Known as the “attorney for the damned”, in 1894 he defended the railway leader Eugene Debs for his part in the Pullman strike; although he lost, he earned a reputation for taking on controversial cases. This flair for controversy brought him to the verge of bankruptcy (1911), when he was tried, but acquitted, of conspiring to bribe jurors. He defended over 50 people charged with murder, but only once did he lose a client to the executioner. In 1925 he defended the evolutionist biology teacher in the Scopes Trial but lost the case.