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Indeed, much of Nantucket has to trust Lepore at one time or another. “When you’re up to your ass in alligators, Tim Lepore is one of the people you want to have with you,” says Margot Hartmann, the chief executive officer of Nantucket Cottage Hospital. “He is gutsy. He does not run. That’s why he’s become the backbone of the island.”
And why he can end up stepping into almost any delicate situation, strictly medical or not.
Billy Dexter got to know Lepore in the late 1980s. He began visiting the doctor’s office for routine things, but found Lepore good to chat with. And they shared an interest in hunting; Dexter liked black-powder rifles, and he once carved Lepore a squawking duck call. He would drop by Lepore’s house with a black Labrador retriever three times the normal size, and when Lepore’s children saw him approaching, they would hide in the bushes and yell: “Billy Dexter’s here, and he’s got a warthog with him.”
“Tim was the only person who was kind to him,” recalls Michelsen. “Tim thought he was interesting.”
But Billy Dexter had a problem—and a predilection. As Lepore described it, Dexter was “a nice guy, but when he drank, he went off the radar.”
And, apparently, into someone else’s barn. On October 7, 1988, the owner of a Madaket Road stable called the police to say that she had noticed a water pail had been removed from one of her horse stalls and that the horse kept rubbing its hind quarters against the stall, according to a Nantucket police report. The woman believed “that the horse had been sexually assaulted” and “also observed a pair of black Farah pants at the back of the stall. The pants were placed into evidence.”
The following day, a second police report was filed: “William Dexter called the station to inquire about some pants that he was missing.”
Officers put two legs and four legs together, went to Dexter’s Cliff Road house, and arrested him on two counts of sodomy. “Suspect has a history of similar crimes,” police records stated, “and is familiar” with the barn owner “and her stables.”
The court case caused a stir. Lepore’s neighbor Chris Fraker expressed the island’s and Lepore’s dilemma succinctly: “What do you do with the town weirdo that’s doing horses and sheep? Tim’s view was ‘I don’t give a flying Friday what you do; just don’t get caught.’” But “people didn’t like it anymore, so it went to court.”
The assistant district attorney asked Lepore to recommend whether Dexter was criminally liable. Lepore could have taken a hard line. After all, he didn’t know the forty-four-year-old Dexter especially well, and no one would say there was an advantage in defending a guy who was into bestiality. But Lepore’s judgment was that Dexter did not deserve to be vilified. “At heart he was a very sad, depressed guy. He would drink and have a dalliance with a horse. I knew Billy Dexter, and he was no stallion.”
So Lepore wrote a letter to the district attorney and scheduled an appointment for Dexter with a therapist at Nantucket Counseling Services. According to the Nantucket Inquirer and Mirror, the therapist, Truman Esau, testified that Dexter should be hospitalized, not jailed, because he suffered from chronic alcohol dependence and zoophilia, having “admitted that having sex with animals is his personal preference.”
Lepore acknowledges that Dexter’s behavior was “a distasteful thing. This wasn’t a guy who was going around knocking over mailboxes.” But “I didn’t think he represented a clear and present danger to the island.” Dexter was eventually sentenced to a hospital instead of jail. A year later, though, he was arrested on federal firearms charges for having a sawed-off shotgun. It was a weapon that Lepore believed Dexter used for shark fishing, but this time Lepore didn’t get involved. “I don’t write many letters for felons,” he said. But he doesn’t throw patients overboard either. When, a few years later, Dexter suffered fatal heart failure, “I took care of him.”
Dexter’s brand of deviance may have been unusual, but Lepore has treated any number of Nantucket’s odder ducks. “Not every miscreant is mine,” he insists. “Just most.”
Lepore has been pulled into some of the island’s most notorious criminal cases. He’s the person who pronounces murder victims dead, fixes people who are stabbed or shot, analyzes alcohol and drug levels in passed-out substance abusers, and helps evaluate whether crime suspects are mentally sound enough to go to jail.
Thomas Shack, chief of operations for the Cape and Islands District Attorney’s office, remembers a recent high-profile case in which a woman seriously injured another woman in a bar fight. Shack’s job was to undercut Lepore’s testimony about the victim’s intoxicated state.
“He has this sort of ‘aw shucks’ manner—you come in contact with that pretty quickly when he’s on the witness stand,” Shack observed. “Here I am, having to cross-examine him and kind of be tough on him, keeping in mind that this person might end up saving my life one day.”
To do the work that Lepore does, for as long as he has done it, an understanding of the island is imperative. While Nantucket nurtures an affable feeling of community, it can also be a place of individual isolation. The transparency of a small town coexists with a pointed respect for privacy. And an attitude of irreverence vies with a realization that islands can, in a quicksilver second, leave people uniquely vulnerable or make their lives utterly unpredictable.
“People don’t realize things happen on Nantucket,” says Janine Mauldin, an island police officer. “They think it’s a nice quiet island.”
For one thing, there is the influence of the sea, the surf, and the sand. Collapsed sandbars can alter the channels that sea water moves through, creating sudden strong currents in unanticipated places. That can endanger swimmers and boaters, causing accidents or drownings.
Jet Ski collisions, man-overboards, and other watery mishaps land in Lepore’s lap, like the time the singer Jimmy Buffett’s seaplane flipped over as Buffett, an experienced pilot, was trying to take off from Madaket Harbor. The plane was badly damaged, but Buffett managed to swim to shore, where Lepore X-rayed him, identified minor injuries, and released him so he could go on to waste away again in many a Margaritaville.
Natural calamities can instigate human mischief, like the disturbing act of the unknown marauder who committed the federal crime of mutilating the tail of a dead humpback whale that beached in the summer of 2011.
And one fall day in 2010, the bones of a human leg, still in a sock and work boot, surfaced on the sand at Great Point. Police called Lepore. “Tim is the guy that I’m going to bring the bones to,” notes Steve Tornovish, a detective. “He’s the absolute master of the universe down here.”
Lepore immediately sized things up: “A left tibia and fibula. No cut marks or bullet holes. It hadn’t been gnawed on. The boot had barnacles on it. The bones had been cleaned of flesh. It had been in the water awhile.”
More than a year later, verifying suspicions of many Nantucketers, state authorities determined the leg belonged to Jonathan Hemingway, a Nantucket landscaper who had disappeared one night in March 2010, when he was sailing his powerboat from Hyannis to Nantucket with his family and apparently fell overboard while his wife and children slept below.
The severed leg closed the book on one island mystery. But there is always another.
In July 2011, Lepore found a plastic bag on his desk with another human tibia inside. Someone had found it on the beach near Coatue and brought it—where else?—to Lepore. “Semifresh,” he said. “Still smelled.” It came from an adult over thirty, he deduced, noting that the bone’s growth plates had fused, making it too developed to belong to a child. He sent it to Boston. No idea to whom it belonged, but on this island, “there’s always folks missing.”
What’s never missing on the Nantucket that Lepore encounters every day is a spirit of individuality some people take to stubborn extremes. Gene Ratner gained national attention for his drive to save the four-bedroom home he built more than thirty-five years ago perching just above the great sweep of water off Madaket Beach. As wind, water, and
time eroded shards of Nantucket’s fragile coast, Ratner’s house was increasingly in the crosshairs as the steps he took to protect it clashed with island environmental rules. Finally, in September 2010, after a hurricane left the house crumpled but standing, officials condemned it, and Ratner, by then eighty-five, was forced to take it down.
A few months later, in another Nantucket-versus-nature moment, came a showdown with Joe Dooley, a scalloper living with a passel of dogs on a thirty-year-old fishing boat he had bought for $10 and moored in Nantucket harbor in 2007. The boat, the Miss China, had a broken engine and was unable to move under its own power.
Nantucket officials once had to rescue six Dooley dogs that jumped overboard, and the Coast Guard once had to pump thousands of gallons of fuel out of the boat so it wouldn’t sink. Then, in December 2010, a pounding winter storm swept the Miss China off its mooring and beached it in the sand near Nantucket’s Brant Point lighthouse. Officials tried to get Dooley and his dogs off the boat, afraid it would break loose and sink or crack up, creating a navigational disaster for other ships.
Dooley refused. “They want to get me off the boat so they can claim it for salvage,” he told the Inquirer and Mirror. “I’ll freeze to death or starve to death before I give them that satisfaction.” It was nearly a week before he finally gave in.
The miles of ocean between Nantucket and America make some people feel invisible, undetected, and emboldened. Perhaps that’s why, on the Friday of Memorial Day weekend in 2010, Pamela Morgan committed Nantucket’s first bank robbery in more than two hundred years.
There’s a reason why “bank robbery hasn’t caught on,” notes Lepore. “They got no place to go.”
This realization occurred a little too late to Morgan. But then, she had a lot on her plate. She had a ball of tinfoil full of fake identification cards with different aliases. She had a string of larceny convictions in Ohio, Oregon, and California. And in 2009, she had been arrested by the Secret Service after trying to jump the White House fence.
So who knows what she thought would happen when she walked into a Nantucket branch of the Bank of America, began chatting to the teller about letters she had written to Fidel Castro, and presented five crumpled $1 bills that were so obviously counterfeit some had George Washington on both sides. “She was telling me there were people after her, that her life was in danger, and if I knew her situation, I would know why she was doing this,” the teller testified. Told her money was no good, Morgan pulled a note from her backpack that read: “I don’t want to hurt anyone. Give me the money.”
Morgan walked out with $3,000 but didn’t get far. She crossed the street to Sheep to Shore, a knitting shop, then slipped into a post office, where a police officer confronted her. She explained, the officer recounted later, that she’d tried unsuccessfully to use the counterfeit bills at several stores, and that she’d foil-wrapped her ID cards because “the government was tracking her through microchips in her identification” and “the tinfoil didn’t allow them to track her like that.” Later in jail, she accused the Nantucket police and the FBI of tampering with her milk and bed sheets. Her case is pending, and she is being held in a psychiatric facility.
As an out-of-stater who’d been on the island less than twenty-four hours, Morgan was a washashore of the briefest variety. But people with deeper island roots have tried to get away with things too, often right under their neighbors’ noses.
Not long after the Great Nantucket Bank Heist, one of Lepore’s nurses was enjoying the evening air when a posse of local cops, state police, and federal agents tromped across her porch, barreling toward the house of her Belarusian next-door neighbor, Mikalai Mardakhayeu. Turns out he was running an international fraud conspiracy, a phishing scheme in which he and his cohorts pretended to prepare tax returns for people across the country while actually using their personal information to siphon off $200,000 in federal and state tax refunds.
That was nothing, though, compared to the scrimshaw-smuggling conspiracies. Two old-timers in two separate cases went too far in the name of art, specifically the practice, begun in the nineteenth century, of carving bones and teeth of whales, walruses, and other sea mammals. One, Charles Manghis, long a bearded and bespectacled presence at his shop on the Old South Wharf, was a scrimshander, an artisan who etched lighthouses and ships into ivory and whale teeth and had even carved presidential seals for both presidents Bush. The other, David Place, owned Manor House Antique Cooperative.
Both men were convicted of conspiring with a Ukrainian smuggler and a middleman in California to illegally import the teeth of endangered sperm whales. Manghis, who was tied to some 375 whale teeth, admitted his nautical transgression. Place, accused of smuggling $400,000 in teeth and tusks, did not, saying the Ukrainian hornswoggled him. And a handful of independence-conscious Nantucketers rose to his defense, signing a petition arguing for his sentence to be reduced.
“We have a proud history,” wrote the organizer of the as yet unsuccessful effort, “of taking care of our own.”
But as Lepore has learned from experience, sometimes Nantucket is unable to take care of its own. Trudie Hall was twenty-three and pregnant when she disappeared in July 2010, last seen when she left the island for what was believed to be a short trip to Cape Cod. Hall, a Jamaican immigrant, American citizen, and Nantucketer for ten years, turned out to have a secret even her mother claimed not to know. She had married two different men within six months of each other and not divorced either, possibly in an immigration scheme in which she reportedly received money to help the men get legal status.
To thicken the plot further, the father of Hall’s unborn child was a third man, a former Nantucketer, now on Cape Cod, who was married and had previously been convicted of stealing $8,000 from Nantucket bus fare boxes.
After Hall disappeared, her rental car was found in a commuter parking lot, with blood and bullet casings inside. The investigation continues, although police and her mother assume she’s dead.
Lepore was as fascinated as the rest of the island by Hall’s uncertain fate. But he was not surprised that Nantucket formed the nexus of Hall’s hidden world. He knows the island too well.
As far as most Nantucketers were concerned, Thomas Johnson, aka Underground Tom, was another mysterious disappearance, someone who fled the island more than a decade ago. Lepore, however, knew better.
Johnson grew up in Binghamton, New York, one of seven children of a city judge. As a teenager, he built his first log cabin in the Pennsylvania woods, where he often retreated. He briefly attended community college, reportedly writing on every test and assignment, “When Johnny comes marching home again, hurrah, hurrah.”
When he was twenty, his father died in his arms of colon and liver cancer. Soon Johnson, who stayed home to care for his mother, developed a drug habit and hired himself out as an international drug courier. In 1983, he was arrested in Italy for trying to smuggle in more than $2 million of Thai heroin, stitched into the lining of a suitcase he was supposed to deposit in a train station locker in Rome.
After two and a half years in an Italian prison, he was released on house arrest, but escaped, began kiting checks, and eventually came to Nantucket, where he said he scoped out the site for his underground home by spending “a month of Sundays” sitting in a nearby tree on Boy Scouts land near Lovers Lane. In just five weeks, he dug a hole with a shovel, paid less than $150 for materials, stole or “liberated” other supplies, and built what he described as his “self-help tank,” saying, “I’ve gone into the earth, almost like a seed, to germinate.”
Johnson germinated largely in solitude, weathering hurricanes and snowstorms underground, his house insulated with rubber and covered with topsoil and sand. Its portal, camouflaged by limbs and dead leaves, was a hatch inlaid with a small glass window.
Inside, a ladder descended eight feet into the earth, which opened into a three-room chamber outfitted with a striking array of comforts: cedar paneling, a Belgian stone floor, a stained
glass skylight obscured by a patch of blueberry bushes, a homemade chemical toilet, a battery-powered television, and a shower made from a plastic tube hooked to a water jug. A cubby cut into one wall served as a pantry, keeping bottles of milk and cups of Jell-O pudding cool even in summer.
At first Lepore didn’t know where Johnson lived. He’d see him riding around on his bike or picking up scrap wood. Johnson supported himself as one of Nantucket’s legion of part-time carpenters and painters who build and maintain summer people’s homes. He drank at bars in town and occasionally got in fights.
Johnson went to tremendous lengths to conceal his house, using what might be called sleight of foot. He created shoes that made impressions that looked like deer hooves, placed his feet down as he walked in the linear pattern that resembles deer tracks, and varied the path he took to his door by taking one of fifteen different trails. He dismantled deer stands that hunters erected in the scrub pine forest to discourage them from hanging around, lest they spy his six-foot-four-inch frame lumbering toward his lair.
But Underground Tom had medical issues, including joint and back pain, and he sought out Lepore. No doubt he considered the doctor something of a kindred spirit. Lepore’s office is as intricately decorated and anti-establishment as Johnson’s belowground bunker.
There are skulls, arrowheads, snake skin, turtle shells, fish jaws, and antlers. Books include Latrinae et Foricae: Toilets in the Roman World and Philip Roth’s The Plot Against America. And some of Lepore’s many signs would appeal to his iconoclastic patient: “It could be that the purpose of your life is only to serve as a warning to others” and “Carthago delenda est” (Carthage must be destroyed), the famous phrase by the Roman leader Cato, which often signifies a single-minded intensity for total victory against one’s enemies. In his waiting room, Lepore has posted a reference to America’s favorite fantasy tale: “Nobody gets to see the wizard. Not nobody. Not no how.”