|Act||Act II - Interlude|
Sly makes his debut after Buffalo, Hermit's second bodyguard, is defeated. He offers to reveal Hermit's secret power to Shadow for 450 Coins. If the players accept his offer, he takes the money and disappears without divulging the said information.
Sly appears again during Act III. He blames Shadow because after the fight between Shadow and Hermit, everyone knows his secret power and he cannot deceive people anymore, which implies that Shadow is not the first person he was trying to trick. Sly rejoins Shadow and his companions at the end of Act III when they catch up to him as he is about to leave on a boat.
Upon reaching Act IV, Sly explains to the group that the harbor was governed by the Pirate King who disappeared a while back and that now his daughter Wasp has succeeded him. Many of her crews are displeased with this and decides to rebel against her by founding a group called "New Blood". Later, Bosun tells them that Sly had been taking advantage from the conflict by selling weapons to New Blood.
During Act V, upon encountering Widow, Sly is immediately bewitched by her and sets out to buy expensive gifts in order to impress her. Her hold over him is broken only after Shadow defeats her, for which Sly thanks him profusely.
During the events of Act VI, when shadow is mistaken for the Prince, it is Sly only who suggests that Shadow play along with the ruse.
Sly replaces May's role as Shadow's assistant during the Interlude after May is captured during the closing of the Gates of Shadows. Upon reaching the Interlude, Sly introduces the player with a new currency that is being used during the Interlude, Platinum. He also replaces Sensei's role in describing the rules from Challenges and Duels. At the end of the Interlude, Sly does not follow Shadow to enter the reopened Gates. He bids his farewell to Shadow, claiming that it was a honor to travel with him.
- You seem like a smart fighter. Want a leg up in the competition? I know Hermit's secret. You can have it... for a price. - Talking to the player after defeating Buffalo
- Excellent doing business with you. You won't regret it. I'll be back in a bit for delivery. - After the player accepts Sly's offer
- Time is money, and you've just cost me both. Oh well, it's your loss. - After the player rejects Sly's offer
- Your fight with Hermit destroyed my business! Now everyone knows the secret.
- I'll have to think of a new plan... I'll have plenty of time for that. A ship awaits me. Farewell - After Rhino is defeated
- You again? What kind of trouble are you going to cause me this time? Well, I'll help you. Just this once! But I'm still angry. Cast off! - After Butcher is defeated
- Of course I've heard! Some time ago the Pirate King disappeared. His daughter, Wasp, took over and now controls this harbor.
- It's said Wasp has a magic amulet which brings luck to its owner... - Explaining their destination to Sensei
- Getting to Wasp won't be easy. She's had some trouble recently and has gone into hiding. Anyway, not my problem. A job awaits! Good luck! - After reaching the harbor
- Ah, so you've met these "New Blood" fellas. Some of Wasp's crewmen mutinied and took over her ships.
- She's got a few loyal henchmen by her side, but they're still in hiding... oh, I should be going! - After Kraken is defeated
- I can explain everything! But now isn't the time... can you help a friend out here? - Before fighting Bosun
- I can't forget that beautiful woman! Her face is all I see when I close my eyes.
- I spent all my money on a gift for her - surely, these precious gems will tell her how I feel about her. - Sly talking to the player about Widow, after defeating bodyguard Irbis
- Am I all... No! No, I'm not all right! What's happening to me? This is maddening! - Sly falling in love with Widow
- I'm feeling a bit... dizzy. Widow's spell turned me into a weak-willed, love-sick maniac! Thanks for saving me. I owe you a big one. - After Widow is defeated
- Interesting... This fool seems to think you are some 'prince'. I think you should play along. - After Corporal is defeated
- Hey, don't look at me! I like you guys, but there is no profit in dying or becoming another shadow. Good luck though! - After the Gates of Shadows battle
- An unexpected turn of events... I'm truly sorry about your friend, Shadow.
- This was a bad idea from the start. But now, we must open the Gates once more to save May. Any ideas? - After May gets sucked inside the Gates of Shadows
- What? Are you serious?.. Oh, what am I saying - of course you're serious... Well, Lynx is first in line, so I guess we should start there. -Talking to Sensei about a plan to break the Seals
- I tried to get us some snacks, but they threw my money back in my face! It appears that platinum coins are in use now.
- However, I did manage to find some local simpletons to exchange our gold for the new coins at a favorable rate! Sometimes I amaze even myself... - Talking to the player after the currency change
- Now that they're taken care of, what's next - After all demons are defeated in Interlude
- This is suicide. I know May is your friend... but do you really want to do this? - At the end of Interlude
- No matter what happens, it was an honor to travel with you, Shadow. - Sly's last words to Shadow
- His name is descriptive of his cunning and deceitful personality. However, although he starts out with the intent of tricking Shadow and company, by the end of their adventure he becomes a friend to them.
- During Christmas 2016 update, Sly is attacked by Freeze when he is looting for something in Underworld. He is later found by Volcano and Vortex.