he only been more patient. In his car Sam receives a call from one of his Thai friends, who turns out to be the gangster who shot him earlier. He asks Sam if he should “close” the Ngai case and Sam cautions that they not go too far. The Thai gangster explains that some things, like him failing to kill Sam, are fated and that to be powerful, they must be the ones who control fate. A remorseful Sam hangs up and the entire Ngai family, including the women and children, are executed.
The pieces are set in place for the original film: Sam goes down the dark path of replacing Hau as one of the most ruthless triad bosses, just as Mary had wished, and is now Wong's new foe; Ming is a police inspector, still working for Sam; and Yan is forced to remain as an undercover agent, following Keung over to Sam's gang. As the handover ceremony takes place, Sam is able to finally shed tears over the loss of his beloved Mary. Back in the police station, Ming handles a case involving a young girl coincidentally named Mary too (looking a lot like Sammi Cheng).
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