The End Game

Poets often write about the joys of falling in love—they seldom mention the painful break-ups that invariably follow.

I couldn’t process what I was seeing—a sparkling 1960 Ford Galaxy pulling to the curb in front of Slip #7, Vinoy Basin, St. Petersburg, Florida. It was nearly sixty years ago. I was twelve years of age. My frail father visibly shook as he came out of the car, whether from rage, shame, or his Parkinson’s I cannot say. 

Fatty and his sister on the bowsprit of Elizabeth in New Orleans circ. 1955.
Fatty and his sister on the bowsprit of Elizabeth in New Orleans circ. 1955.

“It’s done,” he said to my sisters Carole and Gale, to my brother Morgoo the Magnificent, to our mother Marie; to me. “She’s sold.” 

He spoke softly so our family schooner Elizabeth would not hear. 

He leaned on the car for physical support. 

Sold? That was impossible. We were headed for Tahiti. We were sea gypsies. We shunned the shore. We chased the horizon. Our job was to avoid the greedy dirt-dwellers, not linger nor luxuriate amongst them. 

What kind of BS was this? Ashore we were round pegs in square holes. We didn’t fit, not at all. It wasn’t our world. I didn’t feel as if we were moving off our floating family home—I felt a part of me was being forcibly amputated, that I was being forever diminished. 

I remember thinking “…no, please God no!

The sky spun. I felt dizzy. My mother caught me just in time—before I banged my head on the concrete sidewalk.

“Get your stuff,” my father said, intentionally not looking at Elizabeth. “We’ll head direct for Chicago after getting gas—I just had the oil changed, checked the tires, topped off the radiator.” 

We were being thrown out of the Garden. Reality was rearing its ugly head. I wanted to scream—perhaps I did. 

At one point, everyone stared—reaching out to me like twisted, compassionate zombies. 

I turned and stumbled towards the Elizabeth. I didn’t see a half-rotten hull with patched cotton sails—I saw 68 feet of deflating oceanic dreams. 

I saw hope die. 

We’d failed. 

We set out for Paradise in 1953. We’d stoically endured the decade long pain of rebuilding her—all those steam-bent mahogany planks, those laminated oak frames, those tree-nailed Elm butt blocks; miles of caulking; endless days of sweat-drenched drawspoke and adze. “Built out of chaos, brought to law,” wrote sailor/poet John Masefield. And now it was all for naught. 

We’d sold her as if she was an inanimate thing to be discarded, to be callously traded for mere shekels. 

It was like discovering my family were slave owners and I’d never really known. 

I trudged through her varnished teak-and-holly interior to the forepeak. I was damp eyed. It was here, sandwiched between my tomboy sisters, that I’d spent each evening of my happy existence. I could smell the hemp of the anchor rode, the tar of its marlin, the turps of her hull’s seam compound. A ship’s clock chimed aft. A halyard tat-tat-tatted against a solid Spruce mast. A bulkhead creaked. A shaft of sunlight from a hatch illuminated dust motes. A horrible realization slowly crept over me. Just as life could be idyllic with horizon-wide expectation, it could be hopeless with narrow despair as well. 

I took nothing. I couldn’t bear to pick over her carcass.

Thus, my entire childhood remembrance was divided into light and shadow: the happy part afloat in Mother Ocean’s sweet embrace—the miserable part ashore on the mean streets of Chicago. Ever since the mid ‘60s I’ve done nothing productive, really, other than attempt to stave off that gut-wrenching, sea-centric realization that I am unhappy where my species live. 

Suddenly, in scary Chicago, I was behind enemy lines. I was surrounded by greedheads and worse. Escaping the clang of a cash register wasn’t optional for me; it was imperative. This wasn’t a city, it was a concrete jail cell with rusty drains in the floor to allow the thick, criminal blood to run off.

Fatty and a girlfriend on Corina in 1968.
Fatty and a girlfriend on Corina in 1968.

At fifteen, I purchased my own boat, a rotten 22-foot Atkins double-ender. At sixteen, I snagged a girlfriend and left to tour the Great Lakes. Passing back through the Windy City at eighteen years of age, I snagged an Italian wife and waved goodbye forever as I went down the Mighty Mississippi River.

Elizabeth had been my Cradle of the Deep, now Corina was my long watery path to manhood. 

“You’ll see,” I told my young bewildered wife. “Mother Ocean will take care of us.”

Mother Ocean did. We flourished—from New Orleans to Miami, from the Bahamas to the Lesser Antilles, from Trinidad to San Blas. Rum was 82 cents a bottle—the herb was practically free. Why wear clothes? Why follow the rules of fools? Surely, no one with any sense paid attention to such tawdry laws, did they? Why not trust to Jah exclusively—didn’t he know, when we were truly hungry, to send fish to our dangling hooks?

Time went by until my ever-more-beautiful Madonna-of-a-wife asked, “Do you hear anything Fatty?”

“No,” I said. 

“I do,” she said. “My biological clock. It’s ticking.” 

that was a conversation stopper!

“Twenty-two feet is too small for a family,” I said cautiously. 

“How much does, say, a well-found 35-footer cost?”

“Too much,” I said curtly. “Ten times too much!”

“Then let’s build one,” she said, as if talking about a bird cage. 

“Ah,” I said, at a loss for words. She was a wonderful gal but she had no idea what she was saying. “Boats are complicated,” I continued. “Building one would take years.” 

“You could do it,” she said matter-of-factly. “We could do it.”

I said nothing. 

I believe in you,” she said softly. 

The moment she uttered those words, I knew I was sunk. 

First, we had to sell our beloved Corina. 

It didn’t take long. I sold her for eight times what I paid for her and half of what I had into her (not including our many years of labor, of course). 

But I was totally unprepared for the emotional gut-punch that parting with Corina entailed. Leaving the Elizabeth hadn’t been my choice and there had been a clear, definable reason for doing so—my poor father would wrestle with Parkinson’s to his grave. 

But this, the selling of Corina, was a personal choice—a cold calculation of my future over my vessel’s future. And Corina deserved better. True, I’d rescued her but she’d also rescued me from Chicago and childhood as well. And she’d never failed me. In the end, it was I who failed her. 

This is what happens when you love a boat. She loves you back. And you end up like lovers—mutely owing each other the inexplicable. 

Regardless, I felt like a cad walking away from Corina for the last time. Sure, the couple we’d sold her to were nice; but they had no sea-sense, only money and a bottle of sunblock. 

But we needed their cold-hard cash to build our dream boat, an Endurance 35 that we named Carlotta. 

Choices matter, especially difficult ones. 

My intention was to be merely cool-headed and pragmatic but the result was that I felt cruel, callous, and uncaring. 

I never heard from Corina again. That’s the way with spurned lovers, I guess—you can feel their bitterness down through the decades. 

Here’s a horrible fact: I almost never dream of my dearly-departed—not my father, my mother, and not even my beloved sister Carole. But I regularly dream of Corina and the Elizabeth—convoluted dreams of regret. They lurk in dark, scary sheds on abandoned farms—with only a stem that needs to be recaulked or a garboard plank that needs replacing. Surely, I couldn’t be so callous as to refuse a few minutes of my precious time, could I? 

I reveal these sordid facts not with pride nor shame but because they are true: a sailor never fully escapes a boat that has repeatedly saved his life. 

The closest I can come to a rational, shore-understandable explanation: I seldom promise people anything; I always promise my vessels everything (to motivate myself to climb the mountain of their maintenance)—and thus, somehow, I always fall short of the grandiosity of my watery vision.

I buried myself in work to forget.

Carlotta under sail in late 1980s in the Caribbean.
Carlotta under sail in late 1980s in the Caribbean.

We built Carlotta from a few sheets of paper over the course of six hard years. Calculating her cost was easy—every penny, every hour, of every long, callous-inducing day.

We lived in a chilly plastic tent beside her in an old leaky warehouse in Southie. Carolyn humped tables; we ate left-overs from Nick’s No Name on the Boston Fish Pier. We purchased our winter clothes at Goodwill—our boots at the Salvation Army. We walked the streets of Beantown—even bus fare was beyond us. In the winter, we had no running water, no toilet; occasionally, no heat in chilly New England.

On the positive side, the only way to stop shivering was to hug each other. 

And Carlotta was worth all the sacrifice—as was Roma Orion when she arrived a few years later. We sailed away from the North American continent forever—we happily lived solely in international communities of color for decades. Why? For the quality of life therein. Our self-built boat was our aquatic magic carpet—all we had to do was wish. 

…well, until September 17th, 1989, at 6:23 AM when a 72-foot schooner lived up to its name (Fly Away) and jammed itself athwartship across our bows at the height of Hurricane Hugo (a category 4) in Culebra, Puerto Rico. 

My cruising life has continuously offered me a stark choice—to continue to chase the horizon at great cost or live a life of quiet desperation ashore. 

I never considered shore. 

Actually, there’s nothing quiet about my life-long quest for personal freedom. I am king of my salt-stained world. I hold the tiller

Fatty bought Wild Card on the beach after Hurricane Hugo in 1989. Here it is being lifted back into the water.
Fatty bought Wild Card on the beach after Hurricane Hugo in 1989. Here it is being lifted back into the water.

of my existence fully in my own rough-skinned hands. Carolyn is my queen. My tiny vessel is our modest aquatic country. Our daughter is our sole citizen. Our fun-loving grandkids, the eventual deck rabble. 

Hell, no, I wouldn’t give up!

“When are you going to get it out of your system?” landlubbers ask me—as if cruising undersail was a particularly stubborn bowel movement. 

Money or prestige isn’t important in life—grit is. Grit is all—not education, not social status, not community standing. Only grit truly counts. I’ve already sailed through the Garden of Eden many times—of course I’ll never settle for less!

But, yes, it was hard to walk away from six years and 20,000 pounds of extreme sacrifice on the rocks of Culebra. And it took an additional decade to realize that Carlotta was just the physical manifestation of that sacrifice. What she really gave me as a man, was the knowledge that, with Carolyn’s help, I could do almost anything. 

So, yeah, I walked away from Carlotta—but I didn’t walk away from my defining dream. In fact, I embraced it ever tighter as I strolled the hundreds of wrecked yachts strewn on every beach in the Virgin Islands. 

There was a holed Hughes 38 awash at the entrance to Mary’s Creek on St. John—pounding itself to death in the surf at high tide. I knew the owner. I called him. “That thing almost killed me!” John Longhi screamed from his hospital bed. 

We owned Wild Card for twenty-three years, more than 100,000 ocean miles, and two leisurely circumnavigations. Initially she wasn’t my type of boat at all—too narrow, too small, too weak, too light in weight. Nonetheless, her S&S nobility and amazing sea-kindliness ultimately seduced me. She was totally game—around the Cape of Storms, across the dreaded Indian Ocean, through some of the largest waves the Agulhas Current could produce off the Wild Coast of Africa. 

But we eventually outgrew her. The beamy boat we needed to cruise aboard in our 70s was different from the narrow one we’d repaired on the beach while in our 40s. 

Nonetheless, I felt like a cad walking away from Wild Card for our third circ. We’d paid $3,000 for her salvage rights—that figures out to three cents a mile, initial cost. But I did walk away when an eager male Chippendale pole dancer (yes, life is weird) reached into his jock-strap and pulled out $30,000 damp dollars. 

I greedily snatched the sticky wad as I scurried away in shame.

Carolyn and Fatty on Ganesh under sail.
Carolyn and Fatty on Ganesh under sail.

Currently we’re in Southeast Asia aboard our fifth ocean-going vessel, a heavily-powered, French-built Amphitrite 43 we named Ganesh. We are in the middle of our fourth circ. I’m on my 61st year of living aboard. It is my fondest hope that, one distant day, the Good Lord allows me to broad-reach into Fiddler’s Green aboard her—and spares me the indignity of her gut-wrenching sale. 

Wasn’t life simple? 

Not just being incapable of following rules—being unable understand the need for rules! No, none of it was easy. Especially earning our living barefoot living in paradise. But my goal became clearer with each mile sailed: to remain the freest man in the universe; to be king of my tiny, waterborne country with Carolyn as my queen. 

Cap'n Fatty Goodlander
Cap’n Fatty Goodlander has lived aboard for 53 of his 60 years, and has circumnavigated twice. He is the author of Chasing the Horizon and numerous other marine books. His latest, Buy, Outfit, and Sail is out now. Visit: fattygoodlander.com