Although Pullman dropped out of school at age 14, he eventually became one of Chicago's most influential and controversial figures. He arrived in Chicago in 1855 and discovered that Chicago streets were frequently filled with mud deep enough to drown a horse. He suggested that the houses be raised up and a new foundation built under them, a technique his father used to move homes during the widening of the Erie Canal. In 1857, with a couple of partners, Pullman proved his technique would work by raising an entire block of stores and office buildings. He used his money and success to develop a comfortable railroad sleeping car, the Pullman sleeper. The first one was finished in 1864. Although the sleeper cost more than five times the price of a regular railway car, by arranging to have the body of President Abraham Lincoln carried from Washington, D.C. to Springfield on a sleeper, he received national attention and the orders began to pour in. Pullman built a new plant on the shores of Lake Calumet, several miles from Chicago. It an effort to make it easier for his employees, he also built a town with its own shopping areas, theaters, parks, hotel and library for his employees. When business fell off in 1894, Pullman cut jobs, wages and working hours. His failure to lower rents, utility charges and products led his workers to the Pullman Strike, which was eventually broken up by federal troops sent in by President Grover Cleveland.
Loathing for Pullman remained, and when he died in 1897, he was buried in Graceland Cemetery inside a Pullman Sleeper, with steel rails criss-crossed on top of it. Several tons of cement were poured over the sleeper to ensure that his body would not be exhumed and desecrated.
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