In 1962, DeStefano was arrested after he tried to represent Vito Zaccagonini in a forgery trial in Rockford, Illinois. He later demanded the names of all employees in the state's attorney's and sheriff's offices so that they could be called as witnesses at his subsequent trial. During another court date in Rockford, when he was serving as his own lawyer as was his practice, he confused everyone in the courtroom when he approached the jury and asked, "Have you ever seen an elephant?" Moments later, DeStefano suddenly changed his plea to guilty, telling the jury, "something had come to light that I had not known before." The jury found him guilty and fined him $100 for disorderly conduct.