Clarence Darrow

In 1887 Darrow made the move from Ashtabula to Chicago. He struck up an immediate friendship with Altgeld who guided his new protégé's career until Darrow became the general attorney to the Chicago and Northwestern Railroad in 1891. Darrow resigned his railroad position in 1894 to defend Eugene V. Debs (1855–1926), a labor leader charged with crimes related to a strike against the Pullman Company.

The trial marked the beginning of a series of criminal cases in which Darrow defended organized labor throughout the United States. This phase of his career ended in 1911 when Darrow himself was prosecuted for jury tampering in a Los Angeles, California, murder case. After two trials against him, the prosecution ended with a hung jury (a jury unable to reach a verdict). Though Darrow was not convicted, he was not acquitted either and his reputation was severely damaged. He never worked on behalf of organized labor again. He returned to Chicago with his finances in ruin, trying to make a living in criminal defense work and rebuild his law practice.