|Full name:||Raymond Mak|
|Main affiliation:||Hong Kong Police Department|
|Voiced by:||Byron Mann|
- "We're cops, there are rules."
- ―Raymond Mak to Wei Shen
Raymond is a dedicated police officer within the Hong Kong Police Department and holds the rank of Detective. Along with Thomas Pendrew, Raymond's primary focus was to bring down Hong Kong's most powerful and dangerous Triad, the Sun On Yee. However, their previous undercover operative, Charles Ho, failed to remain undercover, and was subsequently tortured and killed by ruthless triad enforcer Liu Shen Tong, prompting both Pendrew and Raymond to find a new suitable candidate. Pendrew decided to recruit San Francisco Police Officer, Wei Shen, who already had a distinguished file and career in undercover work. However, Raymond requested and reviewed all of Shen's personal and psychological files, and concluded that Shen would be unsuitable due to his personal vendetta, making him a liability. Despite Raymond's objections, Pendrew recruited Shen, viewing him as the perfect candidate.
Events of Sleeping Dogs
- "Our intel suggests that Winston is looking for muscle. You need to find a way to make him trust you."
- ―Raymond to Wei
Raymond and Pendrew met with Shen after he made contact with Water Street Gang associate Jackie Ma after a planned arrest, instructing him to infiltrate the Sun On Yee, and tasked him to ultimately bring down the Triad's leader, the Dragon Head, lieutenants, and the Red Poles, starting by getting close to Winston Chu, leader of the Water Street Gang. Pendrew assigned Raymond to be Shen's handler, reporting to him of his progress. However, Raymond and Wei got off to a rocky start, when Mak bluntly expressed his skepticism of Shen's ability, warning him that Hong Kong Triads are more dangerous than American-Asian gangs that he has dealt with before; furthermore, Raymond cited to Pendrew Shen's history of excessive violence and his personal vendetta, though Pendrew was still convinced that Shen was perfect for the assignment.
Raymond met with Shen not long after the latter successfully became part of Winston Chu's Water Street Gang. Shen reported details of the civil war between Red Poles Winston and Dogeyes. However, Raymond was concerned over Shen's state of mind, warning him to keep his objectivity as a police officer, to which Shen retorted that he is an undercover cop, hence doesn't follow the same rules as Raymond.
They next met after Shen's meeting with Uncle Po. Raymond expressed strong disapproval for letting Siu Wah go instead of arresting him, and warned Shen that he would use his authority to terminate the operation for crossing the line, strongly doubting his objectivity. However, Shen revealed that he used Siu Wah to gain leverage in the organization and now has even personally met the Chairman of Sun On Yee himself. Raymond conceded that Shen was indeed gaining results and was noticeably surprised with Shen's progression.
- "That's what worries me, Wei. You're one of them."
- ―Raymond to Shen
After the wedding massacre, Shen explained that he was now promoted to Red Pole and was even in a better position of power in the Sun On Yee. However, Raymond was again concerned for Shen's emotional well-being and was even worried that by being too close within the Triad, his loyalties might change.
After Shen's formal initiation into the Sun On Yee, Raymond instructed Shen to gain information on Sonny Wo, that would lead to his arrest, rationalizing that he was one of the main sources of revenue that needed to be cut off. Raymond also arrested Shen's associate and friend, Jackie, for information, despite Shen's objections to maintain his cover. Raymond also questioned Wei about the disappearance of Dogeyes, who, in actuality was kidnapped by Wei and murdered by Mrs. Chu for his involvement in the wedding massacre. However, Wei remained tight-lipped and told Raymond that he had no idea about what happened to Dogeyes.
- "Wei, you've crossed Pendrew. He's cut you off. This is your last chance to come in clean."
- ―Raymond to Wei in Buried Alive
However, the civil war within the Sun On Yee continued to escalate. Pendrew betrayed Shen to the 18K Triad at Uncle Po's funeral and could potentially ruin his cover. Raymond requested to Shen to back out of the Triad, concerned for his safety, however, Shen refused, and left in order to rescue Jackie and stop Big Smile Lee.
After killing Big Smile Lee, Shen was taken in by Raymond into protective custody. After Shen informed him that his cover was blown by Pendrew, Raymond revealed that Pendrew was promoted in Interpol for convicting Sonny and thus was too high up to be challenged. Nonetheless, Raymond congratulated Shen for bringing Big Smile Lee to justice and closing the case, ending their partnership on good terms.
Wei later received hospital security footage from Broken Nose Jiang that showed Pendrew personally murdering Uncle Po by injecting lethal chemicals into his IV bag. Wei used the footage to incarcerate Pendrew, ending Pendrew's career.
Raymond is a model police officer, very obedient and loyal, following police rules and procedures to the strictest and fullest of his ability. As a result, Raymond exercises extreme caution in police work and avoids risk whenever possible. In fact Shen even criticized Raymond for not getting results, describing him as a desk jockey. Raymond and Shen do not see eye-to-eye on many matters at first, as Raymond views Shen as a liability. Raymond questions Shen's actions and loyalty, but eventually comes to realize and is impressed by his ability, accomplishments and dedication in his assignment. This leads to Raymond becoming more concerned for Shen's well being. In the end, Raymond and Shen come to an understanding and develop mutual trust and respect between each other.
- Welcome to Hong Kong
- Club Bam Bam (Post-mission Text/Meeting)
- Listening In (Voice/Boss)
- Chain of Evidence (Voice)
- Uncle Po (Post-mission Text/Meeting)
- The Wedding (Post-mission Text/Meeting)
- Initiation (Post-mission Text/Meeting)
- Conflicted Loyalties (Text)
- Buried Alive
- The Election (Voice, Flashback)
- Big Smile Lee