In Sleeping Dogs, side content often adds as much flavor to the story as the main missions themselves — and nowhere is this more true than in the morally murky world of Roland Ho. Acting as a loan shark’s muscle, Wei Shen steps into the role of enforcer across a series of favors for Roland, putting pressure on deadbeats, gamblers, and small-time hustlers who’ve gone too far into debt. What begins as routine strong-arm work soon spirals into ethically questionable territory, ending in a dramatic and sobering turning point.

This guide walks you through the entire Roland Ho side mission chain, with a focus on tactics, notable encounters, and the gradual narrative arc that transforms Wei’s role from thug to reluctant conscience.

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First Job: Finding Samson Gao

Roland’s first target is Samson Gao, hiding out on an overpass in North Point. He believes he’s invisible — but Roland has eyes everywhere. After being confronted, Samson tries to deny everything but quickly folds under pressure. Your role is simple: find him, confront him, and make sure he understands it’s time to pay.

The encounter is straightforward but introduces you to Roland’s brand of justice. Calm threats, intimidation, and a touch of menace — it’s less about brutality and more about presence.

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Second Favor: Teaching Yang a Lesson

Next up is Yang, a massage parlor owner who never seems to have Roland’s money despite a steady stream of clientele. He hides behind bravado, claiming connections in the police and pretending to be untouchable. But Wei knows better.

This mission ups the ante by involving intimidation in front of witnesses. Yang’s false sense of protection crumbles as Wei storms through his business. The key here is pressure — assert dominance quickly before he can bluff his way out.

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Creative Solutions: $10 Actors and Public Humiliation

In a humorous yet effective tactic, Wei hires two bystanders for $10 each to pose as potential customers. Their presence escalates the situation, shaming Yang in front of others and shattering his confidence. It’s a clever, non-violent method that illustrates Wei’s growing ingenuity in these confrontations.

Public spectacle becomes a weapon — a subtle nod to how reputation and shame carry as much weight as fists in this world.

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Third Job: The “Broke” New Car Owner

Roland’s next debtor claims poverty, but a shiny new car tells another story. Wei calls him out, leading to a desperate chase and forced confession. The debtor eventually breaks and agrees to pay, but not before offering up flimsy lies about the car belonging to his mother.

These missions are about reading the room: lies, fear, and desperation are layered beneath every excuse. Wei’s street smarts let him cut through them.

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A Complication: Tommy Wu, the Gambling Cop

This job is where things shift. Tommy Wu is no ordinary debtor — he’s a cop, and a degenerate gambler with a dangerous habit. Roland sends Wei after him with a more delicate plan: target his wife.

Wei confronts her at the hospital, takes compromising photos, and uses them as blackmail. The goal is clear: emotional leverage. Tommy, stunned and cornered, quickly agrees to pay.

Though no physical harm is done, this mission hits a moral nerve. Using an innocent spouse as leverage blurs the line between enforcement and cruelty. For Wei, it’s a turning point.

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Full Circle: Samson Gao Returns

Samson Gao, from the first mission, resurfaces — deeper in debt and now hiding in Central. Roland wants to deal with him personally. What follows is a tense foot chase and a confrontation gone tragically wrong. Samson panics and dies trying to escape, plunging to his death.

The mission ends with Roland instructing Wei to visit the man’s widow and check for life insurance — a final straw for Wei, who’s visibly shaken. “When innocent guys start dying, that’s it for me,” he declares.

Roland, ever cold and calculating, sees no innocence in a man who owed him $20,000. But Wei has had enough. The line has been crossed.

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Final Thoughts: Morality and Consequence

The Roland Ho missions aren’t just side jobs — they’re a character study. They chart Wei’s descent into the role of enforcer and his eventual realization of where that path leads. What starts with intimidation ends in tragedy, offering one of Sleeping Dogs’ strongest examples of moral conflict within its open world.

As you play through these missions, notice how the tone shifts — from cheeky strong-arming to ethically fraught decisions. It’s one of the rare side arcs in gaming where the character grows during a favor chain.

By the end, it’s not about the money. It’s about what kind of man Wei wants to be — and what kind of city Hong Kong is turning him into.

If you’re chasing 100% completion or just following Wei’s personal evolution, this mission chain is unmissable. It’s one of Sleeping Dogs at its best: gritty, smart, and never morally simple.