Conrad Black was hoping his legal victories in the Supreme Court and the Seventh District Court of Appeals would convince a federal judge that he had already spent enough time in prison.
Media mogul Conrad Black must report to prison on Sept. 6 to serve his remaining sentence for mail fraud.
A judge's sentencing order was released Monday, according to the Chicago Tribune. Black's sentence was reduced last month to 42 months in prison.
The 66-year-old Black had already served 29 months in a Florida Federal prison for a number of convictions, but he was freed after the U.S. Supreme Court ruled that the "theft of honest services" law under which he was partially convicted was unconstitutionally vague.
Arguing against his re-incarceration, Black's attorneys pointed to his time in prison where they say he was a teacher, tutor and mentor. Other reports say he treated his fellow inmates like servants.
Upon the reading of his sentence, Black's wife collapsed in her bench. She was revived by her family and escorted out of the courtroom by marshals.
Black glanced over his shoulder to see what was happening but did not go to her.
It is not known where Black will serve the rest of his sentence.