John Pollack can’t help talking in puns—no surprise for a past winner of the O. Henry World Championship Pun-Off. Ask him about Cork Boat—the tale of his offbeat effort to build a seaworthy boat from wine corks—and he talks about how he’s been “harboring” the idea for a cork boat since the age of 6. And about how working as a sailing instructor allowed him to “keep one foot in the water” while growing up.

Pollack, 38, grew up in Ann Arbor, Mich., son of a University of Michigan geophysicist who regularly took his family to exotic locales, many on the water. “I loved anything that floated,” Pollack recalls. He was also an inveterate tinkerer, and somewhere along the way, he came up with the notion of building a boat from corks—thinking he might launch it in one of his neighbors’ swimming pools. “My parents always encouraged creativity,” he says. “Nothing was too wacky to be considered.” So they started collecting wine-stoppers, one by one.

As Pollack proceeded through Stanford University, a stint as a freelance reporter in Spain, and campaign and speechwriting assignments for Democratic politicos, the corks kept piling up—about 3,000 of them, by the mid-’90s—but the boat never materialized. Then, in 1998, Pollack, then an aide to House Minority Whip David Bonior, found himself professionally disillusioned.

“I had a chance to do great things in Washington, but I wanted to see what I could get done when I put my energies towards something that was opposed by no one—something with no political agenda or purpose other than whimsy,” he says.

Pollack’s book details the effort by the author and a rotating cast of more than 100 Washingtonians to assemble a cork boat as cheaply as possible. (It ended up costing Pollack about $10,000 out of pocket.) He collected more corks from local maître d’s and bartenders; among the establishments he calls especially helpful were Restaurant Nora, Pizzeria Paradiso and, though it sells far more beer than wine, Adams Morgan’s Toledo Lounge. “Most people I approached were friendly,” Pollack says. “Half the people took me seriously, a quarter were enthusiastic, and a handful of those really came through.”

After figuring out a way to use rubber bands to bind together the corks—which were eventually augmented by donations from a California-based cork importer—Pollack and his team turned a Mount Pleasant group house into a factory. “I’ll be totally honest: There were long stretches where the boat was not fun,” he says. “It was a headache, a source of frustration…and there were periods where we wanted to quit. That’s where my stubbornness kicked in.” In October 2001, the team test-launched the Cork Boat—22 feet long, almost 5 feet wide and 2 feet thick, built from 165,321 bottle stoppers—from an Alexandria dock. It floated. In fact, it was so buoyant that it hardly dented the water.

The bigger challenge came the following summer, when Pollack’s cork-company sponsor offered to ship the boat to Europe so that Pollack and his friends could sail it 133 miles down the Douro River, which flows through the heart of wine country in Portugal—the country that produces more natural cork than any other. Though the Portuguese media—and local residents—were enthralled by the voyage, it proved to be no picnic. Pollack & Co. sailed into slack water and fierce headwinds, their trip mushrooming from a projected five days to 17—most of them requiring hours of monotonous rowing. Eventually, they crossed the finish line, though only with the help of a couple of tows through rough waters.

Pollack moved last August to New York City, where he works as a freelance speechwriter. The boat, for its part, remains in dry dock in the Portuguese village of Santa Maria de Lamas, possibly destined for display in a cork museum. “It’s in good shape and it’s seaworthy, but I don’t think it will take another voyage,” Pollack says. The sail on the Douro was a caprice that came together, “and to duplicate that would be impossible.” It’s the same approach Pollack took with the Pun-Off: After he won, he promised never to enter again. “There’s only one way to go after something like that,” he says, “and that’s down.” —Louis Jacobson