On this date in 1875, William “Boss” Tweed, former head of the Democratic machine in New York City, escaped from jail and fled to Cuba. Tweed was facing hard time for his role in fleecing New York taxpayers of millions of dollars (some estimates run as high as $200 million). Almost captured in Cuba, Tweed moved on to Spain. He was arrested there in 1876 by a police officer who reportedly recognized him from a political cartoon by Thomas Nast. He was returned to the United States by Spanish authorities. He died of pneumonia in the Ludlow Street Jail in 1878.