Curmudgeon seeks catboat for company and the occasional adventure

Bill Cheney’s Penelope, the catboat/muse responsible for this article. Photo courtesy Bill Cheney

Guest Perspective/Peter M. Winter

Because no one apart from me turns up on time these days I spend a lot of time waiting on my lonesome in bars looking at my phone while pretending to be someone with a lot of friends and an important life; and that’s how I stumbled across a report about a lunatic who recently spent $50 million on a used Ferrari. Well, a 1962 Ferrari 250 GTO to be precise. It was sold by some Microsoft guy for $48.4 million, I thought it would be even more startling if I rounded up.

This news got me to thinking about stuff I would never buy secondhand. Like, a mattress. A pair of underpants. Or those cotton wool buds on sticks that my brother-in-law the congressman uses to get wax out of his ears. Or a car. You know why I wouldn’t buy a used car? Not long ago I asked Google “are used cars hygienic?” and she came back with this, from the U.K.’s “Daily Express” newspaper: “Despite the proliferation of crumbs, stains, fag butts and hairs in our motors, we don’t like to actually clean our cars: indeed, it’s our third most hated chore, after cleaning the loo and clearing out gutters.” Given the dilatory nature of my fellow citizens in this fair land I have no reason to believe that the interiors of used vehicles here are any less revolting than those over the pond.

People who can spend that much on a used car are the kind of people who then spend many more millions to construct a private place to keep it safe from view. Oh sure, maybe once or twice a year they’ll drive it around the block just to remind people; but fundamentally this is a purchase that says “I have something and you don’t and you’re not going to get your hands or your peepers on it and that means I’m special.” You know as well as I do that most of our purchases are driven by what we think will make us attractive to members of the opposite sex, or the same sex if that’s your thing, but not these kinds of purchases. These are primarily about the need for what shrinks call “personal inadequacy compensation.” Kiwis like me have no need of such a thing, naturally, but it’s clear that many do, and not just Australians.

The disorder manifests itself in many different ways. For example, in recent years quite a few people have been investing in wine. I find this incomprehensible. If you own a $50 million car you can’t drive it to the store for a carton of milk. And if you buy wine as an investment you can’t drink it. How idiotic is that? You have to build an elaborate cellar under the stairs for the sacrosanct collection while you drink everyday supermarket plonk with dinner. I saw this very thing often when I lived in Atlanta, godhelpme.

Sailboats, of course, are different.

Sailboats are a secondhand merchandising category all to themselves.

For starters, you never have to worry about an owner with disgusting personal habits. The ocean will have licked his boat clean from time to time, and a good thing, too.

Oh sure, I know, there are a few lunatics in the sailboat category, too. There is nothing quite so uninteresting on God’s green earth as the guy hellbent on telling you how big his mast is (see above, re compensation) well, except for the guy who seeks to impress with stories of his derring-do on the briny; and then you watch him bring the sailboat up to the mooring and you know, you just know. So does his long-suffering spouse, up there on the pointy end, flailing around with a boathook in her nautical sweater and taking the blame.

But look, unlike a car or a piece of art or a wine collection, you can’t hide a sailboat away in a special place. It sits naked in the water, nude and vulnerable, exposed for all to judge. You can’t disguise its true character either, the way a realtor tries to do when she lights candles in strategic places around the house she is trying to sell, as if turning it into a shrine to Krishna will make amends for the fact that you never got around to fixing anything in the decades that you owned it.

So a sailboat makes manifest not just its own character, but the character of its owner. You can figure out in advance with whom you are dealing – and that’s critical. If I learned anything at all about sales, as I dodged and weaved my way through corporate life, it was that the first five seconds of any negotiation are the most important. With careful study of a sailboat you can get a bead on its owner and thus position yourself accordingly in the bargaining that precedes the handing-over of your hard-earned scratch.

A fake sailboat heralds a fake owner. When coupled with pretention, it’s deadly. This guy is a show-off, he never really enjoyed sailing; it was the accouterments he was after. He paid too much for the Beneteau in the first place, the depreciation is killing him, and he will be determined to recover all his money in order to spend it on his next big talking thing, which will be a Tesla or a robotic companion. Good luck dealing with him. How about a sturdy, old-fashioned wooden boat with beautiful, classic lines? This guy is a Connecticut Yankee or wants to be one. He has a Brooks Brothers jacket and a bow tie that looks like a monarch butterfly. He can tie it himself, too. You can strike a good deal for this chap’s delightful Herreshoff, especially if you drink a fair ration of martinis with him along the way.

See how easy this is? Have a shot at it yourself next time you’re wandering around the marina. You’ll find that the sailboat is more revealing of character and taste than any Facebook algorithm.

The other thing that makes the secondhand sailboat market different is the sheer variety of craft available. You can generally get your hands on exactly the boat you want. And so here we are, you knew if you played your cards right I’d eventually get to the point: let me tell you that right now I’m in the market for a secondhand catboat. It’s Bill Cheney’s fault. You’ve probably read his beautiful writing from time to time here in Points East. You may even have read his book, “Penelope Down East: Cruising Adventures in an Engineless Catboat” – if you haven’t, you should – but this guy has the life you want. He keeps one catboat, Shorebird, down at Beaufort, South Carolina, where he sails in the winter, and the other, Penelope, on Swans Island in Maine, for summer adventuring. Penelope has no engine. He’s a good man is Cheney, and in sailing with him I have learned the one absolute and fundamental prerequisite of catboat ownership: To be a successful catboat owner/captain /sailor, one must first be a curmudgeon. Not a nudge. Not a misanthrope. Not a cynic. Not a regular pain in the ass. A curmudgeon.

The first time we went out, on the Beaufort River, he flipped me the helm just as it was time to go about. I had no idea it was a test. Too casually, I pushed the tiller and slowly she came around. Too slowly for Cheney. “Having trouble finding the eye, Kiwi?” he asked. That’s when I saw why Cheney is a catboat man. They deserve each other.

That’s because the catboat is itself a curmudgeon. It’s a crusty, hard-bitten old thing, it has to be, given its mid-19th century antecedents as a lugger off the northern shores of Great Britain, where the waters are cold and gray and unforgiving. (This magazine will now be deluged with letters of protestation from catboat curmudgeons who will each have a different story about where the catboat comes from, thus proving my point about their essential nature). The catboat is optimistic, but it regards humanity with a knowing, jaundiced eye. It knows what it likes, and, more importantly, what it doesn’t like. It is authentic and honest and has no time for frippery. It believes that the greatest crime of all is the crime of taking yourself too seriously. It does not suffer fools and it will keep right on doing precisely what it wants to do no matter how hard you try to get it to change its mind. Best of all, it is dependable and reliable and when it gives its word it means it. Not bad. Not bad at all. I’d take it.

In fact, the sainted mother says she’s beginning to see signs of the curmudgeon in me. I take that as a great compliment, which may not be what she intends. She says I remind her of her Irish uncle, who apparently ended up forgetting everything but the grudges. And she says I no longer appear willing to keep my big trap shut for the sake of peace and quiet. But it’s not hard to understand, surely? At long last I know who I am and I know what I think, and I know what I want, and let me tell you, what I bloody well want is a catboat.

I hope you can help.

Peter Winter writes from his home on Georgetown Island, Maine. His short stories and political commentary can be found on