IF YOU HAD TO SUFFER THE INDIGNITY of house arrest, you could do a lot worse than Conrad Black’s estate at 1930 South Ocean Boulevard in Palm Beach, Florida. The sprawling 21,000–square–foot British Colonial-style residence sits on one of the most privileged stretches of real estate in the United States, with the Atlantic Ocean bordering one side of the property and the dark blue waters of Lake Worth lapping at the other. While awaiting his November 30 sentencing in Chicago—where the 63–year–old former chairman of Hollinger International faces up to 35 years in a federal prison—Black could play tennis on his private court, enjoy a refreshing dip in the pool, screen his favorite movie in the home theater, or reenact his own version of The Great Escape through the tunnel connecting his property to a 300–foot stretch of private beachfront. The only physical reminders of the newspaper baron’s impending incarceration are the black iron bars that encircle the property to keep out those who want to catch a glimpse of corporate America’s latest celebrity convict.

But while other fallen chieftains spend their final days of freedom gorging themselves on the vestiges of ill–gotten gains before the feds move in—picture the bloated, alcohol–tinged countenance of ex–Enron honcho Jeffrey Skilling—Black remains characteristically sanguine, ever the battle–tested general counting his casualties and awaiting reinforcements before launching his next attack. “It has been a four–year battle, and after the opening assault that I had pillaged the company for hundreds of millions of dollars, and the prolonged effort to impoverish me and imprison me for life, I feel I have steadily gained ground, and have an excellent basis for appeal,” Black wrote to me in his first interview since a Chicago jury found him guilty of three counts of mail fraud and one count of obstruction of justice. “Being a historian, I am fairly familiar with the ups and downs of people’s careers and may be able to assimilate a cataract of horrors better than some people.” I had e–mailed him a long list of questions in August (on his lawyers’ advice, he consented only to a written exchange, with his responses vetted by his legal team) about his thoughts on his criminal trial, his state of mind as he prepares for a lengthy prison sentence, and his feelings about his fallen media empire. Three days later, I received a 1,400–word response that was candid, thoughtful, and wholly unapologetic. Written in the bombastic, abstruse style for which he is famous, Black’s statement displayed the fierce intellect responsible for his extraordinary rise—but also suggested the qualities responsible for his sudden, devastating fall.

Black’s conviction ended a long saga at the company he cofounded in 1969 with the purchase of a small Quebec paper and transformed into the third–largest newspaper empire on the planet, with more than 500 papers including The Telegraphof London, the Chicago Sun–Times, and Canada’s National Post. It all began more than four years ago, when a special committee appointed by Hollinger International’s board of directors—headed by former SEC chairman Richard Breeden—accused Black and several of his associates of running a “corporate kleptocracy” that siphoned $400 million from shareholders. It continued when a grand jury corralled by U.S. Attorney Patrick Fitzgerald—the überprosecutor who scored a conviction against Lewis “Scooter” Libby—indicted Black on 14 counts of criminal fraud: racketeering, obstruction of justice, money–laundering, and mail and wire fraud. And it culminated on July 13 when the jury found him guilty on four of those counts.

From the moment he was accused, Black has couched his predicament in militaristic terms. A history buff since childhood who can recite from memory, say, the main armament of a World War II battleship or the daily casualty reports during Hitler’s siege of Stalingrad, Black portrays himself as the victim of a malicious witch hunt; at one point during the trial he even called the prosecution Nazis. It’s clear that his conviction has not tempered his views. “We have the…pursuit of prominent, well–off people who get into the crosshairs of the system essentially as a substitute for a wealth–redistribution policy, and we have a certain revulsion against extreme proliferations of wealth,” he wrote to me. “Property is seized without compensation, due process has eroded, and the grand jury is no protection at all against capricious prosecutions. It is a difficult time to be a corporate defendant.”

Indeed, Black’s was the last in a series of prominent corporate trials—Enron, Tyco, WorldCom—that defined an era of unprecedented shareholder activism in American business. Like Dennis Kozlowski at Tyco and the Rigas family of Adelphia, Black was convicted of running the publicly traded Hollinger like his own private smoke shop, helping himself to the till—and the pockets of shareholders—whenever he needed spare change. But like Martha Stewart, Black’s renown transcended the boardroom. In Britain, where he holds a seat in the House of Lords, he is Lord Black of Crossharbour, the former proprietor of the most popular conservative broadsheet in the country. And in Canada, where he was born and where he began his meteoric rise, he is, as the director of the documentary Citizen Black put it, “our own Charles Foster Kane.”

Black’s trademark blend of glamour, erudition, and audacity are best captured in a photograph of him, taken at Kensington Palace in the summer of 2000, dressed in the crimson vestments and matching four–cornered hat of Cardinal de Richelieu, the 17th–century French prelate and Chief Minister to King Louis XIII. A self–described Francophile who reveres Napoleon and de Gaulle, Black is also a convert from Anglicanism to Catholicism (at age 41) who famously built a private chapel—consecrated by two cardinals—on the grounds of his home in Toronto, where he grew up a member of the city’s moneyed elite. He no doubt identified with Richelieu’s reputation as one of history’s true Renaissance men: a nobleman, clergyman, statesman, author, and patron of the arts. Standing by Black’s side, his wife, Barbara Amiel, makes a fetching modern–day Marie Antoinette, her bounteous décolletage heaving beneath demure white lace.

As Black awaits his sentencing in Palm Beach—the judge forced him to surrender his passport and remain there or in Chicago—he says his faith provides some comfort. “It has been helpful…in reading apposite passages from ecclesiastical authors, especially Cardinal Newman, and in conversation with several very knowledgeable clergymen.” Every evening, if the weather permits, he sits on his terrace and enjoys a glass or two of good French wine. “It is a terrible thing to be wrongly accused, and assaulted and defamed,” he wrote me. “And it is even more terrible to be unjustly convicted…[But] my health is good and I will survive it all.”

The trial of United States v. Conrad Black et al. began on March 19, 2007. But for Black’s defense team, the true showdown came nearly two months later—the day Hollinger International’s former president David Radler took the stand to testify against his friend and business partner of 35 years. “The government has based its case against Conrad on David Radler,” Black’s attorney Eddie Greenspan—a heavyset 63–year–old with a full head of well–coiffed white hair and a reputation as the Canuck Johnnie Cochran—would say during his closing argument. “The government, at the very beginning of the trial, admitted its star witness is a liar. But [the prosecution] told you that David Radler’s testimony would be supported by other witnesses and by documents. Well, they were at least right about one thing: David Radler is a liar.”

On the morning of May 8, Radler—a trim sexagenarian with a receding hairline and large glasses perched on his prominent nose—shuffled self–consciously into Courtroom 1241 of the Everett McKinley Dirksen building. To reach the witness box at the back of the room, he had to walk through eight rows of church pew-style wooden benches, packed with reporters who had traveled from across the U.S., Canada, and Britain to cover what the Canadian newsmagazine Maclean’s billed as “The White–Collar Trial of the Century.” In front of Radler, two large rectangular tables had been arranged to accommodate Black, his co–defendants (Mark Kipnis, John Boultbee, and Peter Atkinson), and their respective teams of attorneys and laptops, giving the room the appearance of a trading floor at a brokerage house rather than the setup familiar to viewers of Law & Order. The four principal members of Fitzgerald’s prosecution team huddled around a third table, which was so close to the jury box that prosecutors could smell who had eaten garlic on their lunch break. During nearly two weeks inside the witness box, Radler had to pass within a foot of his ex–friend and colleague. But Black steadfastly avoided his gaze.

In fact, the longtime associates were a study in contrasts. Radler slouched forward when he walked, his head darting furtively from side to side, while Black had a stiff, almost regal bearing. Radler sported bright pink or orange ties with his white shirts and dark suits, whereas Black wore the subdued blues and grays of a London banker. Radler’s face was deeply tanned, as though he had just returned from a trip to Tahiti; Black, we learned during testimony about a Hollinger–financed jaunt to Bora–Bora, was not a fan of the tropics, and his chalky gray complexion betrayed years spent writing and pontificating into the early hours of the morning (he once e–mailed me at 4:22 A.M.).

In order to fully grasp the case against Black it is important to understand the convoluted corporate structure through which he controlled Hollinger International—a series of interconnected private companies that resembled a set of nested Russian matryoshka dolls. In the center was Ravelston, a private Toronto holding company owned by Black and Radler, which owned another privately held Toronto holding company, Hollinger Inc., which in turn controlled a majority of the publicly listed Hollinger International. In an ingenious arrangement, Ravelston collected “management fees” from Hollinger International, essentially an outsourcing fee for the use of Ravelston’s executives. The same team already collected generous compensation from Hollinger International, meaning Black and the others got paid twice for the same job: a salary from International and a management fee through Ravelston. Although Black and his co–defendants weren’t charged criminally for it, the double–dipping formed the basis for the investigation by the Special Committee—and ultimately led to Black’s indictment.

Lead prosecutor Eric Sussman—a lithe, 38–year–old marathon runner with boundless energy who presented a marked contrast to Black’s ponderous, aging defense team—began by taking Radler through his long history with Black in order to portray them as inseparable colleagues and friends. How the two men—Radler, the son of a restaurateur, and Black, the son of a wealthy brewery executive—had met in Montreal in 1969 and together made an $18,000 investment in a community newspaper, the Sherbrooke Record. How they drastically cut costs and increased profitability, selling the paper in 1977 for a whopping $865,000, and plowed the profits into another paper, and then another. Sussman then outlined a central charge of the government’s case: That during a sell–off of most of Hollinger International’s newspapers between 1999 and 2001, Black and his co–defendants schemed to divert more than $60 million that rightfully should have gone to the public shareholders of Hollinger International.

The details are mind–numbing, but basically they involve a standard business tool in the newspaper world: the noncompete agreements guaranteeing a paper’s seller that the buyer will not simply start up a new rag, poach the best staff, and reenter the marketplace. The prosecution charged that Black, Radler, and the others inserted themselves and Hollinger Inc. as beneficiaries in several of the noncompete agreements, personally claiming a large chunk of the proceeds of these sales and thus defrauding the shareholders of Hollinger International. (There is nothing criminal per se about an executive at a public company signing an individual noncompetition agreement as long as 1. the company’s board of directors and auditors approve it and 2. it is disclosed to shareholders—the latter of which, in the jury’s mind, Black failed to do.) “The payments were approved as management fees and again as noncompetes,” Black insisted to me. “I do not think they were illegal. I don’t think any serious doubt about my business acumen was raised in this case.”

On the stand, Radler blamed it all on Black: “He suggested that we insert ourselves in the noncompete process and I agreed.” While Radler’s story may have been straightforward, his delivery was anything but. Nicknamed “Ratler” by the media for his willingness to testify against his former partner, the government’s star witness often seemed to have a frog in his throat. Under cross–examination, Radler at first appeared shaken by Greenspan’s aggressiveness:
Greenspan: Was it easy for you to lie? Did you stutter before you lied? Was there a long pause before you lied? Did you avert your eyes?
Radler: Sir, I told lies.
Greenspan: I take it we could be talking to you right now and you might be lying, true?
Radler: False.
Greenspan: False? I have your word on it?
Radler: Yes, you have my word.

But Radler recovered as the cross–examination continued, parrying Greenspan’s barely controlled fury with dry wit. In one memorable exchange, Greenspan asked him about the time—shortly after they acquired the Sherbrooke Record—the U.S. Congressional Record selected an article Black had written about LBJ.
Greenspan: That was a very big deal in Sherbrooke?
Radler: I don’t remember that.
Greenspan: Having an article from Sherbrooke, Quebec, read into the Congressional Record wasn’t a big deal?
Radler: It was certainly a big deal for Conrad.

As the details of his life and alleged criminal acts emerged in open court, Black looked on with an expression of studied disinterest. When something caught his attention, he would lean over to whisper in Greenspan’s ear. Occasionally, his eyes would wander over to the press—many of whom had worked for him directly or indirectly—or settle on the jury of nine women and three men who would decide his fate. Juror Jean Kelly, a 51–year–old mail carrier from the suburb of Crest Hill, was unnerved by Black’s gaze. “He had a tendency to look down at us, like he couldn’t believe people so beneath him were responsible for his freedom,” she told me recently. “He didn’t portray any warmth, any emotions at all. It looked like he thought the whole trial was a big waste of his time.”

During breaks in the action, Black often huddled with his wife and grown children from his first marriage, who were seated in the front pew just behind the defense team. (Staunchly supportive of her husband, Amiel had her own run–ins with journalists during the trial, calling some of them “sluts” and “vermin.”) Black’s sons, James and Jonathan, made occasional cameos, and his daughter, Alana—a tall, striking 25–year–old who looked like she had just stepped out of the pages of a fashion magazine—was a daily fixture. But for a noted raconteur used to commanding every room he enters, Black’s forced silence as witness after witness attacked him seemed to drain his magnetism, leaving him vulnerable at the end of each day to the throng of reporters and TV cameras outside the courthouse. When I asked him whether he would have liked to take the stand in his own defense, Black wrote, “My testifying would have opened the trial up to a much wider range of questions, which I could have dealt with, but it would have made the trial longer and more complicated.”

In their unrelenting focus on destroying Radler, the defense made a fatal error: They failed to convince the jury that Black and the other co–defendants were legally entitled to the millions of dollars in noncompete money that flowed to them directly—or indirectly, through Black’s private holding company, Hollinger Inc.—from the newspaper sell–offs. Early in the trial, several buyers testified that they had not requested noncompetition agreements from anyone other than the publicly held Hollinger International—leading the jury to conclude that Black and his cohorts did not deserve the additional proceeds from these sales. “We did not consider these people to be potential competitors in these small towns,” Michael Reed of Community Newspaper Holdings Inc. of Birmingham, Alabama, testified in a particularly damning moment. The buyers also established a pattern of dubious behavior at Hollinger—including a $5.5 million noncompete fee paid to Hollinger Inc. from one of Hollinger’s own subsidiaries, American Publishing. Black’s defense team claimed the deal was meant to ensure that Black and the others wouldn’t compete with American Publishing should they leave the company. But at the time of the deal, American Publishing owned just one small paper in Mammoth Lakes, California.

Allegedly turning a blind eye was Hollinger’s star–studded audit committee—responsible for approving all executive compensation—composed of Marie–Josée Kravis, a noted conservative economist, president of MoMA, and spouse of private equity titan Henry Kravis; James Thompson, a former U.S. attorney and four–term governor of Illinois; and Richard Burt, a former U.S. ambassador to Germany. The committee contributed some of the trial’s more far–fetched moments, repeatedly insisting on the witness stand that they had missed every single reference to the noncompetes when approving Hollinger’s financial statements. In his closing statement, Greenspan argued: “These three individuals, knowing full well their responsibilities as members of the audit committee, want you to believe that they missed this disclosure…a collective total of 33 times?” The prominence of Hollinger’s directors—other board members had included Henry Kissinger and Richard Perle—has always been a source of pride for Black, and even now, he tries to put a positive spin on their betrayal. “The jury clearly determined that all of the former Hollinger directors who testified lied under oath, and they did,” he wrote to me. “None of them would have wished to lie, but all appeared with an official rod on their backs, immunity or a plea bargain.”

Whether or not this is true, the defense also failed to counter the only real smoking gun—surveillance videotape that showed Black personally removing boxes from Hollinger Inc.’s Toronto offices in apparent violation of an SEC order, which resulted in his conviction for obstruction of justice. For effect, the prosecution subpoenaed the 13 boxes—containing Black’s files and personal belongings—from Canada and had them brought into the courtroom, where they stayed in view of the jury for several days. When Greenspan called Black’s secretary, Joan Maida, to testify about the incident, she proved to be the worst witness of the entire trial, transforming what could have been a simple explanation—that Black had to remove his personal effects after being dismissed as chairman—into a dubious one by repeatedly changing her story about how many boxes she packed. “I knew nothing of any official interest in the famous 13 boxes, had nothing to do with selecting their contents,” Black wrote to me. “I did not alter or even examine the boxes when they were in my house. Doubtless, this could have been better explained.”

Indeed, Black’s vaunted legal team drew mixed reviews for their performance. Greenspan was trying his first case ever in the U.S., which resulted early on in a series of embarrassing gaffes. And his vicious treatment of Radler alienated the jury, undermining his effectiveness in other areas of the case. “I was offended by Greenspan,” Kelly says. “When Radler was on the stand, he was screaming at us, telling us what we were supposed to think. We walked out of there every day with stomachaches.” And cocounsel Eddie Genson, a famed Chicago trial lawyer who suffers from a neuromuscular condition that relegates him to a motorized scooter or crutches, often seemed lost. “I felt sorry for him,” says Kelly. “I heard he used to be a great attorney, but he should have been put out to pasture a long time ago.”

Throughout, the prosecution put Black’s lifestyle on trial, including perks like his $5 million corporate apartment in New York, Amiel’s sixtieth birthday party at four–star Manhattan restaurant La Grenouille—a $62,000 extravaganza largely paid for by Hollinger International—and the company jet, which shuttled him between luxurious homes in London, Toronto, and Palm Beach. This strategy had backfired in the case of Dennis Kozlowski and his infamous $6,000 shower curtain, and the prosecution was mindful of not distracting the jury from the core charges. “They made a conscious effort not to overplay the perks,” says a source close to the prosecution. “But they would do it again in a heartbeat because it gave the jury insight into how Black treated his company’s money.”

The Blacks were certainly an easy target. Black’s exalted position as the proprietor of The Telegraph attracted a social set that included Margaret Thatcher and Lord Carrington, the former secretary–general of NATO who in 2001 secured Black the seat in the House of Lords that he had openly coveted for years. (After a public spat with then Canadian prime minister Jean Chrétien, Black was forced to give up his Canadian citizenship to accept the honor.) Black’s defense team was obviously concerned that their client’s wealth would turn off the jury, and tried to draw a distinction between fortune and fraud. “Ladies and gentlemen, Conrad is different…from you and me. He is a rich man,” Greenspan said during his persuasive closing argument. “But in America, you do not convict people for being rich. Ask yourself: Why are the prosecutors focusing on this? Because they hope you will judge Conrad Black not on the facts of this case, but on his wealth, his lifestyle, and his vocabulary.”

Although the jury acquitted Black on all the so–called lifestyle counts, evidently they never believed that a man who spent his life being chauffeured around in limousines and waited on by servants would lug his own boxes—unless he had something to hide. And when the two–week deliberations began, nine of the twelve jurors wanted to convict Black on all counts. “A lot of people may have been swayed with the talk about his $4,000 towel–warming bars, and they were angry about what he had done to the shareholders,” Kelly told me. “They said, ‘He’s arrogant, we have to nail him on something.’” But the three holdouts pushed them to examine the counts one by one and convict based on evidence rather than emotion. “I don’t think anyone realizes just how close Black came to being found guilty on everything,” Kelly says.

On November 30, Conrad Black will finally have to face the enormity of his fate. He could spend the rest of his life in a federal prison, although experts predict that Judge Amy St. Eve will probably give him between seven and fifteen years. The company he built into a media behemoth, Hollinger International, has changed its name to the Sun–Times Media Group and is now run by Cyrus Freidheim, a turnaround specialist who previously took the helm at Chiquita Brands following its bankruptcy. Meanwhile, Black faces a mountain of civil suits—from the SEC, the Ontario Securities Commission, and Sun–Times Media, which is suing him and other former executives for $542 million—that could bankrupt him and keep him in court for the rest of his days. Most of his personal wealth, once reported at $400 million, came from Hollinger shares and stock options—neither of which are much good to him now. The majority of his remaining assets are in real estate, but those properties have been seized or diminished in value by large mortgages, tax liens, or bail bonds. He is also currently waging a battle to keep his $35 million Palm Beach house, which he used as collateral to secure his $21 million bail, though the government has argued in court that it should be seized as “forfeiture”—the spoils of his criminal acts. While it’s impossible to say exactly how much of his fortune remains, it is likely not enough for a man who once famously claimed that “greed has been severely underestimated and denigrated.”

Although old friends like author George Jonas and Canadian news broadcaster Brian Stewart have stuck by his side, Black’s dance card is lonelier these days. “This experience tends to reduce social activity, not so much because of fewer invitations, though there is some of that, but because it has been such an ordeal, anyone would naturally be less sociable,” he wrote me. “And the subject of these travails becomes an 800–pound gorilla nobody mentions. We and other polite people don’t want to talk about it, but it is hard to ignore, and some awkwardness results.”

Characteristically, Black prefers to focus on his appeal rather than dwell on thoughts of detention. “I still hope for a complete acquittal,” he wrote, “and on a worst case, not a severe sentence.” He has hired noted appeals specialist Andrew Frey, who helped investment banker Frank Quattrone overturn his obstruction of justice and witness tampering convictions. Legal experts say Black’s chances of exoneration are slim, but some point to the government’s narrow margin of victory as cause for cautious optimism. “Fitzgerald did a masterful job in his press conference, spinning this like it was a complete and total no–hit shutout,” says Hugh Totten, a trial attorney at Perkins Coie in Chicago who regularly attended the trial as a legal analyst. “At the end of the day, Black was convicted of defrauding the company of $3.2 million, much less than [the] $60 million he was accused of—and a far cry from the ‘kleptocracy’ Breeden found in his report. That’s what I call winning a case just barely.”

So far the only real winner appears to be David Radler, who is likely to get less than 29 months in prison. As a Canadian citizen, he may end up spending less than six months in a country club for pleading guilty to the same crimes for which Black now faces up to 35 years in the U.S. Ironically, Black would have been eligible to serve time in Canada—where sentences for nonviolent crimes are much less severe—had he not given up that right for a seat in the House of Lords. “I do regret giving up my Canadian citizenship,” he acknowledged, “but I always said I would take it back.”

Meanwhile, Black remains focused on the larger war—the one for his place in history: “I am hopeful that I will win, sooner or later, the battle for my reputation. The other matters are secondary.” It is a reputation Black’s friends say is badly misunderstood. “There is a Stephen Colbert quality to Conrad,” says David Frum, a conservative author who grew up in Toronto and has known Black for many years. “He has a style of talking that is larger than life. But he is not bombastic. A lot of the comedy of knowing him is that he has created this persona and is playing it for laughs.”

History is littered with stories like Black’s—men who lost everything they had trying to reach for what they didn’t need. And given his obsession with history, it seems a sad cliché that he was destined to repeat it. He has even been compared to the subject of his latest biography, Richard Nixon—a man of great talent undone by even greater flaws—though he sees few parallels. “He was a president and a historic figure; I was just a somewhat prominent publisher,” Black wrote me. “There is a stronger case for charges of illegalities against Nixon than against me. Where there may be some comparison is in the virtues of fighting these crises through and never giving up.”

In the eyes of Black’s former school chum John Fraser, a prominent Canadian journalist who worked for him as the editor of Saturday Night, Black’s obsession with American presidents (he also wrote a well–received biography of FDR) is reflective of a larger obsession with America. “Throughout his life, Conrad so admired the United States—there was no country he was more desperate to be successful in,” says Fraser. “But he was terribly naive to think he could behave the same way in the U.S. as he did in Canada.” In Canada, Black was the ultimate insider who ended up an outsider—the Establishment Man who abandoned the Establishment for a peerage. Now he can only look out at the waters of the Atlantic toward Britain—the country he adopted to become a lord—wishing perhaps that he had remained at home.

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