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Thomas Nast achieved several significant milestones in his fight against Tammany Hall. First, he created a visual language through political cartoons that allowed illiterate citizens to understand the machine's corruption, famously prompting Boss Tweed to say his constituents couldn't help but see "them damned pictures." Second, Nast famously turned down a $500,000 bribe offered by the Tweed Ring to stop his drawings. His persistent work eventually turned public opinion against the organization and played a crucial role in Boss Tweed being sent to jail.