It's a scenario few could even have imagined when Conrad Black was found guilty of fraud and obstruction of justice in a Chicago courtroom in 2007, one that was packed so full of worldwide media and spectators that a second overflow room was set up in the downtown courthouse.
Black, who has called Trump a friend, published a book past year praising him, titled "Donald J. Trump: A President Like No Other".
The pair has known each other for decades and Trump was once in business with Hollinger Inc. In 2015, Trump tweeted his thanks to Black for a previous bit of praise in print: "As one of the truly great intellects & my friend, I won't forget!" "Honored to be your friend".
The 74-year-old ex-media mogul - whose empire once included the Chicago Sun-Times and UK's Daily Telegraph - has made "tremendous contributions to business, as well as to political and historical thought", The White House said.
Black was born in Canada and is a British citizen.
"He could not have been more gracious and quickly got to his point: he was granting me a full pardon", wrote Black, who used much of the rest of the column to explain the case. "It was never anything but a smear job".
The jury had to consider 42 counts against him and his three co-defendants - John Boultbee, of Victoria, British Columbia, Canada, and Peter Atkinson, of Oakville, Ontario, who are both former Hollinger International vice presidents, and former corporate counsel Mark Kipnis, of Northbrook, Illinois - in a highly complex trial.
"Formerly the owner of the world's then-third largest newspaper, he is also the author of several notable biographies and works of history", the White House noted.
Two of his three fraud convictions were later voided, and his sentence was shortened.
"In light of these facts, Mr Black is entirely deserving of this Grant of Executive Clemency", the White House said.
"The Supreme Court of the United States, however, largely disagreed and overturned nearly all charges in his case".
Both men have been out of prison for several years.