Henry Lee
Appearance(s):  Sleeping Dogs
Full name:  Henry Lee
Also known as:  Big Smile
Status:  Deceased
Gender:  Male
Date of death:  2012
Home:  Hong Kong
Nationality:  Chinese
Family:  Unnamed Daughters
Main affiliation:  Sun On Yee
Vehicle(s):  Jet 620V
Businesses:  Prostitution
Drug dealing
Voiced by:  Tzi Ma
"Making anyone other than me the chairman will be disastrous for Sun On Yee!"
―Big Smile Lee during the mission The Funeral.

Henry "Big Smile" Lee is the main antagonist of Sleeping Dogs. He is a Sun On Yee Red Pole, with ties to drugs, prostitution, and murder.



Lee started out in the Sun On Yee triad as an enforcer. At some point he was cut across the face, hence nick-named "Big Smile" because of the resulting scar. Lee took control of a small drug operation and began targeting upper class women and teenage girls, making them addicted to heroin, so that he could be able to exploit and force them into prostitution to support their addictions. This caught the attention of filmmakers and distributors, allowing Lee to use his girls as porn stars. With the profits, Lee laundered the money into larger drug operations and would use the profits to invest further in the entertainment and pornography industry. In just three years, Lee was in control of vast drugs, prostitution and pornography rackets.

As a result of his profits and rackets, Lee became a red pole and was the highest financed gangster in the Sun On Yee. Lee became a silent partner and investor in Sonny Wo's Three Circles Entertainment media business, spanning drugs and prostitution throughout Hong Kong’s entertainment industry. With Sonny as Lee’s chief economic backer, Lee was able to generate high revenue and immense cash reserves. Lee was also known for his use of excessive violence and brutality towards his enemies, traitors and even minor inconveniences. Making Liu Shen Tong his chief enforcer, specializing in torture and murder, Tong had killed undercover HKPD officer Charles Ho in this manner.

Events of Sleeping Dogs

Lee attempted to increase his power within the Triads by taking over Winston Chu's extortion and protection rackets in the night market. To do so, he enlisted Dogeyes Lin to steal Winston's business operations and assets, effectively creating civil war in the Sun On Yee between the Jade Gang and Water Street Gang, respectively. However thanks to Wei Shen, Winston not only resisted the takeover but even retaliated by attacking Dogeyes's drug manufacturing warehouse and kidnapped Siu Wah.

Dogeyes responded by attacking Winston and Peggy Li's wedding reception, hiring The 18K Triad, during which Winston and Peggy were murdered, and Uncle Po was shot and hospitalized. With the Water Street Gang seemingly leaderless, Lee sent his enforcer, Ponytail, to demand the full cut of the business operations that went to Uncle Po, which Shen refused, and incited a massive shootout and open hostilities. As a result, Shen was enlisted by Lee's main rival, Broken Nose Jiang. Wei and Jiang teamed up to ensure that Lee would not be elected the new chairman of the Sun On Yee.

Lee, along with Jiang, Two Chin Tsao, Pockmark Cheuk and Shen visited Uncle Po in hospital to discuss leadership of the Sun On Yee. Lee attempted volunteer and take control himself, but was interrupted by Jiang who nominated Tsao as temporary chairman, greatly irritating Lee. Jiang even suspected that Lee would murder Tsao, hence sent Shen to sabotage Tsao's home, and exploit his superstition, causing him to fall in "seclusion" for his own safety, as he viewed the position of temporary chairman unlucky. Shortly after, Uncle Po died while in intensive care leaving the position of chairman open.

"I am the strongest. I am the most feared. I say I should be chairman."
―Big Smile Lee

The Red Poles eventually arranged and attended a funeral service for Uncle Po, during which Sonny was arrested by Superintendent Thomas Pendrew and the Red Poles were attacked by an 18k hit squad, Lee and the others survived the violent shootout, prompting Lee to demand to be chairman citing that he is the most powerful and most feared. However Jiang, Pockmark and Wei argued that a formal election must be held in order to uphold the traditions and stability of the triad. This noticeably enraged Lee, who warned his fellow Red Poles to not vote against him.

Lee immediately retaliated by sending gangsters to attack the Water Street Gang, specifically to assassinate Wei. Lee's intent was to eliminate Jiang's supporters and potential votes against him in the election. Furthermore, Lee even had Jackie Ma kidnapped handed over to 18k, and buried him alive, to ambush and kill Wei.

After Wei survived Lee's attacks and rescued Jackie, Lee was tipped off by Pendrew of Wei's true status as an undercover cop. Lee responded by ordering Tong to torture and kill both Jackie and Shen in order to extract confessions to disgrace Jiang during the election. Jackie was killed, disemboweled, and hung from a pipe in an alley. However, Wei again survived and even killed Tong during his escape. Wei immediately responded with vengeance and went to kill Lee on the eve of the election. During a massive shootout, Lee fired a shotgun blast into Wei's shoulder and attempted to escape by speedboat to which Wei caught and held onto. Lee crashed the boat into a nearby fueling station, but Wei barely survived.
"How does it feel, pig? To know that your boss sold you out? Pendrew fucked you, Wei. Almost as bad as you fucked Jackie. You were supposed to die with Winston. Dogeyes blew that! And that pok gai, Tong... Fucking worthless (idiot)! But, that's okay... 'cause I'm gonna enjoy killing you myself."
―Big Smile Lee's last words
Enraged by Wei's interference and foiling of his plans to be chairman, Lee prepared to execute him, revealing that Pendrew double crossed him. However Wei knocked Lee's gun from his hand and finally beat him in a fistfight. Wei threw Lee into an ice chipper, killing him, and ending the long and violent civil war and allowing Jiang to become the chairwoman of the Sun On Yee.


As the most powerful and most feared Red Pole in Sun On Yee, Lee relied on two things: his use of extreme violence and his immense cash reserves. Lee is aggressive and short-tempered, hence is quick to resort to torture and murder with a lack of restraint, in fact his use of violence was viewed as too far even by Triad standards, making him both feared and disliked by other triad gangsters and fellow red poles. Lee's financial empire is worth millions, though his business methods are ruthless, through his distribution of drugs, and ruin the lives of many women by exploiting them for pornography, prostitution and occasionally human trafficking. Despite his brutality, Lee loves his family. He has several daughters he’s putting through college in the United States.

Lee is power-hungry, ruthless and arrogant to the point that he sees himself as the natural successor to the Chairman. However Lee is aware that he is disliked by other red poles, hence isn't foolish enough to leave his ascension to chance or an election. As a result, Lee has a complete disregard and disrespect for the rules and traditions of triad, and will do anything necessary for his own rise to power, even instigate civil war and working with the 18K to kill his fellow Sun On Yee comrades.

Mission Appearances

Sleeping Dogs


  • His name in Cantonese literally translates to "Older Brother".
  • In the final mission, Big Smile Lee reveals that he was the one indirectly responsible for everything that happened in the story (i.e. helping Pendrew cross Wei, convincing Dogeyes to attack Winston, increasing the civil war within the Sun on Yee by enlisting the 18K's help, and sending Tong to kill Wei and Jackie).
  • Tzi Ma, the Acto who Voiced Big Smile Lee, previously played Chinese Spy/Terrorist Cheng Zhi in 24.