Anthony “the Gentleman” Calloway

Anthony “the Gentleman” Calloway is an influential underworld figure operating out of the squalid, congested slums of the Beggar’s Nest district in Neverwinter. A tall half-orc characterized by a broken tusk and slicked-back receding hair, he carries himself with a distinct, rugged elegance, dressing in an unusual suit made of eel-skin or a similarly strange, exotic fabric. From his makeshift throne at the back of his local establishment, he commands a crew of smugglers, thieves, and informants who navigate both the streets of Neverwinter and the complex subterranean network below.

To those in the know, such as Lady Aribeth’s spymaster Lucian Nightshade, the Gentleman is a vital source of illicit intelligence, possessing secrets that bypass even the city’s official espionage networks. However, dealing with him requires extreme caution; as Nightshade famously warns, one should “trust him exactly as far as you can throw him.” Additionally, despite his prominent half-orc physiology, any associate wishing to keep their teeth intact is strongly advised to never call him “Tony Halftooth” or “Tony” to his face.

The Cha-Ching Casino

The headquarters of the Gentleman’s operations is the Cha-Ching (sometimes referred to as the Cha-Ching Club), a prominent casino located deep within the narrow, laundry-draped alleys of Beggar’s Nest. Though fronted by an advertising mural of a scantily clad woman letting coins spill into her hands, the interior functions as a highly active, straightforward gambling hall. Its influence is vast enough that off-duty town guards and local judges can regularly be seen drinking and betting at the tables in broad daylight. The security of the establishment is managed by local toughs, including the brawler Hope, who served as a bouncer to clear her personal debts, and a quiet halfling lieutenant who stands at the Gentleman’s side.

Sewer Operations & Patricius’s Fate

For years, the Gentleman’s crew enjoyed uncontested, silent movement throughout Neverwinter by utilizing the city’s extensive sewers. This access was secured through a lucrative, quiet arrangement with Patricius, the city’s Head of Sewers and Waterways. Patricius, plagued by a severe gambling problem, routinely paid off his towering debts to the casino by granting the Gentleman’s smugglers key access codes and entry points to the underground tunnels.

This arrangement was complicated when Patricius acquired a magical Ring of Control Water Elementals from a rogue wizard, which allowed him to power the city’s massive waterways for free, bypassing the need to pay labor forces. Shortly before Neverwinter locked down for its war preparations, Patricius vanished entirely alongside the ring. Lacking its magic, the sewer system’s water levels began to fluctuate violently, unleashing a dangerous, rushing force deep within the tunnels.

When a group of adventurers investigated the sewers on the Gentleman’s behalf, they discovered that Luskan pirates had infiltrated the tunnels, captured Patricius, and were using the magical ring to enslave a water elemental. Though the party defeated the pirates, Patricius was killed in the fray. The adventurers recovered the pale, opal-blue ring but chose to keep its power for themselves, concealing it within a bag of holding.

Deception and the Prison Proposition

Following the sewer skirmish, the party returned to the Cha-Ching and delivered Patricius’s corpse to the Gentleman, fabricating a story that Luskanites had killed the waterways head and stolen the ring before it could be recovered. Accepting this explanation, the Gentleman provided half of the promised gold reward. In lieu of his full dossier on the compromised members of the Neverwinter Council, he shared a partial lead: the name of Talis.

Talis is held in the high-security wing of Neverwinter’s Peninsula Prison. To secure the rest of the intelligence on the compromised council members, the Gentleman presented a new proposition: the party must infiltrate the prison to free Talis and his own imprisoned criminal associate, Polly. Cautious as ever, the Gentleman demanded an unbreakable oath from the party as collateral before they set out on this high-risk rescue mission.

The Standoff and the Bluffed Dossier

The fragile truce between the adventurers and the Gentleman came to a head when the party returned to the Cha-Ching to press for the identity of the council spy without fulfilling the jailbreak first. Slipping into the casino while the bouncer Hope was off-duty, they confronted Calloway at his throne. Farwald and Gilmore cornered the crime lord, leveraging a solution to his sewer-water issues while pointing out his severe lack of manpower due to wartime conscription.

Under intense intimidation, the Gentleman finally cracked and confessed his own deception: he did not actually possess a secret dossier detailing the compromised council members. He had bluffed about holding the spy’s identity to gain leverage over the party. He admitted that the only person who truly knows the identity of the mole is Talis himself. Having no direct influence inside the high-security Peninsula Prison, the Gentleman could offer nothing more than a map of the facility to assist the party in rescuing Talis and his associate, Polly.