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Lawyer Eddie Greenspan at his office on King St., Toronto, September 22, 2011. Photo by:

Edward Greenspan had never seen a cross-examination in the United States. And then, after nearly 40 years in criminal law, almost all of them as Canada's best-known lawyer, he went to Chicago to defend media baron Conrad Black on fraud and other charges.

It didn't start so well. "When I got up and asked a question, the prosecutor – who was behind me, I couldn't even see the prosecutor – said: 'Objection!'" Mr. Greenspan said in a frank interview published five years ago in the Advocates' Journal. "And I'm waiting to find out the objection, and the judge said: 'Sustained.'"

The experience showed that Mr. Greenspan, who died of heart failure Wednesday morning in his sleep at age 70, was not content to rest on his laurels. He continued to take risks, to find new challenges, to throw himself into learning new things. He was a force of nature and a lawyer to his core, as exemplified by the reading material he took on his honeymoon – the Criminal Code.

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"The law was not just a business to Eddie," Supreme Court Justice Michael Moldaver, a friend and former colleague, said in an interview. "It was a part of his being, and that really set him apart from many others."

Or, as Mr. Greenspan put it: "Advocacy is in my blood. It's the air I breathe."

Whether he lost or won the Conrad Black case – Mr. Black went to jail for three years, but it could have been a lot more – the result seems not to have harmed Mr. Greenspan's reputation.

Anthony Moustacalis, president of the Criminal Lawyers' Association, said Mr. Greenspan ranks with the great advocates of the past several decades in Canada, such as David Humphrey Sr., G. Arthur Martin and Austin Cooper.

Steven Sturka, a Toronto lawyer who attended the 2007 Black trial and wrote a book about it, said Mr. Greenspan accomplished something exceptional for Mr. Black. "It certainly was a bumpy ride and it wasn't perfect, but at the end of the day it can be looked at as a grand achievement." He added that, from his interviews with Mr. Greenspan, "I believe he was motivated by a sense of justice. He strongly believed Conrad Black was an innocent man."

Justice Minister Peter Mackay reacted to the famed lawyer's death. "Mr. Greenspan was a brilliant lawyer, a man of great intellect and principled action," he said on Twitter.

Mr. Greenspan had a trademark style, observed veteran civil lawyer Alan Lenczner, who went up against him in a number of debates over the years. "He had an unerring focus on the heart of the matter. He'd exploit the weaknesses right away. He didn't bother with niceties. It was like an arrow coming off a bow and straight to the bull's-eye."

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Mr. Moustacalis, who last saw Mr. Greenspan at an event just a few weeks ago, called the gregarious lawyer "a lion at the bar" who worked tirelessly on all his cases.

"Even though he got a lot of publicity, there was a lot more good that he did that went unknown," Mr. Moustacalis said. "He helped people on a pro bono basis and always had an ear for anyone who needed some help or advice."

Mr. Greenspan had the knack of changing the air in the courtrooms he entered. Stephen Williams, an Ontario author he defended pro bono, describes 200 people trying to jam into a Toronto courtroom made for 60 to see Mr. Greenspan in action. Although his friends say he was shy, he was also a born performer. "He had a bit of a Jackie Gleason quality," said writer George Jonas, his close friend.

That quality was on display less than a month ago when he introduced Vancouver lawyer Richard Peck as the winner of the 2014 G. Arthur Martin Award for contribution to criminal justice. For 10 minutes, with a straight face, he uttered not a word of praise, only criticism.

On a separate occasion, also in front of an audience of lawyers, he spoke humorously about the result in the Garth Drabinsky white-collar crime case. Referring to Superior Court Justice Mary Lou Benotto, he said: "I saw 150 years written on her face, and I talked her down to seven. I've still got it."

He and Conrad Black did not see eye to eye after the Chicago trial. Mr. Black published a book in which he praised and criticized Mr. Greenspan. Mr. Greenspan published a 2,100-word response in The Globe and Mail. But on one issue they agreed: The U.S. justice system was deeply unfair.

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"They're nuts down there," Mr. Greenspan said in the interview in the Advocates' Journal. "The system has gone amok."

He expressed his pride in the Canadian justice system, saying that prosecutors here are obliged to disclose witness statements promptly to defence lawyers, and that in the U.S. such disclosure tends not to happen until partway through the trial. He also said that fair-minded prosecutors, such as Patrick LeSage of Ontario, later a chief justice, can't be found in the U.S.

"He was the fairest of them all. I couldn't beat him. And in four jury trials that I had with him, I didn't. He was fantastic. Those people don't exist in the United States. They're doing it to get employed. They're known for 'I convicted Conrad Black' or 'I convicted Tyco or Enron or WorldCom,' and they end up making fortunes. But they cheat, they lie, they're untrustworthy and, for them, it's all about getting an accused at whatever cost."

Mr. Greenspan, who taught at two Toronto law schools, co-edited an annotated Criminal Code, hosted a radio and television show for 17 years and had an enormous caseload, much of it far from the limelight, told his friends that he didn't expect to outlive his father, who died at 42 of a heart attack, and that that was why he worked so hard.

"What made him tick, was, in my estimate, a sense early on that he had things to do, miles to travel, no time to lose and it would probably always be that way," Bill Wilkerson, a mental-health advocate and a lifelong friend of Eddie and his brother Brian, said.

With a report from The Canadian Press

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