Pirates in the Caribbean

“The law of the jungle and the sea are your only teachers.”

-Bob Dylan, Jokerman

Who was I?

I was raised to survive chaotic situations. My parents, capitalist hippies, were like Travis McGee in the John D. MacDonald novels my brother and I read when we could get our hands on them. The fictional McGee lived on a 52-foot houseboat he won in a poker game called the Busted Flush, operating out of a slip at Bahia Mar Marina in Fort Lauderdale, Florida.

We also episodically lived on a sailboat out of a slip at Bahia Mar Marina. And like McGee, my parents had a philosophy of “checking out” from society and taking their retirement in installments while they were young enough to enjoy it. My dad was at varying times a Rhode Island lawyer, real-estate speculator and boutique hotelier who lived, like Travis McGee, entirely by his wits. He and my mother were drawn to adventure.

One day they pulled my brother and me out of school to go sailing. We were gone for years. On a late September day in 1980 I took the bus to my public school in Newport, Rhode Island. I was in 7th grade, although only for about another hour. Nothing had been discussed at home about a departure. I had overheard my parents dreaming aloud about moving to Cuernavaca, a landlocked mountainous region in Mexico that you couldn't very well sail to. But that was it.

During homeroom, the loudspeaker crackled: “Adam Waldman, please report to the principal’s office.” The other kids, most of whom I would never see again, made hissing sounds. But I was a good student, and doubted I was in trouble. The principal shook my hand and wished me “good luck in Jamaica.” I nodded like I knew what he meant. Then I walked home. It would be nearly three decades before I actually set foot in Jamaica. “Jamaica” was simply what my parents, who had no idea where we were going, told the authorities because they had to tell them something. My parents were allergic to rules and authority figures, and school principals fit in that category.

A day or two later we set sail, aiming south. Our boat was a 44-foot sloop containing my until recently 3rd grader brother Matthew, two parrots, a large German Shepherd, and my parents. We had my cherished windsurfer and two black mopeds strapped to the deck, so we could get around wherever it was we were going.

These were the days before reliable weather forecasting. Off the coast of Cape Hatteras we were hit by a heavy gale and found ourselves crashing through 20-foot seas, with howling 60 knot winds in the dead of night. We lashed ourselves to the wheelbase so we wouldn’t be swept overboard by the wall of cold ocean smashing over the deck every 5 seconds. Our little 11-ton boat, the aptly named Whiplash, flew through the air off of every wave crest. But we rode it out.

It was the first of countless adventures, some more dangerous than others. I spent 3 years living and sailing around the Bahamas and Caribbean as an unschooled transient. Though it would be more accurate to say that we were not formally schooled.

It was also before school systems possessed computers. There was no “cloud.” When we returned home from hot climates, with carefully practiced tales of rigorous schooling, the school district dutifully promoted us to our age-appropriate grades. In the tropics I read any book I could find – philosophy, westerns, religion, history, fiction, poetry, fishing books – usually at the borrow a book/lend a book that existed ad hoc in many ports. I read half the day. But I did not do a single math or science equation from 1981-1984.

In the Caribbean we encountered horrific storms, tropical gangsters who wanted to steal our boat and leave us at the bottom of the ocean, and occasionally hostile locals. The waters of the Caribbean were the transit point at that time for about 75% of the narcotics trafficked between South America and the United States. Pleasure cruisers of families like ours happening onto drug transfers at the wrong quiet anchorage at the wrong time were going missing.

We had guns, big ones and lots of them, that needed to be pulled and pointed for defensive purposes from time to time. My father’s weapon was the Ruger Mini-14 semi-automatic assault rifle with banana clip, my brother or I were expected to handle the sawed-off Mossberg “Persuader” 12 guage pump action shotgun with pistol grip (“very convincing” said the accompanying literature), and my mother was armed with the Glock 9MM pistol. We had assorted rifles, and even a bow and arrow for the hands of whomever else was on board. Without exception, everyone who stared down the barrels of the Waldman family’s guns (we pulled as a group, all hands on-deck, and sometimes through the portholes too) chose to take their business elsewhere. It was a porcupine strategy, and those guns were the quills. The chilling part was our targets’ unsurprised reaction when the guns came out. You wonder about people’s intentions when you point a gun at their face to stop them from whatever they are about to do and their smirking expression says: ‘OK, not today.’

After one long night hunkered down in the lee of small Bahamian spit of rock providing a modicum of shelter from a ferocious storm’s wind and swell, a ratty 60-foot fishing boat mysteriously motored into the greasy dawn and began to circle us. One lone man was at the wheel on the flybridge, but we could see other men actively moving around down below through the portals. The man shouted over the gale, “Weesh way to Bee-mini?” He was asking us ocean directions in the middle of a storm. My father pointed south in the direction of Bimini. The boat manuevered closer and the man repeated his question over and over. People don’t ask directions at sea, not even on sunny days. My father animatedly pointed south again. The boat circled closer still, like a shark. “Guns” my father ordered simply, and out they came. The mystery captain smirked that smirk and motored off north into the storm.

One day in 1983 we sailed into Gustavia Harbor in the French West Indies island of St. Barthelemy, intending to stay for the weekend. We stayed two years. Wherever we were, my brother and I went out mornings to hunt in my little inflatable Avon speedboat. I had bought the Avon in 1980 from winnings speculating my summer earnings as a professional windsurfer on the price of gold Krugerrands, which rose sharply as interest rates and inflation soared. I made a small fortune by any 1980 teenager’s standards, enough to buy Awful Awful milkshakes at the local Newport Creamery indefinitely. But I was a Waldman, so I bought a boat.

My brother and I would anchor and jump off the Avon to shoot grouper or lobsters with a ‘Hawaiian Sling’ (a simple steel spear through a hollow piece of wood launched by a rubber band slingshot you pulled back past your ear) while keeping an eye out for sharks after there was blood in the water. We also hunted for conch, a beautiful and tasty mollusk that we dived down and picked up off the seabed. When we were unsuccessful there was canned, slightly rusty Dinty Moore beef stew in our boat’s midlewy hold. It presented strong encouragement to catch our food.

In St. Barths my parents become close with the local riff raff. This included the singer Jimmy Buffett, who was in the midst of espousing in song precisely the escapist island lifestyle my parents were pursuing. Buffett frequently brought his guitar to our boat and sang songs like “We Are the People Our Parents Warned Us About.” I once woke up at 3 am to use the head, and found Mick Fleetwood, the drummer from Fleetwood Mac, wandering around the deck repeating his own name in a dull-normal voice – “Michael John Kells Fleetwood” – mantra-style. It became a family joke – we would sometimes spacily repeat his full name while playing air drums.

Our crowd also included St. Barths’ local industrialists: the mustachioed, hippy, amateur marijuana smugglers who plied their trade in the days before cartels. They wore gold chains, Hawaiian shirts, and short Sundek bathing suits. None of these pirates had real names, but only smuggler handles like “Flash,” “Crazy Willee,” “Diver,” “Finland,” “Mr. Moon,” and “Little Jon.” They hung around partying and waiting to do the job they did just once a year – load their pay-no-attention-to-this-boat to the gills with marijuana and make the run across the Gulf Stream to Florida or the Carolinas. We all lazed around, drinking minature “greenie” Heinkens, playing softball on Shell Beach and listening to Buffett, who lived vicariously through these amiable criminals waiting to make their run. Buffett chronicled the exploits and philosophies of these interesting soundrels in song: “I got to go fishing, I’m down to rock bottom again … Just a few friends.” “Fishing” was the smuggling run to Florida; “rock bottom” meant out of money, time to go to work with “just a few friends” whom you trusted. Eventually, the luck of every one of these grass-adventurers ran out and they went to jail. It was their cost of doing business.

My father, inevitably, became their lawyer.

My brother Matthew and I had our left ears pierced by one of the smugglers sitting on St. Barths’ main bar Le Select with a big number 16 sail stitching needle pushed through our earlobes and into a cork from a bottle of Chateau Margaux. Matthew was 9 years old, and he also sported a gold necklace, Hawaian shirt and short Sundek bathing suit. We were not rich. In fact, other than the occasional fruits of some entirely impossible to count on economic success, expended as grandiosely and quickly as possible, I suppose we were often relatively poor, living among and like drug smugglers. As Buffett sang, “I’ve done a bit of smuggling. And I’ve run my share of grass. I made enough money to buy Miami, but I pissed it away so fast.”

When my father ran out of money every few months, just like the fictional Travis McGee or the smugglers, he would have to go fishing, returning to Rhode Island to settle a case (he was and still is at 84 years old a practicing lawyer) or sell one of the small real estate properties he owned. But the French franc was 9 to the dollar, a cheeseburger in paradise at the hippy smuggler hangout Le Select cost a buck, Dom Perignon was $15 a bottle, and my brother Matthew and I generally caught our own dinner. Plus we had a free water view.

My parents and brother spent two more years living the gypsy life once I checked myself at 15 into an English Public School, after sitting on deck reading an interesting 1920’s Evelyn Waugh book mocking English Public School, against my parents’ howls of protest. I did not know a soul in the whole of England. But when someone taught our parrot to incessantly say “motherfucker,” I knew it was time to go.

My departure created an open cabin, a quarter berth that was about the width of a sleeping bag. This made room for my brother’s “topless tutor” Marianne, the semi-solution to his lack of education. There is a photograph of my 9-year old brother, with a big gold pirate hoop earring, “reading” a geography textbook with his topless tutor. The book, alas, is upside down.

It was an adventurous way to spend my formative years. I remain grateful to my parents for that bohemian rhapsody, which taught me individualism, self-reliance, and how to roll with the seas. It nurtured that best human trait: wonder. I was exposed in equal measure to the transient lifestyle and the schemings of outlaws; those men and women who lived outside the mainstream and looked down on those who lived inside. It taught me flexibility and adjustment. It planted a seed of mistrust and disdain for the Establishment.

But the teenage Kruggerand buyer prevailed in the war against the beach bum in me. I went to law school and chose to slum for nearly a decade in the very Establishment I was raised to renounce to get where I needed to go. As a Washington lawyer, my corporate clients would never have guessed my formative years were spent without shoes, shampoo, hot water or school, in the company of drug smugglers.

I worked 14-hour days, 7 days a week at a blue chip law firm called Wilmer, Cutler & Pickering, and then as a Clinton Administration political appointee at the US Department of Justice. Law was pulling out the guns when the bad guys came in the night. It was bloodless combat, and a way to make a difference for a client or a country. I had read dozens of books about heroes and crooks and learned much from both of their styles.

Law is also about appearances. So I studied and then feigned conventionality. I wore Hermes ties (I found 20 at a yard sale and bought the lot for $10), horn rimmed glasses, Prada suits, and English shirts with different colored collars and cufflinks. I considered suspenders. I built a Washington network. I practiced law mentored by former Governors, White House Counsels to Presidents and FBI and CIA Directors, and sponged up their knowledge and strategies. And the second I believed I had learned enough practicing law in the big leagues of Washington, DC at the foot of the legal eagles of that time, I thought I was ready to go do it by myself.

Which I was not. It’s called “practicing” law for a reason. But ignorance is one of the advantages of youth.