Richard Cleaveland

February 22, 2010
Richard Cleaveland, webmaster, uses his electrical engineering expertise to manage the Dewey Beach website. NONE ROB KUNZIG PHOTO

Richard “Dick” Cleavland jokes that he may be the oldest webmaster in the country.

It wasn’t a job he applied for, Cleaveland said, but when the Dewey Beach Civic League asked a volunteer to run their website, he knew he was the obvious choice. He’d made a career out of computers, and the town could use his tech savvy.

Born in 1926 in Milwaukee, Wis., Cleaveland was a geek before the term existed. He tinkered with ham radios before graduating from high school in 1944, when the United States was embroiled in World War II. The U.S. Navy was eager to snap up recruits with electronics skills, but Cleaveland’s career almost stopped short when he flunked a test for colorblindness. Presented a field of colored dots, he couldn’t discern the hidden letters.

“The recruiter told me to sit down, relax my eyes,” he said. So he did. He heard dozens of recruits pass by the screening table, rattling off the letters. His second attempt met with success.

He called his time in the Navy unexciting. As the war ended in twin mushroom clouds over Hiroshima and Nagasaki, Cleaveland was working stateside as a radio operator. His service earned him a free education at Northwestern University in Chicago, where he studied electrical engineering.

When he signed on with Philco, a Philadelphia-based pioneer in radio and television, the company assigned him to provide technical support for aircraft carriers stationed in the Mediterranean. With a home port in Cannes, France, Cleaveland spent six months hopping from ship to ship, enjoying the comfort of an officer’s billet and strolling coastal cities at will.

Cleaveland eventually moved to Alexandria, Va., with his wife, Barbara, a nurse. He worked for the Defense Communications Agency, building war rooms for the U.S. Air Force. The rooms full of screens, keyboards and displays absorbed and synthesized enough data to make even the most hardened geek swoon, but Cleaveland made a career out of assembling the systems and managing the flow of information. He worked until 1986.

Retirement suited Cleaveland. He patrolled the Chesapeake, hunting striped bass and bluefish on his boat, Alpha. He and Barbara would occasionally hop across the bay to Dewey, where they bought an oceanfront home on Bellevue Street. Cleaveland had a commanding view of the shore, where he watched dogs gallop freely along the tide line.

“They socialize so nicely,” he said. “Nicer than people. They’re so enthusiastic about meeting each other.”

Cleaveland was less enthusiastic about meeting a drunken tourist. The confused partier stumbled into Cleaveland’s home one night, asking if he had found his hotel.

A fence solved this problem. Otherwise, Cleaveland has gotten along well with his neighbors. He joined the Dewey Beach Civic League – and inadvertently began a second career. The civic league needed a webmaster. When no one raised a hand, Cleaveland bowed to the inevitable.

“Well, if no one else was going to volunteer, I figured I knew a thing or two,” he said. Cleaveland ran a few personal websites, including, where he posted genealogical research and his graduating class newsletter.

It wasn’t long until Dewey officials approached him about managing the town’s website. He was happy to offer his skills pro bono; however, he said, they insisted he accept some sort of payment.

Cleaveland gave in – sort of. For two years, he earned $1 a month. His contract has since lapsed; he doesn’t intend to renew it.

While he lives at the Cadbury retirement community in Lewes, Cleaveland keeps his property in Dewey and continues to work on the website. His youth was preoccupied with building circuits and fiddling with wires, but Cleaveland said he’s now more intrigued by the abstract side of information – databases, websites that exist only as fields of numbers.

When Mayor Rick Solloway suggested broadcasting council meetings to the website in December, Cleaveland began experimenting with streaming video files. With two meetings successfully broadcast, Cleaveland said he’s quite happy with the results.

“Boy, have I learned a lot in a month,” he said.

A knack for electronics doesn’t keep Cleaveland glued to a screen. He and Barbara have embarked on two road trips to Alaska, driving to the nation’s frontier in a motor home.

They made the first trip even longer via New Orleans and California to visit family. On July 27, 1991, Cleaveland celebrated his birthday at Point Barrow, the northernmost part of the United States.

“It was snowing. There was ice on the water,” he said. “It was colder than hell.”

The final mileage, driveway to driveway, was 16,848. Like technology, Cleaveland said, travel keeps you younger.

“It keeps him out of trouble,” Barbara said. “Sometimes.”

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