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A native of Chicago America, he was wanted in the states for shooting three men, but escaped due to Political influence. Arriving in England, he got involved with famed counterfeiter Roger Presbury, following a dispute over a card game, Presbury tried to draw his gun on him but as an experienced gunman, Winter drew quicker and killed him. He was arrested and imprisoned for five years. After being released he returned planning to help himself to the forged notes Presbury made. As the greatest counterfeiter in England, no one could tell Presbury's works were fakes. However he found that a Nathaniel Garrideb had moved into Presbury's base since them.
As a collector and studier of archaeological matter, Nathaniel never left. As such Winters formulated a plan, pretending to be a Mr. John Garrideb. He claims that he is looking for two other men who share his surname, due to the fact an extremely wealthy American with the same name, who was a friend of his had decided to leave his entire estate of 5,000,000 dollars, to be shared by three men with the name of Garrideb. Excited by the prospect of what his share could be, Nathaniel contacted Sherlock Holmes to try and find another Garrideb.
Angered at this, Winter went to visit Holmes and related the story. However Holmes noted several inconsistencies in his story, and tested him by pretending to be a friend of the mayor from where Winter claimed he was from. Winter fell for his trap and claimed to have known of the man Holmes invented. Suspicious at his motives Holmes investigated by going to visit Nathaniel Garrideb.
They were interrupted by Winter bursting in, holding an advert from apparently another Garrideb, as this would make three he insisted that Nathaniel go visit him in Northern England. However Holmes and Watson noticed several American spellings in the so called advert and realized that it was Winter who planted it, now knowing that it was Nathaniel's home he was after. Holmes went to talk to Inspector Lestrade who informed him of Winter's true identity.
That night Winter broke into Nathaniel's home to find the printing press that Presbury had hidden in the cellar, however he was confronted by Holmes and Watson, both armed. Never the less Winter managed to fire a shot, hitting Watson. In a moment of fury, Holmes violently assaulted Winter with the butt of his gun. Thankfully Watson only had a flesh wound. Winter confirmed the rest of the story, and tried to bribe Holmes and Watson into letting him go. But they turned him in, and he was arrested for attempted murder.