PORTLAND — Twenty-five years ago this Friday, Maine’s most infamous drug smuggler received a headline-making criminal sentence that many considered a slap on the wrist.

While several members of his marijuana-importing business were sentenced to years in prison, Harvey Prager lived in his Portland home with his wife and children and took care of dying AIDS patients. As he served his sentence, he attended the University of Maine School of Law.

He could have received 15 years in prison and a $125,000 fine after pleading guilty in federal court to conspiracy, possession and importation of marijuana.

Now the former pot pirate is in courtrooms for a different reason. Prager operates a successful Boston law practice, helping other lawyers who may have legal problems of their own.

“I wake up every day grateful for the second chance I received,” Prager said in a telephone interview last Sunday. “My way of paying back is working as hard as I can for deserving people.”

‘Pursuing a lifestyle’

Prager, a New York City native, graduated with honors from Bowdoin College in Brunswick in 1969, then taught American literature for a year in Argentina, where he had relatives. In 1971, he started graduate school at Harvard University.


He intended to be a historian, but at Harvard he started smoking marijuana, a practice he said led him to drop out of school. Instead, he worked as a sailboat crew hand, delivering yachts up and down the East Coast.

He and two friends bought “an old wreck of a schooner” and spent a year in Key West, Fla., renovating the vessel by day and sleeping beneath it at night. Once fitted out, they chartered the boat, sailing it for hire throughout the Caribbean.

In 1975, Prager and his friends received an unusual business proposal from an acquaintance in Boston: Sail to Colombia to pick up and deliver two tons of marijuana to Maine, for a fee of $25,000 each. The crew accepted the assignment.

“We then felt obligated to make the trip again. We did all this without much reflection,” he said. “We didn’t think of ourselves as criminals. We saw marijuana as something that had to do with raising social consciousness, with peace. It was about pursuing a lifestyle.”

Prager and his friends went on to make annual 3,000-mile voyages from Colombia to Maine, arranging nocturnal drug drop-offs in local waters that sometimes involved several other boats. Considered the leader of the crew, Prager even visited Colombia to arrange some purchases and shipments personally. In six years, the smuggling ring landed a total of 20 tons of pot in Maine, worth an estimated $83 million.

“It was wrong, but it obviously grew from very humble beginnings into something that was much bigger,” he said.


The boom is lowered

Eventually, though, Prager’s luck ran out.

In 1981, a U.S. Coast Guard patrol in Penobscot Bay noticed that one of Prager’s boats was riding low in the water. The craft was searched, and seized when it was discovered to be carrying five tons of marijuana.

The seizure, and increasing pressure from his Colombian contacts to transport cocaine, convinced Prager to retire from the business. So he stopped shipping pot, moved to the French West Indies with his girlfriend, and built a house.

But the law was on his trail. A crew member of the seized vessel implicated Prager and, in 1984, he was indicted.

Although Prager had frequently traveled under his own name from his new home to the United States, he decided not to come back again.

“I didn’t have the courage (to go back to the United States),” he said. “As a lawyer today, it would be a no-brainer: I’d say, ‘You have to go back.’ But it was tough decision for me, and I made the wrong choice.”


With more than $1 million in assets around the world, Prager became an international fugitive from justice. He traveled throughout Europe, married his wife, Sandrine, and worked as an art dealer under the alias of Harvey Israel. In 1987, however, a Scotland Yard investigation of a London bank heist opened a safe-deposit box with Prager’s passport, revealing his true identity.

He was jailed in the United Kingdom, pleaded guilty, and was extradited. He soon found himself in a Portland courtroom, facing U.S. District Judge Gene Carter.

Controversial sentence

Carter was known for handing down tough sentences in drug cases, and had already put Prager’s conspirators behind bars for a total of more than 50 years. Nevertheless, Carter agreed to listen when Prager proposed an unusual penalty.

Prager would turn over most of his assets, including Swiss bank accounts and real estate in London, Paris and the Caribbean. And he would open an AIDS hospice in Portland.

The proposal was the result of months of planning, and had the support of Portland doctors and state agencies.

But Carter was skeptical.


“On the morning of the sentencing hearing (Carter) intended to send me to prison,” Prager said.

Prager made his case, and Carter relented, allowing Prager to provide hospice care for terminal-stage AIDS patients as a condition of a five-year probation. Before a hospice could be built, the sentence was modified to reflect that Prager had already started caring for patients in his Danforth Street townhouse.

The sentence generated scorn from critics who felt Prager got off too easily. But in the late 1980s, Portland was experiencing the first terrifying wave of AIDS deaths — and Prager had recently spent some time helping a cousin start an AIDS hospice in Argentina, the first in South America.

“Once I started meeting people dying of AIDS, it was impossible not to want to do something,” he said.

Prager cared for 15 patients over the five years of his probation. Some people publicly claimed that he neglected his wards. Others, such as Dr. Michael Bach, then a Portland AIDS specialist who oversaw Prager’s care-giving, praised him. Prager defended his work.

“Patients died with me holding their hands,” he said. “You can’t overestimate how difficult that job was. And for me, it was transformative. … I haven’t been the same person since.


“As (patients) died, they would help me understand what we’re supposed to be doing here, and the importance of making amends and coming to grips with what you’ve done.”

A different brush with the law

Besides coming to grips with his past deeds, Prager started thinking about what he would do next.

“Law was something I knew I’d be good at. As early as high school, I felt it was something I could do well,” he said. He had first-hand experience with the legal system. Plus, he noted, the law school was just a few minutes away.

Prager graduated in 1994 near the top of his class, and earned a prestigious clerkship with the Maine Supreme Judicial Court. He then applied to practice law in Massachusetts. The decision to admit him to the bar reignited controversy.

“The flak started again, understandably,” he said. “People certainly had a right to debate.”

In Maine and nationwide, the public wrote newspaper letters calling the decision ”outrageous” and an ”insult to all law-abiding citizens.”


“It’s ridiculous. He couldn’t be a security guard, but he can be a lawyer,” Michael Chitwood, then Portland police chief, said to the Associated Press. “It’s a sad state of affairs.”

But Prager’s admission to the bar was also endorsed by such figures as the federal prosecutor in his case and Justice Howard Dana of the Supreme Judicial Court. After a hearing in December 1994, the Massachusetts Board of Bar Examiners found that he had rehabilitated himself enough to pass its admission requirement of “present good moral character.”

Today, from his eighth-floor office in downtown Boston, Prager represents other bar candidates and fellow lawyers as they deal with “character” issues of their own, involving bar admission, disciplinary defense and reinstatement. And he’s just finished co-authoring a book on attorney regulation and discipline.

“My experience has translated itself into something I take very seriously,” he said. “I do what I do with a great deal of passion. … Nobody can care about this more than I do.”

Prager, now 66, wouldn’t comment when asked for his views about Portland’s Nov. 5 referendum on legalizing recreational marijuana use. He said he smoked his last joint in 1981, and he acknowledges his guilt.

“Smuggling was absolutely wrong, and one of the reasons was that it was against the law,” he said. “The law is paramount.

“But under the law, rehabilitation is an important concept. … and I’m proud to be a lawyer in the best sense, helping other lawyers who deserve a second chance.”

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