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Events of Sleeping Dogs
- "Winston, I don't like this cocky little fucker!"
- ―Conroy upon meeting Wei Shen
After Jackie Ma reconnected with Wei Shen in jail, Wei showed interest in helping Jackie and joining the Water Street Gang, all as a part of an undercover plan to infiltrate the Sun On Yee from the inside. As Jackie introduced Wei to Winston at the Golden Koi, Conroy showed great hostility and suspicion towards him, calling him an outsider. However, Winston was impressed with Wei, and instructed him to go with Conroy to the Night Market. Conroy, along with Duke and Vincent, attempted to haze Wei by fighting him, but Wei survived, managing to fight them off.
- "I'm watching you new guy. If you fuck up..."
- ―Conroy to Wei in the Night Market
Shortly after, Dogeyes Lin came to taunt Winston and Wei. Winston, furious, ordered Wei and Jackie to retake the Night Market from Dogeyes and extort protection money from the vendors. After Wei was successful, Conroy was still unconvinced, as he confronted Wei, threatened him, and told him that he would be keeping an eye on him going forward.
Conroy accompanied Wei in taking over the Marlborough Drive minibus route from Dogeyes. During their assignment, Conroy, discussed the gruesome death of undercover officer Charles Ho, and how infamous Sun On Yee enforcer Mr. Tong buried him alive. Conroy remarked to Wei that he knew how to spot a traitor, and was suspicious of Wei for being an undercover officer because of his reluctance to kill anyone.
- "You come in out of nowhere and suddenly our guys start to get arrested? He ratted out Popstar, Winston! I know he did!"
After Wei's undercover work led him to take down a Sun On Yee ketamine dealer named Popstar, Winston called him to the Golden Koi. Conroy and Winston held him down, along with Duke and Ming, a low level Sun On Yee dealer. Convinced that Wei was behind the incarceration of Popstar, and that he was an undercover officer and a snitch. However, Wei was able to deflect suspicions onto Ming since he would benefit the most from the incarceration of Popstar. Winston angrily assumed Ming to be responsible and working for Dogeyes, hence shot Ming in the head, killing him. Winston told Wei that loyalty was important, and threatened that if he was not loyal, he would end up with a similar fate.
- "You showed your true colors tonight, brother."
- ―Conroy to Wei Shen
The fight between the Water Street Gang and Dogeyes' Jade Gang continued to escalate after Dogeyes shot up the Golden Koi, Winston ordered Wei, along with Conroy and the Water Street Gang, to destroy Dogeyes' drug manufacturing plant and kidnap Siu Wah, the operator. Conroy told Wei that he wanted Wei to kill the drug dealers and workers at the plant to prove that he was not a cop. Wei did so and was also successful in kidnapping Siu Wah, with Conroy and the others burning down and destroying the manufacturing plant. After they completed the task, Conroy, realizing Wei's skills and loyalty, apologized to him for his animosity towards him.
- "Winston's gone. Right now we gotta stick together."
- ―Wei to Conroy and Jackie
Just a short while later, Winston was killed at his own wedding, in an attack by the Jade Gang, posing as the 18K Triad (in turn posing as the wedding staff) and led by Johnny Ratface, a mission planned by Dogeyes. Conroy and Jackie were arguing in Club Bam Bam about the next course of action for the gang, when Ponytail, an enforcer for Big Smile Lee came into the club. He told them that, while they were allowed to continue their operations, that the cut previously belonging to Winston would now go to Lee. Wei refused, threatened Ponytail, and a massive gunfight ensued. Wei later met Broken Nose Jiang, a red pole, due to their compatibility and mutual dislike for Big Smile Lee, offered support to Wei and the Water Street Gang.
Conroy was also present at the initiation ceremony of Wei and Jackie, as Uncle Po's chief advisor, Pockmark Cheuk, formally initiated them into the Sun On Yee. Shortly after, Uncle Po was assassinated, leaving the position of chairman vacant, prompting an election, in which Big Smile Lee considered himself the obvious candidate.
- "Big Smile Lee's coming after us. I guess he figures we can't vote against him if we're dead."
- ―Wei to Conroy
Lee attempted to intimidate or murder anyone who would not vote for him, hence he sent his men to attack Wei, Conroy, and the Water Street Gang. Wei and Conroy managed to fight them off, first in a brutal hand-to-hand fight in Tran's chop shop, leading to a vicious gunfight at the Golden Koi, which spilled into the streets. After the fight, Wei and Conroy managed to convince Ricky Wong, a close partner to Lee, to support Wei instead of Lee. Wei told Conroy to go into a low profile with the Water Street Gang before the election. Wei later killed Big Smile Lee, ending the long and violent civil war.
Conroy is described as "pure muscle" and as a thug. He is aggressive, short tempered and violent, but he is often kept in check by Winston. However, he is hardly even intimidating to Wei and is often a nuisance to Winston who quickly loses his patience with him. Like Winston, Conroy is also a steroid user, is aggressive, relies on brute force and isn't particularly intelligent, in fact Winston had little faith in Conroy's ability to lead the gang. This reflects the Water Street Gang's lack of sophistication and poor standing as the weakest faction in the Sun On Yee. At first, Conroy treats Wei with suspicion, hostility and even jealousy, though Conroy eventually develops respect and admiration for Wei. Conroy proves himself to be a capable and trusted subordinate and friend to Wei.
- Welcome to Hong Kong
- Vendor Extortion
- Mini Bus Racket
- Club Bam Bam
- The Snitch
- Listening In
- Uncle Po
- Meet the New Boss (Boss)
- Civil Discord (Boss)
- The Election (Flashback)
- Big Smile Lee (Voice, Flashback)