Trude was one of the most noted attorneys of his time, working on a number of high-profile cases.
Civil defense work in libel and tort claims against newspapers After Medill left office as mayor and returned to his private-sector job of running the
Chicago Tribune, he frequently hired Trude for the next twenty-seven years to represent the newspaper's defense in
libel and
tort lawsuits. None of the cases in which Trude defended
Chicago Tribune saw plaintiffs recover
punitive damages from the newspaper, and nearly all of the verdicts found no guilt on the newspaper's part. In the 1889 divorce suit between
Michael Cassius McDonald and his wife Mary, Trude served as McDonald's solicitor while A.B. Jenks served as counsel. Trude was a counsel in many high-profile cases of litigation regarding the contesting of
wills. Burke was prosecuted by
Charles S. Deneen, the Republican
Cook County state's attorney. (who was the son of the late
Carter Harrison III, who Trude had also represented in matters) In March 1905, he was part of a team of lawyers that sought a change of venue for proceedings related to the fire. Dora McDonald, who was married to Chicago crime boss and political boss Michael Cassius McDonald, had killed Webster Guerin, a man with whom she had had a decade-long
sexual affair. This affair had begun when Guerin, fifteen years her junior, was only a thirteen-year-old high school student. Dora McDonald had suspected Guerin of seeing other women, He had stood by his wife, who told him she had only shot Guerin because she was being blackmailed. Ultimately, in January 1908, McDonald was acquitted after only five hours of deliberation by a jury.
Prosecution in the murder case against Patrick Eugene Prendergast and work in subsequent litigation After
the assassination of Chicago Mayor
Carter Harrison III, Trude was initially seen as a likely
front-runner to win the mayoralty as a potential candidate in the
1893 Chicago special mayoral election. Trude instead opted to prosecute the case against Harrison's assassin,
Patrick Eugene Prendergast. Trude served as the lead counsel prosecuting the state's case against Prendergast, doing so at the request of both the county government and the family of Harrison. This is arguably the most noted matter that Trude worked on. After this, a petition for a
writ of habeas corpus and a request for a
stay of execution were presented on Prendergast's behalf to Judge
Peter S. Grossup of the
United States District Court for the Northern District of Illinois. Strong arguments were made on Prendergast's behalf by his team of lawyers. However, hours before Prendergast's scheduled July 13, 1894 time of execution, the court issued a detailed opinion in which they refused to stop the execution. Prendergast was
hanged. Further legal actions were unsuccessfully attempted by Prendergast's lawyers in the hours between the opinion being issued and the execution being carried out. ==Tenure on the Chicago Board of education==