Winston

Winston is a sharp-suited operator in the criminal underworld of Depression Era New York. Working through intermediaries, he hires both the down-and-out Ben Reilly and a rival detective named Patrick Donegal to hunt down a missing man called Jimmy Addison, keeping his own name and his employer's at arm's length from the job.

Winston comes looking for answers, appearing at Ben's office to demand the missing man's whereabouts and growing impatient when Ben requests more money. He is careful and guarded, a middleman who answers to someone higher up, and it is only when Ben and Donegal follow him through the streets that the danger of the operation comes clear: Winston works for the crime lord Silvermane.

Winston serves as the trusted lieutenant in Silvermane's operation, the man the crime lord sends to handle the delicate work. When Silvermane sets a meeting with a new Canadian supplier at the docks, Winston urges caution given the recent attempt on his boss's life, insisting on going ahead first to make sure the ground is safe, and takes his orders to track down both the missing Flint Marko and the private investigator nosing into their affairs.

His search for Marko brings him to Flint's apartment, where he combs the rooms while Ben Reilly hides just out of sight.. in an impenetrable closet, slipping away again without finding the detective tucked in the closet. Later, at the docks, Winston inspects the incoming shipment himself and signals the all-clear, giving Silvermane the word to come down for the meeting.

Winston works to prove himself to Silvermane, seemingly stung by the sense that his boss does not fully trust him to root out the rat in the organization. He vows to find the traitor and put him in the ground, and when he crosses paths with Ben Reilly, he pays the detective to bring any findings to him first. What he does not know is that the bills he hands over carry Silvermane's mark, the very thread Ben will use to unravel him.

His diligence becomes his undoing. After watching Ben leave Vera Addison's hotel, Winston slaps the truth out of her and learns the detective paid her off, then seizes Ben and Cat at Pennsylvania Station and hauls them before Silvermane in the woods. There he lays out his case against Cat, presenting a marked thousand dollars as proof of her guilt. But the mark is Silvermane's own, taken from the crime lord's safe, and in an instant the accusation turns back on him. Winston protests that Ben framed him, but the words do not save him, and Silvermane shoots his lieutenant dead.