Leaving the area in disgrace, she ventured to the waterfront area in West Side Manhattan. It was while wandering the dockyards in the spring of 1869 that she witnessed members of the Charlton Street Gang unsuccessfully attempting to board a small sloop anchored in mid-river. Watching the men being driven back across the river by a handful of the ship's crew, she offered her services to the men and became the gang's leader. Within days, she engineered the successful hijacking of a larger sloop and, with "the Jolly Roger flying from the masthead", she and her crew sailed up and down the Hudson and Harlem Rivers raiding small villages, robbing farm houses and riverside mansions and occasionally kidnapping men, woman and children for ransom. Sadie was even said to have made several male prisoners "walk the plank".
Sadie and her men continued their activities for several months and stashed their cargo in several hiding spots until they could be gradually disposed of though fences and junk shops along the Hudson and East Rivers. By the end of the summer however, farmers had begun resisting against the raids by attacking landing parties with gunfire. The group eventually abandoned their sloop and Sadie returned to the Fourth Ward, where she was now known as the "Queen of the Waterfront", and she made a truce with her old rival Gallus Mag. Her ear was later returned to her by Gallus Mag, who displayed it in a pickled jar at her bar; Sadie afterward kept it in a locket and wore around her neck for the rest of her life.
Sadie is referenced in several historical novels, most notably, J. T. Edson's Law of the Gun (1968), Tom Murphy's Lily Cigar (1979), Bart Sheldon's Ruby Sweetwater and the Ringo Kid (1981) and Thomas J. Fleming's A Passionate Girl (2003).
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