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I, too, am from someplace else—Maine, as I said, specifically Portland, which is directly connected to Key West by U.S. Highway One, or by a cruise up the coast, but Portland is as far from here as Pluto is from the sun. FYI, I spent five years in the U.S. Army as an infantry officer and got blown up in Afghanistan. That’s the short story of how I wound up here. The long story is a long story, and no one in Key West wants to hear long stories.
Freaks, geeks, loveable weirdos, and a few Hemingway look-alikes. He used to live here, and you can see his house for ten bucks. You can see mine for free. Bring a six-pack. Anyway, Key West’s official motto is “One Human Family.” Well, they haven’t met my family. And they haven’t been to Afghanistan to see the rest of the human family. Or, like Jack, to Vietnam. Or if they have, they’re here, like me and Jack, to float in a sea of alcohol-induced amnesia. I’ve been here four years. Five is enough to forget why you came here. After that, you’re not going home.
This is paradise. Better than two tours in Allfuckedupistan. Better than freezing my ass off in Maine. And definitely better than 23 Wall Street, where I worked for a year after graduating from Bowdoin College. If I’d stayed with Hamlin Equities I’d now be dead from boredom.
Being captain of your own fate doesn’t mean you always make good decisions.
“There is a fishing tournament, sailing from here to Havana in a few weeks.” “Does the Cuban Navy know about this?” He smiled. “This is an authorized event, of course—the Pescando Por la Paz.” He reminded me, “We are normalizing relations. The Cuban Thaw.”
The Cuban Thaw. The Key West Chamber of Commerce even had a new slogan: “Two Nations, One Vacation.” Catchy. But not happening yet.
“There are some other details you need to know.” Well, I was afraid of that. “Look . . . Carlos, I do charter cruises. Fishing, sightseeing, sometimes a party cruise. I guess I can do a tournament—even to Cuba—but I don’t do other things. Understand?” Carlos didn’t reply and his silence said it all. “But thanks for thinking of me.” I asked Amber to give the bar tab to Carlos and I wished him a safe trip back to Miami. He replied, “Two million.” “Excuse me?” “You heard me.” I said to Amber, “Hold that tab.” I said to Carlos, “Let’s get a table, amigo.”
Close by was the Zero Mile Marker for U.S. Highway One, the literal end of the road that started in Maine. I’ve had a lot of profound thoughts about that, usually fueled by a few beers. And I just had another thought: A journey of a hundred miles to Havana begins with a single misstep.
He liked to say he came back from Vietnam the same as when he left, which, according to my mother, is unfortunately true. Regarding war, the MacCormicks have fought for their country since they arrived in the New World in the early 1700s, killing Indians, Frenchmen, Brits, Confederates, Germans, Japanese, and assorted Commies without regard to race, religion, or ethnic background. My older brother Web fought in the second Iraq war, so we also have dead Arabs on the family hit list, and I knocked off a few Afghanis to ensure true diversity. But if you met my family or knew my ancestors, I’m
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My mother, June, a Bedell, is a third-grade teacher at a private elementary school, though she doesn’t particularly like children, including maybe her own. Most of the MacCormicks and Bedells are college grads and according to my father the youngsters have all been educated beyond their intelligence. He may be right.
As for me, I am apolitical, and as for Yankee frugality, I missed that class. If I had, for instance, two million dollars I’d buy drinks for the house at the Green Parrot and take Amber on a long cruise. My financial advisor is Jack Colby, who likes to say, “I spent most of my money on booze and broads and I wasted the rest of it.”
My father, of course, thought I was making a bad investment, a bad career choice, and an immature decision. I knew he was right, so I went ahead with the deal.
When I was there, it was ranked the fourth best liberal arts college in the nation, but more importantly the second best drinking college. We got beat by Dartmouth, though I don’t know why. I did my part.
Or . . . I could listen to what Carlos and his amigos had to say. As I used to say to my men, you gotta die someplace. And Cuba was as good a place to die as Afghanistan. And maybe that was better than wasting away here in Margaritaville, or on Wall Street, or in Portland. Lots of options. None of them good. Except maybe the Cuba option. Maybe this was my lucky day. Maybe not.
Jack always wore jeans and sneakers, never shorts or flip flops, and today he’d chosen his favorite “I Kill People” T-shirt. I suggested, “The Maine T-shirt I gave you would be good tonight.” “Yes, sir.” He doesn’t mean “yes,” and he doesn’t mean “sir.” He means “Fuck you.” Sometimes he calls me “Captain,” and I never know if he’s using my former Army rank or my present title as a licensed sea captain. In either case he means “Asshole.”
“You are an officer and a gentleman by an act of Congress, but an asshole by choice.”
“She’s a Cuban American lady. And what do you care? You’re so fucking old, the only thing you can get hard is your arteries.” Jack laughed. “Yeah? And I think you spent too much time in the foxhole with your gay soldiers.” I think we’ve been together too long, and I notice that when I’m around Jack, I use the F-word more than I usually do, and I mimic his wiseass attitude. I hope he’s not rubbing off on me. I’ve got enough problems.
“You been to Cuba?” “Hell, no. Place sucks.” “Could be interesting.” “Yeah. Like ’Nam was interesting.” He remembered something and said, “Hey, I saw a great T-shirt on Duval.” He smiled. “ ‘Guantánamo—Come For The Sun, Stay For The Waterboarding.’ ” He laughed.
Jack asked, “Where are these Beaners?” “Jack, for the record, I think Mexicans are Beaners.” “All these fucking people are like, mañana, mañana.” “No one around here is good with time, either, including you, gringo.”
Jack’s world view and prejudices are a generational thing, I think, and he reminds me in some ways of my father, who grew up in what amounts to another country. Jack Colby and Webster MacCormick are unknowable to me because their screwed-up heads were screwed up in a screwed-up war that was different from my screwed-up war. Also, I had the impression from both of them that they’d like to go back to that other country. My generation, on the other hand, has no nostalgia for the past, which was screwed up when we arrived. In any case, as my father once said to me in a rare philosophical moment,
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Jack and I simultaneously reached out to help the attractive young lady aboard. She had nice hands. I pictured us together in Havana.
Time, tide, and sunset wait for no man, so I told Jack, “Cast off,”
In my infrequent dealings with Cuban Americans, I’ve learned that “Communist bastards” is one word.
She still seemed a bit reserved, but she liked a good cigar, drank straight rum, and wore a baseball cap. She’d also slipped off her loafers and was barefoot. Jack says that women who go barefoot are hot. Sounded plausible.
Revolutions usually replace one group of incompetent autocratic assholes with another, and the real losers are everyone else.
“The devil is in the details.” “It always is.”
There’s a saying—‘I’d rather regret the things I did than the things I didn’t do.’ ” “I actually regret both.”
Jack lit a cigarette and pushed forward on the throttle. “Trust your instincts, Mac.” “My instincts tell me you don’t know what you’re doing in that chair.” “For half a million, I can learn fast.” “I need your decision before we dock.” “What do I need to know before I make a decision?” “Nothing you don’t already know.” “Okay. I’ll think about it.” He reminded me, “We’re on borrowed time anyway.” Indeed we are. And there was a payment due.
Jack asked, “Do you know how they begin a fishing tournament in Cuba?” “No. How?” “On your Marx, get set—go!” He laughed. “Get it? Marx.” “Pay attention to the depth finder.”
She smiled. “Secret missions begin with boring details.” “It’s good when they end that way, too.” She looked at me. “This will go well.” That’s probably what they said about the Bay of Pigs Invasion. Not to mention the CIA’s hundreds of attempts to kill Castro. And let’s not forget the Cuban Missile Crisis, the Mariel Boatlift, and the trade embargo. As Jack might say, the U.S. and Cuba have been fucking each other so long that they both must be getting something out of it.
Before you go on any mission, you need to understand what you know, identify what you don’t know, and try to guess what could go wrong. And finally, getting there is only half the fun; you need a clear path home.
Yalies, like vampires, can recognize one another in the dark. Similarly, Bowdoin alums can recognize one another in a bar—they’re the ones passed out on the floor.
back to the travel packet. I read: Each day has been structured to provide meaningful interactions with Cuban people. Which reminded me of one of Jack’s informative T-shirts: “Join The Army, See The World, Meet New People And Kill Them.”
“Just thinking about my vacation.” “Where you traveling to?” “Cuba.” “Why do you want to go to Cuba?” “North Korea was sold out.” “Really?”
I’m not a big fan of group tours—I did two group tours in Afghanistan.
Or, as I used to say to my men on the eve of a dangerous operation, “Tomorrow is going to be the longest or the shortest day of your life. It’s up to you.” And, of course, it was up to the enemy, and the gods of war, and fate.
She was young enough to be his daughter, but there was no physical resemblance, so she must be his wife. Cindy was a looker, and I wondered what she saw in him. Probably the bulge in his pants—the wallet, not the crotch.
The Communists, like the radical Islamists I fought, are not fun-loving people, and when they take over, they become the fun police. I once told a captured Taliban fighter, through a translator, “Life is short, sonny. Get laid, have a few laughs and cocktails, and dance a little,” but he had his own agenda.
As for my departure info, I wrote my return flight number and departure date—though I reserve the right to escape earlier by boat, under fire. I signed the form.
Our Cuban guide would join us at the welcome dinner at our hotel and answer any questions we might have about Cuba. Question number one: How do we get to Paris from here? The bus was comfortable, made in China, and fit for Americans, though the lavatory was temporarily out of order and would probably stay that way until a plumber arrived from Shanghai. This was Tad and Alison’s second trip to Cuba, they told us, though not together. I hoped they’d hook up and made themselves scarce.
So here we were in hell. There’s a TV series that documents the story of ordinary people who agree to smuggle drugs into or out of some shithole country. They get busted, of course, and I used to laugh at the stupidity of these amateur drug smugglers who risked ten or twenty years in a hellhole third-world prison for a few bucks. What were they thinking? I would never do anything like that.
Our first few hours in Cuba were proving to be a challenge for the less hardy souls, who probably wouldn’t sign up for the Yale educational trip to Afghanistan.
I’m all in, as we used to say in the U.S. Army. Good to go. Sex, money, and adventure. Does it get any better than that?
Anyway, about half the group seemed normal and the other half needed more mojitos, or an enema.
I had the daily itinerary in my pocket and
unfolded it on the table. I read: Hemingway’s house is just as he left it in 1960. Probably because the Commies wouldn’t let Ernest take anything with him when he left. After Hemingway’s house, we’d go to lunch, then a visit to Vivero Alamar, a co-operative research farm where we’d learn about growing organic food. I wondered what sadist put this together.
I noticed that Antonio was not in the room to monitor Tad’s lecture for subversive material, so maybe he was busy reporting me to the secret police for questioning the weight of F.C.’s marlin. My mouth sometimes gets me into trouble, which makes life interesting.
There was no time for Q&A, but Tad remembered to give us the names of some good nightclubs, including Floridita, the birthplace of the daiquiri, and where Hemingway used to hang out. Tad said, “His record was eighteen double daiquiris in one sitting. Don’t try to match that.” I said to Sara, “We used to do that before breakfast at Bowdoin.”
time to take pictures. I could imagine the slide show conversation back in the States. “And those two hot tamales ran off together, and we all got questioned by the police and missed our day at the tobacco farm.”
“I assume there are patrol boats out there.” “There are. The Guarda Frontera—the border guards. They keep an eye on the commercial fishing fleet and also look for the rafters. But they can’t patrol hundreds of miles of coastline.” She added, “About five or six thousand rafters a year try to escape, and fewer than half are caught.”

