They’d known each other for two decades, the New York real estate mogul and the Canadian British owner of a transatlantic newspaper empire, working together as business partners on a Chicago skyscraper project.
Trump returned the favor, at times. He once called Black “a tremendously strong man.” But in 2007, when Black was on trial for ripping off his own company, Trump was asked in a radio interview whether Black was his friend.
“I just have to see,” Trump replied.
On Wednesday, President Trump granted Black a pardon, wiping clean the fraud and obstruction-of-justice convictions for which the former owner of the Chicago Sun-Times served three years and two weeks in prison.
Earlier this month, when Trump called Black to inform him of the decision, the two men, both objects of federal investigations for many years, bonded over their mutual loathing of prosecutors they view as overzealous.
“I suggested that he knew ‘better than anyone’ the antics of some U.S. prosecutors,” Black wrote in his account of Trump’s call in the National Post, a Toronto-based paper.
According to Black, Trump noted that they had “known each other a long time” but said “that wasn’t any part of the reason” for the pardon. Nor, the president said, was the pardon a reward for all the nice things Black has said and written about Trump.
In a statement announcing the pardon, White House press secretary Sarah Sanders praised Black as “an entrepreneur and scholar [who] has made tremendous contributions to business, as well as to political and historical thought.”
Whatever the president’s motivation, Black was effusively grateful. He had applied for a pardon from President George W. Bush, to no avail. He had good cause to hope his chances would be better with Trump.
The president has now pardoned 10 people, most of them conservative political figures or people who have supported or praised Trump. This week, in addition to Black, Trump pardoned Patrick Nolan, the Republican former leader of California’s State Assembly and a friend of the president’s son-in-law, Jared Kushner. Nolan was convicted of racketeering after the FBI videotaped him accepting checks to support a bill to help a fictitious company open a shrimp processing plant.
The chairman of the House Intelligence Committee, Rep. Adam B. Schiff (D-Calif.), on Thursday said he will introduce a bill to give Congress access to investigative records about any figures in the federal investigation of Trump’s activities whom the president pardons. Schiff said the measure seeks to prevent the president from using pardons “to cover up crimes.”
Black, 74, has been a fan of Trump for many years. In one of his books, Black listed Trump along with Carl Icahn and Kirk Kerkorian as one of the rare American business moguls who were “buccaneers” brave enough to admit to being capitalists.
For many years, they were neighbors along Palm Beach’s row of oceanfront estates. Black met with Trump often at Mar-a-Lago, the president’s club there. Black was a guest at Trump’s last wedding, and Trump went to a birthday party for Black’s wife.
They found they had much in common.
They share a talent for winning attention by deploying an acid tongue. During his trial in 2007, Black referred to the government’s lawyers as “Nazis.” On Wednesday, after his pardon was announced, Black attacked the judge who put him in prison as “self-serving” and declared that the whole case against him had been “nonsense, all of it,” a miscarriage of justice in “the conviction-mad United States.”
Like Trump, Black is a colorful character who enjoys showing his wealth — both men have owned private jets and multiple homes — and relished being politically incorrect. He was not eligible to serve his time in a minimum-security setting for white-collar criminals, so while he was imprisoned in a general-population facility, he quipped that he was “one more unjustly imprisoned Black man.”
And like Trump, Black savors support from boldface names. Elton John wrote a letter lobbying for Black’s pardon, just as he had written a character reference for Black during the 2007 trial.
Trump and Black also both have a distinctive way of minimizing actions that others might find offensive or outrageous. Black on Wednesday described his own actions in the case that led to his conviction like so: “It came to light that some payments from our American to our Canadian company and to certain executives, including me . . . had not been fully authorized.”
The scheme worked like this: Black was chief executive of Hollinger International, a company that owned newspapers, including the Sun-Times. When Hollinger started selling off many of its small papers, in 1998, Black and his fellow defendants, without permission from their company’s board, paid themselves millions in “phony management fees” for promising “not to compete with a company they themselves owned,” as then-Solicitor General Elena Kagan put it.
Appellate judge Richard Posner described it as “pretty naked fraud.”
After Black learned that federal authorities had launched a fraud investigation, he “removed 13 boxes of documents from his office,” an act that was caught by parking-garage video cameras, Kagan wrote in the government’s brief.
As the White House statement recounted it Wednesday, prosecutors alleged that Black “committed several acts of mail fraud and obstruction” but the Supreme Court “largely disagreed and overturned almost all charges in his case.”
In fact, in a unanimous decision delivered by Justice Ruth Bader Ginsburg in 2010, the Supreme Court threw out Black’s conviction on two fraud charges because the jury had been given unclear instructions, but it left untouched his conviction for obstruction of justice.
The case was sent back to the lower court to be reconsidered, Black’s convictions on two counts were upheld, and he was returned to prison.
Black and Trump also share a penchant for pushing back aggressively against those who criticize them — and lavishly praising those who support them.
Trump sued one of his biographers, Timothy O’Brien, for $5 billion in a libel suit that was eventually found to be meritless, but he also has a long history of showering praise on writers who publish glowing reports about his success.
Black has given the president plenty of reason to see him as one of those writers. Last year, he published a sparklingly upbeat biography titled “Donald J. Trump: A President Like No Other.”
“He is not, in fact, a racist, sexist, warmonger, hothead, promoter of violence, or a foreign or domestic economic warrior,” Black wrote. He wrote that Trump is “not a liar as much as a disbeliever in absolute secular truths. . . . For Trump, establishing the facts of a matter is as much a competition as anything else.”
Beginning in 2001, Trump and Black became business partners. Trump wanted to build a 92-story residential and commercial skyscraper on the site of the Sun-Times’s riverfront headquarters. Originally, the two were equal partners in the deal, but after Black got into legal hot water, Trump took full control of the property.
From the start, Black has written, directors of his company warned him to be cautious about dealing with Trump, to “keep my hand on the company’s wallet, that Trump was a scoundrel who could not be relied on for anything.” But Black said Trump “came in on budget all the way through” and “delivered exactly what he had promised under our contract.”
“I found Trump a good deal more ethical and honest than many other businessmen,” Black wrote.
On the day before he was pardoned, Black, who now calls himself a historian and “justice reform advocate,” published an article in the National Review headlined “Smooth Sailing Ahead for Trump.”
The story predicts a clear path to a reelection victory for the president: “The times are good and his opponents are not. . . . Barring something completely unforeseeable, this president will have a stronger argument for reelection next year than any president since Richard Nixon in 1972 after his extraordinarily successful first term.”