Jurors thought Hollinger's Mark Kipnis was a nice guy. But that didn't stop them from convicting him. David Hechler reports

The jury called him St Mark – an odd name for Mark Kipnis, the former vice president, corporate counsel and secretary of Hollinger International, considering these same jurors convicted him of a felony. But saint or sinner, no one disputes that the 60-year-old lawyer is a genuinely nice guy. After his conviction in Chicago federal court last summer (following a four-month trial), neighbours, co-workers, and clients sent letters to the judge praising a man who helped them do everything from sell a business to fix household disasters. Even the prosecutor arguing for a three-year prison term at Kipnis's December sentencing hearing felt obliged to remind the judge: "Mr Kipnis was not indicted because he was a bad person."

Kipnis certainly looked like a nice guy compared to the executives he worked for – and who were tried along with him. They paid themselves millions of dollars in bonuses that they – and Kipnis, as the chief in-house lawyer – failed to disclose properly to shareholders. Former Securities and Exchange Commission chairman Richard Breeden, hired in 2003 by a special committee of the board to conduct an internal investigation, called Hollinger's culture a "corporate kleptocracy." Yet, as the one defendant who made no money on these transactions – he had his hands full heading a tiny, overworked law department (total head count: three) – Kipnis was no more than a bit player. He was not one of the bigwigs who pocketed the cash. That role chiefly went to Conrad Black, the company's founder and CEO, whose outsize ego dominated the courtroom and the media circus that surrounded it. Black was the high-roller who recruited fellow celebrities such as Henry Kissinger to join Hollinger's board, and later cashed in his Canadian citizenship to become a British peer.

At the company's peak, after a decade of acquiring newspapers around the globe, Hollinger owned about 400 papers, including The Daily Telegraph, Chicago Sun-Times, The Jerusalem Post and scores of community papers across the US and Canada. Kipnis, his lawyers say, simply signed off on Black's deals. In fact, Kipnis's first-year base salary at Hollinger merely matched what he had been making at Holleb & Coff, the law firm where he had worked before his in-house misadventure – $225,000 (£114,000). It rose to $275,000 (£138,000) in 2003, the year he resigned. On top of that, he was paid bonuses that ranged from 30% to 40%, and twice he was paid special bonuses for his work on the newspaper sales – $100,000 (£50,500) in 2000 and $50,000 (£25,000) in 2003. Prosecutors tried to paint these as payoffs for Kipnis's cooperation in facilitating the fraud. "His price was just a little bit lower," a prosecutor said in his opening statement. But Hollinger president F David Radler (who flipped and pleaded guilty) testified that the bonuses were legitimate, and the prosecution's argument failed to convince the judge or the jury.

Kipnis also differs from many of the other corporate counsel who have been indicted in recent years. Most lawyers swept up in accounting scandals or stock option schemes profited personally. William Sorin, former GC of Comverse Technology, pleaded guilty to criminal conspiracy in backdating company stock options that netted him more than $1m (£505,000). The ex-GC of Symbol Technologies, Leonard Goldner, pleaded guilty to stealing twice as much when he helped executives cook his company's books. And Hollinger executive vice president Peter Atkinson, a lawyer based in Toronto who actually hired Kipnis, was also convicted of sharing the loot.

In the end, Mark Kipnis was convicted for failing to challenge his bosses, who disguised some bonuses as non-compete agreements, and for failing, as corporate secretary, to ensure that the full nature of the payments was disclosed to Hollinger's audit committee and shareholders.

Was he put on trial just because he is a lawyer? "All of us have choices," says prosecutor Julie Ruder, sitting in a conference room in the downtown Chicago federal building where the trial was held. "None of this would have happened," Ruder says, referring to the fraud, "if Kipnis had made different choices."

Sitting next to her is Eric Sussman, another member of the four-lawyer prosecution team. "All Kipnis had to do," he says, picking up the thread, "was say: 'No, I don't feel comfortable with this. I'm not doing it'." Sussman does not think in-house lawyers are at greater risk these days, but he has seen one change: "There is more awareness that you have to take your fiduciary duty seriously and protect the shareholders."

In fact, Kipnis's own lead attorney has a cautionary lesson from his client's conviction. Problems like the ones that overtook his client "do not come with lights and sirens," says Ronald Safer of Schiff Hardin. They come disguised as ordinary events. And any in-house lawyer, says Safer, after consulting auditors and outside counsel, as Kipnis did, would have felt safe: "And they would have been dead wrong."

Kipnis loved being a lawyer. After earning a law degree at Northwestern University, he joined Holleb, a now defunct Chicago firm. He spent 24 years there, mainly handling real estate closings and corporate transactions, and by the time he left, he was a member of its management committee. "Despite all the lawyer jokes," he said in December at his sentencing hearing, "I view it as the most honourable, collegial profession."

He has been married for nearly 30 years, and one of Kipnis's four grown children spoke eloquently at his sentencing. His son Blair still plans to attend law school, he told the judge. "But if there is one thing I learned from this trial," young Kipnis added, "it is that bad things happen to good people."

After Kipnis was convicted, about 100 friends, neighbours, relatives, and ex-colleagues wrote letters attesting to his character. That in itself was not unusual. But these letters were extraordinary. Many were personal accounts of a man never too busy to help someone in need – whether it was a neighbour with a flooded basement or a secretary at odds with one of Kipnis's law partners.

Other testimonials brought up issues more relevant to the judge. Bruce Clinton wrote about a complex real estate transaction Kipnis handled in 2005, after the lawyer had left Hollinger and started a small real estate practice. "Because it could have been my last major deal," Clinton wrote – he was essentially selling his business – "I wanted to give Mark a bonus for so many years of highly competent representation." He sent him a cheque for $150,000 (£76,000), three times the amount Kipnis had billed. But Kipnis refused the bonus, saying that the amount he had charged was fair.

Former clients praised his ethical standards. Howard Hoffman, a former Holleb partner who once headed the criminal division of the office that prosecuted Kipnis, wrote simply: "I know Kip well enough to know that he is constitutionally incapable of forming mens rea."

So how did this lawyer with a common touch come to work for a company like Hollinger, which (at least in its highest ranks) aspired to royalty? In short, it fell into his lap. His predecessor in the job, Kenneth Serota, had once been a partner at Holleb. When Serota decided to leave in 1997, management asked him to find a successor, and he called Kipnis. Though Kipnis had not been looking for a change, he found the opportunity attractive. The appeal was simple, says defence lawyer Patricia Brown Holmes of Schiff Hardin: "It was something new."

While his base salary matched his draw at Holleb, there was the prospect of more – which doesn't hurt when you have four kids going to college, Holmes points out. And the job was an opportunity to learn a new business and run a law department.

Kipnis apparently didn't take long to decide, but he did have some doubts about the job. Serota spoke of them when he testified at the trial. Kipnis "expressed a concern that he did not have familiarity with the nuances of a public reporting company," Serota noted. "I did not think that that would be a significant issue." Neither Serota nor Kipnis was a securities lawyer, but Serota told his former partner that outside counsel could fill the void.

The passing of the baton from Serota to Kipnis was just one change that affected Hollinger's law department. When Kipnis took over in the beginning of 1998, the company had only been listed in the US for about a year. The acquisition phase had not presented many legal challenges. But the company found itself $2bn (£1.01bn) in debt, and began a massive sell-off to raise cash. Suddenly the company had a flood of revenue with which to pay down debt. The money also brought opportunities for executives who were looking for a cut, and it was the law department's responsibility to make sure that whatever they did was legal.

That was where Kipnis came in. But his task was complicated by an absence of supervision and support. Kipnis may have been hired by Atkinson, but they had little contact after that. Atkinson was based in Toronto and presided over the company's Canadian operations, with his involvement in the US operations unclear even to those in Chicago who theoretically worked under him. But two things are clear: Like Kipnis, Atkinson was not a securities lawyer, and he had no experience working for a company listed in the US.

The man Kipnis reported to was not Atkinson, but Hollinger's president, Radler. And Radler lived in Vancouver, where he spent "at least" half of each month, according to Angela Way, who served as Kipnis's executive assistant. Radler was also a relentless cost-cutter. He was legendary for permanently turning off the escalator in the old Sun-Times building to save money, recalls Ted Rilea, who has been vice president for human resources relations for Hollinger and now its successor company, the much smaller Sun-Times Media Group, since 1992.

If executives offered Kipnis little guidance, neither did they help him assemble a legal team. Rilea remembers that Radler sought to downsize even there. "We have two lawyers," Radler told Serota, thinking of the labour lawyer who handled all the employment work. "We do not need two lawyers." So he fired the other one.

Radler had forgotten Linda Loye, who had been at Hollinger since 1994. According to Way, Loye did the contracts and "sweated the small stuff". Sometimes she seemed more of a paralegal than a lawyer. "Linda's desk was never clear," says Way. There was simply too much to do – even after Radler relented and allowed Kipnis to hire another employment lawyer. Given the complexity of the company, and the volume of work, the size of the department made no sense, says Way: "It was absolutely nuts."

Hollinger's – and Kipnis's – fall came after some things changed. First, the company, which was born in Canada, came under the purview of US regulators in 1996, when it was listed on the New York Stock Exchange. Then came the selling spree, which commenced in 1997 and ran through 2001. As Black and fellow Canadian execs Atkinson, Radler, and CFO John Boultbee unloaded a half-dozen bundled properties, they defrauded the company by paying themselves $60m (£30m) in management and non-competition fees siphoned from payments that rightfully belonged to the shareholders, prosecutors charged. Kipnis was indicted for mail and wire fraud. Days after the indictments were handed up in August 2005, Radler pleaded guilty, and he testified in court against his former colleagues.

The chaotic legal department didn't make wrongdoing inevitable – and did not figure in the trial – but it was part of the environment that apparently permitted fraud to thrive. One more crucial factor contributed – in 1996 a Canadian tax court held that non-competition fees were not subject to tax, and three years later, an appeals court affirmed the decision. Prosecutors charged that Hollinger executives seized on this loophole as a way to pay themselves – Canadian residents – tax-free bonuses.

Non-compete agreements are commonly included in media transactions. Buyers seek protection because they usually purchase not just publications but subscriber lists and advertiser rosters. There is nothing wrong with the agreements per se, but the way Hollinger used them, prosecutors argued, crossed several lines.

The details varied from transaction to transaction, but the government charged that the basic scheme was the same. The requests for non-competition payments came not from the buyers but from Hollinger executives, who falsely claimed that these were insisted upon by the new owners. Also unusual was that the Hollinger execs sometimes requested that the buyers send money directly to them rather than to the company. To be above-board, related-party transactions like these should have been cleared with Hollinger's audit committee and then accurately disclosed in the company's public filings. Not all of them were, prosecutors charged.

The payment on which Kipnis was nailed was probably the most egregious. It occurred in February 2001 and unlike all the other non-competition agreements, this one did not even involve a sale. It was an agreement between Hollinger International and its own subsidiary, American Publishing Company. As federal district court judge Amy St Eve described it in a post-trial ruling, the executives "labelled these payments as non-competition payments – instead of bonuses – in order to take advantage of potential tax benefits." They were never disclosed to the board, and checks that totalled $5.5m (£2.7m) were backdated to 31 December, 2000. "In essence," she wrote, "defendants paid themselves not to compete with themselves."

St Eve went on at the sentencing to cite an admission that Kipnis made during the company's internal investigation. Jonathan Rosenberg, an O'Melveny & Myers lawyer who was investigating under the direction of a special committee of Hollinger's board, testified during the trial about a conversation he had with Kipnis in 2003. The payments were unnecessary, Kipnis had acknowledged to the lawyer, because "there would be no reason for any of the individuals to compete with American Publishing Company," said Rosenberg.

In court last year, Kipnis and Black made an odd couple. Kipnis, the son of a truck driver who died when Kipnis was still in his teens, looked slightly rumpled throughout the trial. By contrast, Conrad Black's father was the president of Canadian Breweries, and Black dressed and acted every inch the aristocrat. He was smooth and imperious, and his prodigious talent (while building his media empire, he wrote books in his spare time) was nearly matched by his grand appetites. And he expected the company to help pay for them. During the trial, the government introduced evidence of the many expenses Black passed along to 'his' company: from vacation jaunts on company planes to the sixtieth birthday party he threw for his wife and 80 of their friends at New York's La Grenouille, charging two-thirds of the $63,000 (£32,000) tab to Hollinger.

Kipnis's defence was disarmingly candid. From their opening statement, his lawyers, Safer and Holmes of Schiff Hardin and Michael Swartz of Schulte Roth & Zabel, admitted that their client had made mistakes. He was not a securities lawyer, he had never worked for a public company – in short, he was in over his head. Some of his errors might have been negligent, his lawyers conceded. But they were not fraudulent. They were the same mistakes made by the company's outside lawyers and auditors – which may appear easy to spot under the microscope of a courtroom, but were not in the bustle of a real-time job.

All of this was to no avail. Did the simple fact that Kipnis was the company's lawyer influence the jury in convicting him? "It was huge," says juror Tina Kadisak, a 34-year-old hairdresser. "He is an attorney. His job is to make sure things are done properly and legally." Moreover, she says, "he did sign those documents. His name was right there in the middle of everything." And, as the corporate secretary, he was management's liaison to the audit committee, she adds.

The defence had the additional challenge of trying to convince the jury that their client was skilled in some areas of the law but ignorant of others. It didn't work, recalls James Kirby, a 48-year-old technical editor at an engineering company. Sometimes his lawyers tried to portray him as "poor old inexperienced Mark," Kirby says. But at other times he was "sharp-as-a-tack Mark".

Whatever their feelings about a lawyer's duty, jurors did not exactly throw the book at Kipnis. In fact, they cut all the defendants lots of slack. They convicted Black of four out of 13 counts he faced; Atkinson, three of seven counts; and Boultbee and Kipnis three of 11 counts each (the judge acquitted Kipnis of one count herself, in response to his post-trial motion). Of the $60m (£30m) in management fees they were charged with stealing, the jury convicted them of defrauding the company out of little more than $6m (£3m). Jean Kelly, a 52-year-old letter-carrier, says she was one of two jurors who were sometimes the last to agree on verdicts. "[Those] of us who had doubt had a hard time thinking there was criminal intent," she says.

The big issue for the jury was whether the non-compete payments were disclosed in some manner – or any manner, even if the board's audit committee was not informed directly, says Kelly. As long as there was disclosure in a financial filing, the jury gave the defendants a pass.

The defendants' sentences diverged sharply. On 10 December Black was sentenced to six-and-a-half years in prison; Boultbee to 27 months; Atkinson to 24. Radler's plea landed him 29 months. Only Kipnis was spared prison. Calling him "clearly the least culpable person in this scheme," St Eve gave him five years' probation, six months' home detention, and 275 hours of community service. Some observers suggested that the challenges Kipnis faced may have resonated with St Eve, who early in her career had been an in-house lawyer herself at Abbott Laboratories.

Whatever the impetus, there was elation in the courtroom from Kipnis's supporters when St Eve announced her decision. But Kipnis's relief did not cancel his dismay at the verdict – he joined the other defendants in appealing their convictions.

For a time after he resigned from Hollinger and was indicted, Kipnis practised real estate law. As his trial approached, he stopped practising altogether. In January 2006 he, his wife, and son Blair bought a struggling sign shop in suburban Chicago called Sign-a-Rama. At his sentencing hearing, he told the judge that the sign business, like the law, was "an honourable, hardworking service business". But it was also physically demanding – at the age of 60, he said, he was not sure it was something he could sustain.

The sentencing hearing was the first and only time Kipnis publicly addressed the charges. Speaking to a packed courthouse after a full day of hearings that ended with his own, he rejected the way he was portrayed by prosecutors during the trial. Nor would he accept the 'St Mark' tag jurors had hung on him. "That's not me either," he said. "I'm just Mark Kipnis." He continued: "99% of my time, Judge, I believe I was competent. I believe I did do a good job. It was that 1%, the compliance aspect, that should have taken much more of my time. I admit," he added, "I did not fully understand the magnitude of those responsibilities."

A few weeks later, his lawyers drew their own lessons from the trial. "As fine a lawyer as Mark was in real estate and private company transactions," says Michael Swartz, "he did not have the appropriate background and experience to fully appreciate what was expected of him." Nor was he completely familiar with all the documents he signed, some of which were mostly drafted by outside lawyers. "You don't get a pass," Swartz observes, "just because you're not intimately familiar with the document that your name is on."

The most poignant lesson might have been the loss of a beloved career. "I love being a lawyer," Kipnis told the judge, knowing that, no matter how favourable her sentence, he would soon be surrendering his law licence. "I miss it terribly."

A version of this article also appears in Corporate Counsel, a US sister title of Legal Week.