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I’ve been carrying around the same twill, olive-drab briefcase for almost 31 years. Mostly for business, but sometimes for vacations and weekend excursions. Heck, the darn thing’s perfect for all the activities I’m generally into. I can set it down on the dock between my feet at boat shows and, like magic, I’ve got myself an instantaneous little filing cabinet from which I can pick and choose conveniently. On boat tests, the bag protects job files and equipment from saltwater and stands upright if shoved under a seat or stashed in a locker. And during other jaunts (whether for fly fishing, cruising, vacations afar or work-related extravaganzas) I can’t tell you what a loyal, comforting companion it’s been over the years.

Bill & Old Bag

Back in early 2003, for example, just after the second Gulf War began, I stowed it, chockablock with notebooks and camera equipment, under a webbed jump seat in an antique Navy helicopter whirring north to the coast of Iraq to do a story on the U.S. Coast Guard’s presence there. Earlier, on a dark night in 1998, it kept my computer dry while I stood alone in the rain on a dirt airstrip behind a jungle airport outside of Alotau, Papua New Guinea, waiting for a jeep ride to a circumnavigating yacht loaded with divers, scientists and adventurers. Even earlier still, it dutifully carried my precious visas and other paperwork during long, heartbreaking trips to Cuba, the first one in 1992, when Fidel Castro’s heavy hand still held its iron sway. And just recently, it served as a very welcome pillow on a wild-and-crazy, hell-bent-for-leather delivery trip I did from Galveston, Texas to New Orleans.

But here’s the deal these days—the ol’ briefcase is getting just a tad worse for wear. On one side, just above the attachment points for one of the bridle-leather handles, the fabric is significantly torn and discolored. Moreover, the corners are blown out and the edges are fraying to a frazzle. You’d surmise from this, I suppose, that I should buy a new bag, something that looks stylish and fresh as I continue to roam airport concourses hither and yon. Something that looks somewhat more civilized and appropriate for polite society. More with it, more contemporary.

“Wow,” an unabashed frequent flyer commented recently. “You need a new bag, man … that one’s gonna fall apart on yah.”

But hey, I don’t want a new bag. Not now or ever. Me and my oldie-but-goodie have a history together. We’ve been through thick and thin. And an ounce of shared experience, for my money, is worth a ton of pricey, brand-new twill, rivets, thread and bridle leather.

I’ve got similar sentiments, as a matter of fact, concerning the boat I presently own—the Betty Jane II. Sure, Betty’s decades old but, at this point, given all the time we’ve spent together during her lengthy, deeply-involved, two-year restoration, I would not even consider trading ‘er in for a newer, more stylish model. Not now or ever.

Betty’s a classic. A class act. Indeed, I’ve just secured some official paperwork that will confer antique-boat status upon her in the near future. There is, I believe, something noble about an object—a bag, a boat or anything—that serves and prevails and continues to serve and prevail despite the vicissitudes of history.

So yup, I’m launching another restoration, somewhat like the one Betty and I’ve just completed. I’ve tracked down a lady in a little canvas shop out in the Seattle area who says she can address the holes, rips and tears in my old briefcase using the same twill as the original. The repairs, she tells me, will entail some patches here and there, and quite likely they will not be absolutely discrete. New fabric looks different than old, weathered stuff.

“It won’t be perfect,” she confides. “But it will be serviceable, and it will last you many more years. You’ll love it.”

And I’m sure I will. Love, after all, is what an old, well-travelled briefcase, like an old, well-travelled boat, deserves.

This article originally appeared in the January 2019 issue of Power & Motoryacht magazine.