John Pappalardo was born to be a leader. Just ask his childhood friend Kimball Hobbs.

“In the Boy Scouts, John was taking a canoe test for his merit badge,” remembers Hobbs, a former banker who is now a student at the University of Maine Law School. “He had to canoe against a crosswind and failed the test. He was truly embarrassed, but he took it as an incentive, not just to redeem himself and pass the merit badge, but to become an expert. And he did just that.

“Later, between our freshman and sophomore years in high school, we went on a Boy Scout canoe trip in Canada. There were 15 of us, three each in five canoes. The idea was that two would paddle, while one would rest. Nearly all of us saw this as a chance for some leisurely sightseeing and fishing. John saw it as a chance to set a 10-day distance record. Somehow — by force of personality — he got all 15 of us to paddle for 10 days straight. No one got much fishing in on that trip, but we did bring home a distance record.”

That is pure Pappalardo. Driven, competitive and masterful in getting people to paddle in the same direction. As co-chair for the white-collar crime section for Greenberg Traurig (GT) and comanaging shareholder for its Boston office, Pappalardo, 56, has used his innate leadership skills to become an internationally celebrated lawyer for his clients — one of whom happens to be Russian billionaire Mikhail B. Khodorkovsky.

Pappalardo was chosen to help defend Khodorkovsky — Russia’s then-richest man and its major funder of opposition political parties — after an exhaustive process that resulted in an interview in August 2003 with one of the mogul’s representatives in Washington, D.C. The former majority co-owner of Yukos Oil had been arrested on charges of fraud and tax evasion and had drawn the wrath of Russian president Vladimir Putin.

After being hired, Pappalardo traveled to Russia to gather information. But because U.S. lawyers have no standing in Russian courts, all he and his colleagues could do was advise their Russian associates. On May 17 of this year Khodorkovsky, 42, was convicted on six of seven charges, and was later sentenced to a nine-year prison term. By most credible accounts, Khodorkovsky never had a chance against the government.

“Khodorkovsky is a highly intelligent, extremely principled man who knew in advance that this fate would befall him,” Pappalardo says. “As a lawyer I can tell you the charges were internally inconsistent on their face and evidence at the trial was in many cases nonexistent. I believe [Khodorkovsky] didn’t commit the acts that were charged, many of which weren’t crimes in the first place. Clearly, the Russian system did not work in this case.”

Pappalardo is powerfully built, if a bit softer than in his days as a 240-pound football lineman at Maine’s Bowdoin College. Dressed in gray suit pants, white shirt and brown-print tie, with closely cropped hair and rimless glasses, he looks like your local CPA. But how would your local CPA have reacted to the words Pappalardo heard on his voice mail en route from London to Moscow, warning him of “a serious problem” if he entered Russia. Pappalardo never contemplated turning around. “When you prosecute a case, you don’t consider what a defendant could do [to you],” the former prosecutor says. “If you did, it would impact the case.” The implication: A defendant’s attorney should do no less.

Although his client is currently behind bars, Pappalardo and the defense team can claim some significant victories in the case. He points out that requests by the Russian government to freeze Khodorkovsky’s sizeable assets and seize his documents have been successfully defended in courts in Lichtenstein, Switzerland and the United Kingdom.

“John is not necessarily the most glib or fastest thinker, but an extraordinarily deep one,” says Evan Georgopoulos, 38, a Greenberg colleague who assisted in the defense. “He has the ability to slow things down and think through problems. He and others have conveyed to the international community the failure of the Russian courts to uphold the rule of law and helped prevent foreign courts from being complicit in that lawlessness.”

A Buck for All A’s

Pappalardo gets his drive from his parents, who challenged him at a young age to achieve at a high level. “When he was in the second grade, his mother put down a challenge: ‘Get all A’s and I’ll give you a dollar,’” remembers Hobbs. “For years after, she loved to tell how on report card day he would throw open the door and announce, ‘Ma, you owe me a buck.’”

At Hingham High School, Pappalardo was a star athlete and the kind of leader who didn’t run for office but gave people nicknames and made everyone feel comfortable. His people skills came to light almost the moment he arrived at Bowdoin in 1967.

“There was a meeting over the state of the football program,” recalls his college roommate, Tom Carey, now a lawyer in Rumford, Maine, “and John stood up and said how important football was to him, how it was a big reason he’d come to Bowdoin. He hadn’t prepared anything; he just spoke his mind. The upperclassmen were impressed and the coaches were looking at each other in amazement.” Pappalardo started all four years.

After Bowdoin, Pappalardo attended Boston’s Suffolk Law School, earning his degree in 1974. After graduation, he spent four months working at a Goodyear Tire warehouse while waiting for his bar exam results. Then, while his wife, Karen, supported them by teaching elementary school and figure skating, Pappalardo spent about six months volunteering at the office of Norfolk County D.A. (now congressman) William Delahunt. When a lawyer there took ill, he was thrown into a court case. “It was as if a light was switched on for him,” Hobbs says.

Hired by Delahunt in November 1975, Pappalardo prosecuted about 250 cases in the Norfolk office. In 1978 he was selected as a counsel on the state’s Ward Commission, which was investigating payoffs to politicians from the McKee-Berger-Mansueto consulting firm. There were televised hearings and interviews with 140 witnesses. The commission’s 12-volume report, issued in 1980, cited a culture of corruption as a way of life in Massachusetts. As a result of the report, legislation was passed creating a state inspector general.

In 1981, Pappalardo made the natural segue into prosecuting for the state attorney general’s office under Frank Bellotti. As chief of the public integrity unit, Pappalardo investigated illegal activities by the Massachusetts Bay Transit Authority and got 64 indictments from a Suffolk County Grand Jury.

Pappalardo joined Bill Weld’s U.S. Attorney’s office later that year. “The conventional wisdom is that Weld is smart and lazy,” Pappalardo says. “He’d be in the office at 7 a.m. He loses interest and moves on, but he’s not lazy.”

He spent the next 13 years racking up prosecutions at both the state attorney general’s office, where he returned for a couple years in 1987, and later as the head of the U.S. Attorney’s Office, from 1992 to 1993. He jumped to the private sector in 1994 and landed at Greenberg Traurig in 2001.

The transition from prosecuting to defending may seem odd to some, but not to Pappalardo. “The camaraderie in the U.S. Attorney’s office is duplicated here,” he says. “That’s why it’s not hard to make the transition.”

Pappalardo keeps a punishing work schedule, spending half his time meeting client needs abroad. He rarely has time to sightsee, but he relishes the places he’s visited — especially Russia. “If you like museums and historical culture, it’s a place not to be missed. The time to go is during the summer, the time of the white nights.”

In what little free time he does have, Pappalardo enjoys collecting wine (“I’d be a better wine collector if I weren’t such a great wine drinker”) and spending time in his Bretton Woods, N.H., ski house with Karen and their 17-year-old son, Jonathan, a high school senior.

For a guy who so thoroughly enjoys new challenges, can his next career move be far away? Pappalardo insists it is. He’s content at GR and not planning to go anywhere. “We’ve never had a merger, so you preserve the culture — the people who come here from other firms excel in this environment. I can’t be a bigger cheerleader for this firm,” he says.

But if he could, he’d no doubt have everyone in tight formation, performing perfectly under his direction.